The baristas/service workers thing - nearly impossible to do smoothly. Especially tipped employees. If you live on tips, you can't afford to be cold. And if she can't afford to be cold, then you have no way of knowing whether her responses to your jokes, etc, are genuine. And if they're not, it's just terribly awkward.

However, baristas and waitresses have been known to hit on customers every now and again - so just be patient if you're unremittingly sprung on a girl in an apron.

On the other girls thing - if you're in a situation where your interaction, to that point, is in general conversational (flirting, joking, etc) - "I'd like to talk to you again...here's my phone number/email address/lame faceboook thingie"...if it's been non-conversational (dancing, etc), then, the classic asking out is entirely kosher.

Although, take this with a full packet of salt - I've mostly been in a position to be the girl-asking-guy-out, rather than the girl-responding-to-the-well-meaning-mack.

Sorry, no experience to help you out. Still, best of luck.

I know you primarily are seeking advice from women, and we could all use it, but let me suggest that we start by seeking "women" not "girls", and dates, not pickups?

The whole women/girl thing - I'm 26 years old, and I STILL have trouble referring to myself as a woman in a social context. So I think that's fine.

As to dates, do they happen anymore? In my experience, someone gets someone's contact information, things occur over a period of weeks, eventually meals are shared on the same days that nudity occurs, and after a bit, one of you wanders off or you start referring to each other as "boyfriend" and "girlfriend."

I don't know if I've ever been on a "date."

The barista thing was a total joke, hobolawstudent. Who are the lucky men to be on the receiving end of your advances and why aren't there more women like you around?

As for women/girl, dates/pickups, I have to agree with hobo completely here. If you notice in the post, I used the terms woman and girl interchangeably. I consider myself to be a guy/boy/man, whatever. There's no sexism involved, just semantics. I also have similar experience with "dates" as well, hobo. I was using the phrase "pick up" somewhat ironically, because it always reminds me of Larry from Three's Company and sleazy meat markets--though I guess the irony wasn't that clear.

This might sound lame, but hey, you say you're desperate... I have always thought it would be sort of romantic to get picked up in a bookstore. BUT NOT THE SELF HELP SECTION. If you see a cute girl browsing the isles, you could ask her for a book recommendation and strike up a conversation that way. If it seems to go well, ask her to get a coffee with you since most bookstores have those coffee stands in them. Offer the coffee as payback for the recommendation but make sure you buy the book she chose for you. Flattery... it goes a long way.

Hey, Jess. That's a pretty good idea, thanks. I usually try to pick up girls in the Psych section of the bookstore. I go for the crazies. I do strike up convos with women in bookstores occasionally. That's a good idea about offering a coffee.

And for all the rest of you....no idea is too lame (see my t-shirt idea above).

I've read Pride and Prejudice. I've also read Sense & Sensibility, Mansfield Park and Emma. Maybe if I carry and read all four simultaneously I'll have an even better chance. I'm thinking the subway might not be a bad bet...I live on the L train...lots of good looking gals on there.

Most of my experience with meeting new guys has been at clubs. And you seem to be up on the music scene. Have you thought of writing for a local zine? It gets you out of the house at night, and gives you a reason to be there at the club. It get your words out there with a byline and pretty soon you have friends you didn't know before.
FYI - they are waiting to be asked, and just as shy as you.

Mary Joan's advice is good, but if you want to meet a younger more modern woman, Twilight might be the book for you. But, this also could be a bit dangerous since girls under 18 are also reading this book like mad. Check ids before the coffee.

Wait a sec, Chris- you have no prob getting started, but it's just the getting of the number you're worried about? Good gravy. :D

Here's the most valuable piece-o-advice you'll ever get on this topic:

ASK FOR IT!!!

Okay, okay, takin' the smartypants off.

Why not try something low-pressure, like, "We oughta go do something sometime, you know?" If her response is an enthusiastic "Yeah, Chris, toootally! Let's!" you'll know you're home free.

If she's vaaaguely agreeable, and you're not sure about the signals, then suggest "trading" email addys rather than a one-sided number exchange. Again, less pressure just in case she's not yet convinced of your hawtness.

The key to it all? Act like you're totally cool and pleased with whatever her response is.

How's that sound, pastelito?

Okay, here goes....

1) Try out some hobbies. What do you like to do? Like to run? Like music? Like books? Like politics? Start looking for clubs that do what you're into. Why do I say this? Because not only will you be meeting new friends, you'll be meeting people that already share your interests, which means that if you do run across a girl you find intersting, there is a higher likelihood you'll have enough in common to make a go of it.

2) When it comes to the awkward moment of "asking out" nothing works like the simple truth. "Look I've really enjoyed talking to you, and I'd really love to take you out sometime." Honestly, women hear so many trashy pickup lines from people who think they are clever that the simple, straight approach is actually really refreshing.

3) Become the kind of person who strikes up conversations with strangers generally. Really, I tried this once, in a totally different context and got a really great date from the experience. I was in between careers and trying to figure out what i wanted to do with my life. So I decided I needed to find out what kinds of jobs were out there, so I made a point of striking up conversations with people whenever the opportunity presented itself with the purpose of finding out what they did for a living and whether they liked it. Planes, coffeeshops, bookstores, lines at the DMV. I made myself talk to people. Not just men who were cute, but everyone. Eventually, I got good at it, good enough that I turned a chance meeting with a cute guy on an airplane into a really great date. It didn't last, but that's a whole 'nuther issue.

4) Trust me when I tell you that before I met the hubby I dated a lot. Mostly I refere to it as the "cavalcade of losers" but what I can tell you from the experience is that people get really wrapped up in the notion that going on a date is such a big thing. They build it up so much in their minds that they paralyze themselves. You are asking someone to spend 1 to 3 hours with you in a public place for the purposes of talking and finding out more about each other. You are not asking them to be your sherpa as you attempt an assault on the peak of Mt. Evrest. My point is, relax. Put yourself out there. Don't worry so much about the fact that not every date will work out to something. Just flex the muscle and spend time with people until you find someone who you click with.

Good luck, Chris. I think you'll be fine.

Chris Kelley,
No need to carry around Jane Austen everywhere. Honestly if I saw a guy carrying around Jane Austen with him I might think he's trying way too hard or he's gay.

If you're genuine, it will shine through. If you've sparked up a conversation with someone and you want to ask them out, just be honest.

"Hey, I've really enjoyed talking to you. It's so refreshing to talk to someone witty and smart. If you'd like to get a coffee or bite to eat sometime, I'd love that."

She'll either say yes or no or I have a boyfriend or I enjoyed our convo too or something.

The contact info exchange will happen after that.

It's all about being able to read genuineness from someone. A smart girl will know a cheesy guy before he even comes over to her.

TRUST ME!

I met my husband online -- via nerve.com personals. That site is cool because it's an "edgier" crowd than on match.com and the like. Dating is so hard -- good luck to you! You should read mad_typist's posts on online dating. She has lots of good advice.

Definitely go do something you like to do! You will meet other people, women/girls and men/boys. The men/boys will possibly become friends who could introduce you to more women/girls. The bonus of meeting someone while engaged in an activity you like is obviously that she will like said activity as well.

If you're not shy, striking up a conversation while waiting at the checkout in the supermarket is a good idea. In NYC I'm not so sure that will work. I live in Boston now where you can do this without people thinking you're an axe murderer or a crazy stalker. When I lived in NYC in the 80s and 90s it was not so.

Good luck, it will happen if you let it!

Yes, you can meet people online. I did a series of posts on this:
Introduction
Part 1: Getting Started
Part 2: Setting Up Your Profile

I never finished it, because I didn't get much feedback, so I figured people weren't interested. Nonetheless, you may find some nuggets in there that will help you.

A few thoughts, Chris. I've seen these work for myself, and for friends and colleagues:

1. Be as handsome as you can be. You know what I mean.

2. Be clean and crisp. Sure, some women like grunge, some like disheveled, but you cast the widest net by keeping your appearance in fine repair.

3. Be fit. As a young man, you're rather expected to have a muscle or two (no bodybuilding, unless that's your thing), and to be able to run fast.

4. Have interests. Hobbies are a good way to connect with women, and they also round you out as someone with passions, even if your interests don't necessarily turn a particular woman's crank.

5. (This is important.) Have something to say. Knowledge, informed opinion and wit are the surest means to bringing a woman in for a closer examination, after she's noted approvingly your cute mug.

If you do these things, and you go to places where women are (we at Man, Inc. are building a real-time interactive map to track congregations of women - note: convents are marked in red for a reason)... then I'm confident that you'll find women of excellent compatibility orbiting you, as you orbit them.

Follow Man Talk Now's advice. He'll cast you his seconds, I'm sure. He's the George Clooney of OS (or Brad Pitt or, fill in the blank - you know what I mean).
You sound like you are articulate but perhaps a little shy. If you try online sites, post a picture where women can see your smile and your entire face (not your car or boat - please!!)
I f you meet someone that captures your attention and interest, just be honest about it! If you say, "I'm a little tongue tied or embarrassed to ask at the risk of sounding like a jerk", you will win more points than by just acting like a jerk. Rated for honesty.

This is what I've observed from the young men in my presence who seek relationships:

(1) Take MTN's advice ... all of those things are important
(2) You said, "I have no problem striking up conversations with women I'm attracted to and making them laugh, but I'm not so good at, ya know, getting a phone number or something. I just feel like I don't want a girl to think I'm a jerk, like I was just being friendly cos I want to get into her pants or something." ~~~ If you've closed that much of the deal, leave your number for her, don't ask for hers. Sounds egotistical, but it seems to work like crazy ... I don't know why. My godson swears by this. He never asks for a number (for fear of rejection) and he gets lots of calls. I guess it works like this ... if she's interested, she'll find you.

(3) I can tell you my daughter despises facebook stalkers ... this seems to be a no-no.

Good luck Chris ... I think you've got the hardest part squared away ... being charming and thoughtful.

Be friendly, circulate, mingle... go to gallery openings. Dress nicely. Be sociable. The Sierra Club has some kind of under-30 mingulation type of event. Do volunteer work. Have a party and invite everyone you know and have them bring people Meet new people that way. Take a new class in something interesting. It's hard not to meet people. I'd avoid bars and/or dating websites. Just get out there and live an interesting life and you will meet interesting people.

Volunteer. You'll meet people who have an awareness of others' circumstances, and if they're volunteering alone, they're likely to be single.

That sounds like pretty good advice, Mary Joan. So the chicks really do dig the Jane Austen, eh? Would throwing in Wuthering Heights just be gilding the lily? What aside from Austen works on a train? I mean, how could I approach a girl I thought looked cool?

Ardee, that's good advice, too, but I don't know of any local zines (it's NYC, so it's kind of different I think), and I really don't go to many shows, cos I'm just not that into it anymore. Sure, I saw Guided by Voices open for Pavement, but that was 1994, ya know? :) I have trouble remembering that girls are just as nervous, that it's kind of like a junior high dance where the boys are standing nervously on one side with the girls on the other side.

Jess, your advice totally cracked me up. Seriously. I was thinking maybe not checking ID or just not asking age at all, but I can see your angle, too. (I hope people reading me realize that much of what I write is for comedic value.) Btw, 3 questions: 1) do you live in NY?, 2) Are you single? (this is of less impor, 3) how old are-- Well, scrap the third one, I guess I only have 2 questions.

You know bees, if you would just take your (smarty) pants off, this wouldn't be an issue. :) I know, ask for it, ask for it. I do understand your advice, I just have trouble putting it into practice. Sounds like good advice, mon petit chou.

And as for Liz's helpful novella:
1) I'm an artist, I like music, I like politics, I like pugs (though I do not own one, so I think a pug club may see me as some kind of pugvert or pugophile). I'm going to take a photography class this spring, so that's should be a chance to meet people. I don't know many people in the NY/Brooklyn art scene, not sure how to remedy that.
2) Oh, I agree that the direct approach is best. But I'm not referring to just situations where you've had a long conversation. Maybe it's just 2 minutes. I think the bookstore to cafe advice was good.
3) I love talking to random people, just as you described. You can learn stuff from people from all walks. If I sense that a person standing in line next to me is friendly, I'll strike up a conversation. If I sense that someone is having a bad day, I'll try to make them laugh (often it works). As for meeting girls this way, there was a cafe I used to go to and at least a few times a week I'd chat with cute girls who came in (lots of babes went there), and one of the guys who worked there would ask me, "How do you do that? And how do you not seal the deal?" Exactly, my friend. How.
4) Trust me, I don't build dates up in my mind. On the few rare occasions that I have gone out recently, I had zero expectations. I don't paralyze myself--I like meeting new people, and I can talk to just about anyone for 1-3 hours, even the guy on the airplane who was a windmill farm contractor. My problem, Liz, is that I've been flexing the muscle alone (ewww, did I just write that?).

Hey Chris,
Women like being talked to, but just don't be creepy about it... know what I mean?
Also I agree with MTN's advice. Good grooming REALLY goes a long way and in my experience is vastly underrated by the male of the species. Manscaping not required - we like it if you wash your hair, wear clean clothes and clip your nosehairs!
And I've just recently stuck my toe in the online dating pool. For the most part it's a who's who of human crap, but there are some gems out there. The trick is NOT to go onto Match.com or Eharmony (arugghhhh!). Try Salon's personals section.... at least you know the type of girl that would post there probably is semi-literate, or she wouldn't have gone to Salon in the first place.

Good luck. Trying to date is such a drag!

A couple of suggestions --

As others have noted join a club or take a class. For example, take a couple of classes in sea kayaking. Or join a hiking club. Or go on a group bike ride.

Something I've noticed is that people tend to be attracted to others who are interested in people. That's something you can't really fake, but it is something you can work on. One time I saw a guy and girl who appeared to be out on a date, and the guy kept going on and on about himself -- his job, his plans, his interests, blah, blah, blah. WRONG. He should have been asking the lady about her job, her plans, her interests.

As far as the phone number -- why not just hand out yours? Write your home phone number on the back of your business card (if you don't have any get some made. If you are an artist you should be able to come up with something nice.) If you have had a pleasant exchange of words with a young lady say to her "I'd like to talk some more but I have to go. If you'd like to get together sometime and talk more, please give me a call." And hand her the card.

That way there's no threat. She doesn't have to express any interest or give out any information. You've taken the risk and expressed interest. You have presented an opportunity. The next step is up to her. If you don't hear from her all you've lost is a piece of paper.

sciencechick, I don't necessarily agree with your statement. I had a friend who met his wife on eHarmony, and he's a pretty decent fellow. eHarmony is nice because it serves a very specific function. It depends on the type of person Chris wants to meet, and the sort of relationship he's looking for (again, see my blog posts for my endless pontificating on how to do internet dating the right way).

Frankly, if I ever were single again, I'd probably go right back to internet dating, since it was the easiest method and I met a lot of nice people (not only as dates, but also as friends).

I have no problem striking up conversations with women...but I'm not so good at getting a phone number

Write your name and contact info down, hand it to her and say, "I like talking to you. Here's my phone number and email. I'd love to hang out again." Worst thing that happens is the same thing that's happening now; you never hear from her again. Or she might call. But you'd be surprised at how often women will reply "Why don't you just call me, instead?" and hand over their numbers.

I just feel like I don't want a girl to think I'm a jerk, like I was just being friendly cos I want to get into her pants or something.

Maybe she was only being friendly to you because she wanted to get into your pants? These are New York City women you're talking about, not nuns. Use your instincts and don't be afraid to be forward sometimes. Just ask her out already.

Online dating? Never tried it, but I know more than one married couple who met through online dating. So it clearly works for some people. If you're interested, go for it, I say.

Chris, I tollllllllld you the smartypants were off! *tapping foot* ;D

Since you're an artsy-fartsy dude, definitely check out FastCupid, aka nerve/the onion/salon/tantra personals. They will nickel and dime you to death for every little privilege, but there are some smart, interesting peeps (I used to blog over there).

Even more fun? OkCupid. It's an effin' free-for-all over there and it don't cost a dime. I usedta love that site when I was actively looking. And there are tests that are ridiculous and goofy to pass the time.

Got a laptop? I'll meetcha and we'll set up a profile and get you up and running.

Wow! You people are the greatest! So much good advice.
Stars, I hear ya about the Jane Austen/gay thing.
Amy, I did meet some cool people on Nerve like 10 years ago, but I think it's gotten kind of diluted. Back then it was mostly intelligent freaks, which I liked.
Singpretty, that's good advice. And, no, people are not scared of you if you talk to them in NYC in a deli or bodega or wherever...at least not noticeably. I had a lovely conversation about ginger ale yesterday morning with two nice girls at the deli I go to (one was rather fetching).
MadTypist, I think I read that when you first posted it, but I can probably find some new gems if I look it over again.
ManTalkNow: 1) check, 2) check, 3) uhhh...but not too bad, about average (I'm 33, not that young), 4) I have a ton of interests (music, film, art, sports, etc) and I'm an artist (though I'm not pretentious), 5) I always have something to say...and I'm always willing to listen to what the other person has to say. I can talk about the influence of Argento on David Lynch, or the erosion of civil liberties in the last 8 years, or the merits of old school Nikes.
Cartouche, I'm really not shy...only shy in the asking.
Irritated, I like that giving the number thing. I know a certain level of confidence is sexy. I've never tried to meet anyone on Facebook, so no worries there.
Gordon and High, you're both so right. I really should volunteer for something. Now what should it be?
Do you think I'm creepy, science? Maybe you're the creepy one.

Oh, you can get me up--and running--anytime, bees. Laptop or no.

I've date lots in the past. What the others said, including MTN is good advice.

Also, don't seem too needy. Be nice but not too nice. Have interests. Be open-minded. Give real compliments, not phony ones. Project strength mixed with sensitivity. Don't worry about it so much, that will show.

And what's wrong with going on the internet?

Chris, you don't say how old you are, but your comment about not having any single male friends makes me think you're probably in your early thirties, at that age where all your friends are suddenly married and socializing becomes a lot more difficult if you're single. If I'm correct, my advice is to focus on finding single friends and expand your social group rather than focus specifically on meeting women. Once you develop a social group and have more opportunities to go to parties/get-togethers/etc, you will meet women without even having to try. Honestly. NYC is crawling with women your age looking for a relationship. So sign up for some groups on Meetup.com and start asking guys on friend-dates -- once you have a circle of friends, the women will come along naturally.

Also, looking your best is a no-brainer. But this is tricky because girls like different things. For instance, I find clean-cut, preppy looking guys to be a huge turn-off. Other girls dig it. So find a female friend who's the type of girl you want, ask her what she thinks looks sexy on a man, and then try to fit that look.

I don't have any advice for you because I'm currently so obsessed with how i'm not dating anyone right now that I can't see past my own nose.
however, I have two things I do want to say...
1) DID NO ONE NOTICE THAT HE TAGGED THIS WITH "going blind"?!?! HAHAHAHAHAHA brilliant
2) I tried eHarmony and it was AWFUL. I tried craigslist and it was, well, bizzare although I got some great stories out of it and usually all I ask from life is that it be a good story to tell later. I am currently trying match.com.

I think the ultimate problem may be that I'm too lazy for dating in general. I like instant gratification. Also, thinking about meaning makes me tired, so trying to think about meaning(ful relationships) while dating is almost too much to handle.

Yes, the online thing can work. Being a good writer helps, so long as you use it to be yourself.

I've not lacked for company or relationships in 15 years of online dating. I've evaded marriage, but I don't see that on your list ...

Many many good suggestions here. The fundamental thing: picture in your mind the kind of woman you find interesting, engaging and funny. (Try not to limit yourself by fixating on height, weight, age, background, etc.) Now imagine where a woman like that--those clothes, those movies, those books, that sense of humour--imagine where a woman like that hangs out and does things that you also enjoy. Is there a cinema club? A running group? A particular cafe? A specific kind of music? And go from there...

I find myself dating a vast number of women who appear blissfully unaware of it.

M. Chariot, I have had a few relationships like that.
Kryptogal, I am almost 34, and I agree with your advice. But it's almost harder to make friends at this age than it is to meet a girl.
Dnelle, I'm glad you noticed my potential vision problems. You know what they say...I've tried CL some, once with great success (met a great gal that I dated for 3 years). And I've also gotten some really interesting stories out of it. Care to hear the one about the girl who informed me that my carrot allergy could be cured with the cleansing of a few high colonics? No, dear reader, I did not make that up, sadly. I like InstaGrat as well, and honestly, at the moment, I'd settle for mediocre sex with no meaning whatsoever.
Jeff, you are correct, you did not notice marriage. Marriage I actually would consider at some point. Kiddies? No. I've definitely had some luck online (and not all the weird stuff was bad weird stuff).
David, I can easily picture the kind of woman that I find interesting, engaging and funny...all I have to do is think of my ex-girlfriend. She was all of those things. We split up because she got a tenure track job in South Carolina--I moved down there from San Francisco, but it just wasn't going to work out. It was a shame.

Hey, check it out! All you have to do is bitch about your sex life and you, too, can be an Editor's Pick!

And the front page?!? Shoot, had I known, I would've started bitching sooner.

Chris Kelley. You're adorable and if I were in BNY, I'd certainly give you my number, but only if you weren't toting around Jane Austen books :D (J/K) In all honesty, you're probably the kind of guy we need more of in this world. I wish your type would come out of the wood works down here in Dallas.

If I'm understanding you correctly, the problem is 'closing' or getting a girls number, not necessarily meeting them. For most guys, it's the opposite, so you have to be well ahead of the curve.

A classic closing line is, "I've got to run, but how can we continue this conversation?" A girl that is dazzled by your rapier wit, love of Jane Austin and confidence will say 'that would be great, let me give you my number/email/whatever'. A girl that thinks you are a smug, pretentious jerk for carrying around a Jane Austen book will say something to the effect of, 'I have no idea'. Either way, now you know where you stand, but it's not an overtly creepy, loser way of asking her out (as you mentioned, hit me with your digits, etc.) or wimpy (giving a girl your number, they almost never call, at least in my neck of the woods-cold cold Boston).

My anxiety has always been based upon the initial approach, so if you have that down, you deserve all the congratulations in the world, as well as my envy. Best of luck, I think you may be pleasantly surprised at your results with that line...

Lay the foundation early. If you're getting ready to walk into a building at the same time as a woman, open the door for her. She'll probably remember, if it's an establishment where you're going to be spending time. I've never seen it done outside the South, so if it happened in New York, I would notice both that it happened, and who did it.

Also, remember, they're just as scared of you as you are of them, and their eggs are running out.

I vote (strongly) for online dating. When you're looking for a new place to live, you don't just saunter up and down the streets hoping one will leap out at you, do you? When you're seeking a car, you don't stand on the streetcorner, watching the traffic go by, hoping to see one that you like that's actually got a "For Sale" sign, right?

And when you do dive into that realm, Take some unsolicited advice from a girl who's been there, done that. A few times. All good.

Except the icky guy who was looking to swing, whose wife said she was sad I figured it all out before the coffee date. Yech.

my attention span as of late has been slim to none so im sorry if im repeating anything anyone has said, i just couldnt read everything already commented. *SIGH* too much time on my hands, not enough simulation.

Im sure you could meet a girl at a bar with out looking lame while being alone. Its the drunk jerks with their guy friends that piss me off at the bar. I hate the bar in general, no one is honest there.

I havent been in a relationship in about 3 years, why, the only reason I can come up with is my kids scare people off.. but Ive been chatting with people on sites like Okcupid.com and PlentyofFish.com you never know... maybe talking on line and getting to know each other will work for you better than the inperson way. People have a tendency to be more honest with strangers/people you havent seen in person before.

"Also, remember, they're just as scared of you as you are of them, and their eggs are running out. "

Mrs. Michaels, that is hilarious. You're twisted... into just the right shape.

An anecdote I hope will be a helpful one: Once I was asked out by my favorite bartender. We talked a lot when I came in and flirted. I think he almost asked me out a couple of times, and I'd been thinking awfully hard about whether I had the nerve ask him for his number in front of his coworkers and my friends. Finally, though, he wrote me a note and passed it to me with my change. He'd picked up a postcard (one of those advertisements they have in racks in bars and places) with a picture of a girl who kinda looked like me. He'd written something like "I like you and would love to take you to dinner" and drawn a black turtleneck sweater on the girl. I should add I have, like, six black turtleneck sweaters. He listed his email.

Generally, though, I am not a fan of people giving me their number or email. But I grew up in the Midwest, so my preferences here may not be standard. But the way I think of it is the person who makes the call is responsible for maintaining conversation and, likely, for initiating a date. So to me, it seems equivalent to someone asking me to ask them out, but in this case he'd already made the invitation, so I didn't mind a bit.

And notes, I suppose, could be pretty sixth grade. His choice of media and his little drawing, though, made it seem thoughtful and funny instead of silly.

We got married, bought the bar, and are expecting our first child in June.

Okay, that's a lie. We only went on, like, two dates about two years ago. But it was still a great pickup. In fact, I think the postcard's still in my wallet somewhere.

Good luck.

Riding the subway sounds perfect and I like the T shirt idea, maybe with read Pride and Prejudice and refer to Mr Darcy. The Twilight idea may bring on its own dangers because of the amount of under 18 reading it.

Have you tried online dating?

I am doing it at the moment and there are lots of under 40s, many more than the age group I am looking at. I hvae been writing up my experiences for the world to see.....lol.

As I'm reading through something dnelle said caught my eye:
DO NOT PUT AN AD ON CRAIGSLIST.
Mine was up less than 24 hours and I got somewhere near 200 emails... each and every one of them terrifying.

Again, I love you all!
Thanks, Stars. You KNOW I'd want your digits. That picture is so great, classic. And aren't you the looker! And you're a sweetheart.
Jay, I think the straightforward approach makes a lot of sense, thanks.
Mrs. Michaels, I always hold the door for a woman (as well as for men). My mama taught me right. Manners are very important.
Verbal, I have (successfully) done the online thing in the past, just not having any luck with it now.
Barbra Ann, I just joined okcupid, I'll see how that goes. Looks like there are some interesting people on there. I took a some dumb test about what type of sense of humor on there, and it said that I fall in the "provocateur" category. It said that my humor is very polarizing and can be too "edgy" for some. Hmm.
Luluandphoebe (and their ghostwriter), trust me, the dog thing has crossed my mind. But I don't know anyone who owns a dog. :( I live in NYC, and it's hard to have a dog here. My mom says I should get a pug when I have a situation where I can have one. I saw one today at the dog park, a stout and cute little guy with a double-curled tale.
Nice one, MissAdventures, but it would've been waayyy hotter if he had drawn big boobs (like R. Crumb-size boobs) on the girl instead of a turtleneck. Just a personal opinion.
ScienceChick, I guess that partially explains why I never get answered when I reply to ads. Because my emails are non-terrifying, my pictures are non-nude and non-traumatizing, I put time and thought into what I say....and then it probably gets lost in a sea of crappy responses. Blerg.

Maybe find out from really nice hotel Concierge, which Manhattan hot spots, especially cool restaurants with hip after work bars attached are geared to the age group you are seeking. Try the "W" Hotel in times Square or the " Millenium" Hotel in same area.

Both have great single bar/clubs inside them and there must be tons of others. Once you find one that is comfortable for you, sit at the bar and strike up a conversation with a bar tender, one that you can relate to and mention you are newly back in town and want to know a great place to take a first date to (even if that's a fib, at first), just for some information. You get the idea.

I am such a romantic from way back and I have some contacts in NYC and Long Island (not Brooklyn so much but you can get downtown pretty easily for the right situation). My 26 year old niece lives there and I will tap her for some good tips on nice singles haunts. Will also ask my 33 year old daughter who has a 24 year old friend and partner who has clients in NYC and will know some cool places.

Will get back to you with some particulars asap! No T - shirt. Don't be needy. Stay cool. When you least expect it, someone will be there and you won't hesitate to strike up a conversation and make a connection.

Starbucks or other nice coffee bars in good neighborhoods is a good option for daytime people observing, too. Ah, to be single again! No thanks!

My 2 cents worth:

Get yourself out and about. Find something to volunteer for (Planned Parenthood has a skewed ratio of men/women volunteers---in your favor!)

As for the phone number thing. Ask lots of girls! Practice! Then it wouldn't be a big deal! The more you do something, the less scary it gets! (I have to fight to not look away when a man looks at me because I'm shy--I make myself smile, because that's more inviting and it's just needs to become a habit.)

Volunteering at adopt a pet places are good too.

Well, I met my hubby on match.com in '96 we were married in '97 and adopted 2 kids from China starting in '06.

What charms me? Honesty, sincerity, creativity, and dependability and a good sense of humor. For years I attracted the cover guy types with too much arrogance and too little brains and no integrity. Match worked especially well for me because there were NO pictures in '96. I didn't have trouble attracting guys. I had trouble attracting the right type of guy, so words for me in this instance were better than pictures. Physical attraction needed to be off the table in the beginning 'cause that had always been an invitation for trouble.

one of the more successful guys i ever knew used to carry around a copy of 'the second sex'. this gets you out of the chick flick type of girl :) also, i've always appreciated a fairly confident approach which still leaves me an out, so, be charming, but not creepy.

also - and most importantly - when you get the number - don't do the damn third day call. call the next afternoon, and have a plan to suggest, fairly low key.

go forth and ....hmmm..... get numbers, i guess.

What the email-tshirt idea would say to me is "I don't care who you are really, as long as you're female"---which is probably why you aren't having much success. Why would I want to be equated with the 3.5 billion other women I share this planet with solely on the basis of our shared female-ness? What's with that anyway? What is it about me being a woman that means you get all tongue-tied and can't approach me and start up a respectful conversation? I'm a woman. I've been approached by strange men before. It's not a problem, unless---

Well, there's the sort of guy who only has eyes for the flashiest, most attractive women in the room. I don't know of any woman, pretty or plain, who doesn't find that a huge turn-off. HUGE! I'm not saying this to insult you because I don't know you from jack, but maybe you are not attracting women because you're one of those dorks?

Or maybe you're the kind of guy who goes fishing with compensatory status symbols, prestige items, and other bling which is crass and, frankly, vomit-inducing.

I'm not saying be yourself, if your self isn't attractive to women. I'm saying Be Attractive. Be loving, kind, respectful, generous, sincere, friendly, helpful, approachable, vulnerable (as opposed to needy), capable, dependable and open to women ... all kinds and shapes of women.

When you meet someone you would like to see again, ask them if they would like to meet you again. "Would you like to get together sometime?" If they say yes, then it is simple to exchange phone numbers. If not, then you know already, and can move on with no regrets.

Personally, I've always wanted a missed connection, but who doesn't. Anyway, I think being casual and funny are key.
What works on me are when a guy finds something in common to talk about. Say I'm in the book store and I'm looking at Mother Jones magazine. I think it'd be awesome for a guy to say "You know I'm really into important magazines too rather than that celebrity bullshit that everyone else reads. Blah blah blah.." Then we'd talk about cool relevant issues and then after talking for a certain amount of time (10 + minutes) of good, not awkward, conversation, we should exchange numbers. I totally just made that up in my head but thats how I would want it to go. I don't have the most experience but with my ex, we met at a protest then I asked him to dinner after running into him at Critical Mass and then we went out. I'm currently dating a guy that found me on Facebook, which seems to be normal but I'd much rather have a guy ask for my number or ask to hang out with me. It is also key to have something in common that is interesting because lately I've had a bunch of guys asking for my number that I don't really have anything in common with. I asked one on the spot if he rode a bike and it was a deal breaker when he said he didn't. Not that I don't like guys that don't ride bikes, but I was looking for something interesting about him.

S.K.Veln, did you read the whole post or any of the comments (my own included)? I am nothing like the person you describe. If you read some more, you'll see that. The idea of doing the t-shirt was a joke.
Artsfish, nice work! Did you find your kids on the internet?
Paddle, Planned Parenthood is a stroke of genius.
Rather than the Second Sex I think I may carry around an Ann Coulter book--to attract that certain kind of lady. I agree about calling the next day.
I really appreciate everyone's advice so much. :)

Chris,
I've been off the market for 25-plus years, so I can't attest for how things are done these days. But if memory serves, back when I was in your shoes, the psychological conundrum of not wanting to go to any party that would invite me was a recurring issue. We feel lonely and accept that we aren't up to par and therefor must accept any attention tossed our way on bended knee. ("Or at least get some action, ferchrissakes.") Looks like you will get some conversations started thanks to the other posters here. Once you do, enjoy them and be willing to let things go if they don't appear right. There will be others. The women I know who are your age don't like being single much more than you do. The only thing worse than being alone is being in a relationship you can't stand. Enjoy the conversations, confident that whatever is meant to be will be.

You're right, Chris. I didn't pick up the jesting tone in your final paragraph. Sorry.

Hmmm...yeah...well, um...ok...ya know...this might just be...um...the first post on OS where...um...ya know...I just...um...didn't have...well, ya know...anything...constructive to, um...add to the conversation...

You know, I would branch out of your comfort zone. Yep, that means no more lovely baristas. (No issues here, I'm a former barista that fell for a few of my customers, so...)

Take classes or volunteer. I took a welding class because I had always wanted to learn and not expecting much, made a really good friend. I also found that chemistry.com was a nice balance between eharmony.com (ugh, for another blog) and match.com (meat market). Craigslist, ummmm, only if you like the fringe.

I don't know... It seems like it's taking sooooo much longer than it used to. Just be sincere and honest, but don't rush it. Definitely, give your number - don't ask for hers. We shy violets might hide.

You'll find the one.

Chris,

The question you pose is eternal. It is a giant pain in the ass, and guys are not very bright, so we tend to just stumble into things. Without delving too deep into the specifics of Takeaway Theory, what I would suggest for you is to expand your network of female friends. Make a list of the women you like, and start hanging out with them more frequently. Meet women in non-dating situations as much as possible. The ones you enjoy, hang out with, but NEVER, EVER move on them, or develop feelings for them beyond strong friendship and loyalty. Treat them with respect, and friendship, and kindness, and they will do the rest for you.

Women are hit on in so many ridiculous ways so frequently that they are almost constantly on guard and don't really take direct offers seriously (perhaps for hookups, I'm bad at that part, but with relationships, women seem to me to be much stricter and more judgmental). This creates an interesting paradox for a man in your position, and the only proven method to success with women is to have a friend on the inside--it's a sort of Dating Nepotism. If you have female friends that you treat well (and I mean sincerely--they can smell frauds from across a bus station), they will allow you to alternately bang and date your friends, as required by Female Dating By-Laws.

Women have developed resistance to pick-up efforts as a response to being constantly approached by assholes, so they outsource the judgment to their friends. It's happening all around you, even as we speak. Once a woman knows you're legit (this might take months--sorry, friend) she will set you up with friends as they become available. Traditional dating is wrought with iniquity, but this method has remained invaluable to members of an inherently unprepared and ill-equipped gender in acquiring a female partner.

*that should say "their friends" not "your friends."

Also, you might just invent a girlfriend to tell other women about. That works too. Women love guys that already have girlfriends. Hope this helps.

I've never read any Jane Austen. Really, I have no advice for you, but I'm in the boat with you and it's a scary boat. I would say just ask. The worst thing that will happen is she'll say no.

That is not true Tyler. That's lying and it's stupid.

Chris,

I'm in a similar boat, though I'm a few years older and a remaindered man (i.e., divorced). I find things go best if I'm in an arena where I stand out, so for me classes are good. If I'm in an arena where I don't stand out, I find I attract interest if I do what I want to do instead of what I'm situationally supposed to do. In bars, I usually sit by myself, read a book I find interesting, and enjoy what I'm drinking. A number of times, I've looked up into lovely and interested faces who've asked me about what I'm reading and, after a bit of chatting, given me numbers.

Jane Austen might be OK to carry around if YOU are interested in her work. Don't carry her around just to attract women. The resulting bad karma's only going to attract bitter women who've too many cats and have pledged themselves to following "The Rules".

I wouldn't carry around "Twilight" for roughly the same reason I wouldn't carry around "Lolita". However, if you think deliberately being creepy is funny (I think it's a hoot), then make sure you moan softly to yourself while reading ... and maybe occasionally surreptitiously rub your nipples with a swatch from a blackwatch plaid skirt or something like. ;-)

The trade-off of sex for resources is the oldest game in human existence- that's why there are so many of us at present- rather than worry about them ( the females) put some resources on display- in the post - feminist world this doesnt mean cash but it can help.You need to project that youre a long term player in this game or youre dead.... emotional maturity , awareness, active listening work wonders- if this fails I suggest a Mercedes 500 SLK as a fall back position

f I may, I noticed that you said that you are capable of "striking up a conversation with women that you find attractive". Here is the hidden gem method. Go out and be yourself. Be in a peaceful frame of mind. Engage yourself in something that you like. And approach anyone on the interest, and not merely how they appear before you engage them. I am sure that you have found that a person's attractiveness changes dramatically based upon what happens once you begin to share. Observing the surface before interaction is like judging a flower before it opens to the Sun. The real character is revealed thru actions, and involvement with what the observed is interested in. Be interesting. Do the best that you can to abandon the Madison Ave. orthodoxy of appeal.

a) on the have a date not a pickup thing...will just say sometimes it's good to go around the block and do all the wrong things.

b) As a yoga teacher, I've always been surprised more men haven't caught on to the fact that classes are like 85% women, mostly women who don't smoke, are into fitness, healthy eating, and self-improvement. Did I mention flexible? I wouldn't recommend coming to class to poach on yoga students (see the YouTube video on the inappropriate yoga guy), but if you go on a regular basis and get involved in the yoga community, well, you'll have good odds of meeting a nice person.

Chris, this sounds like maybe you're still hung up on your ex and not really available. You may enjoy all the attention here cause it makes you feel better about her not choosing the relationship over the career? Irony may just be another way of staying out of the game.

I'll tell you, anyway, what works for me. Real interest from someone who has the sense to READ THE SIGNS and see that I too am interested, and attracted to them. When I show an interest, by smiling at their jokes, asking questions, and being rather sweet, THEN what works for me is BEING ASKED OUT.

It makes me feel good, just like having my coat taken, being taken care of with little things. Not cause I can't look after myself, but because basking in your attentions is my favorite foreplay.

If you wait for me to ask you out, I hope you're having fun-- you and Irony.

There are some really good suggestions here. I'll second those suggesting getting out and participating in an activity. That will put you in contact with people with similar interests and you'll have something to talk about and "break the ice".

Good luck!

The really good news - you have no problem meeting women and talking to them. That's a HUGE plus. Now...

- Be sure to talk to somebody you think you'd like to go out with, and you think would like to go our with you. In other words, it's easiest if you two are closely matched in looks / race / dress and so forth.

- Bars are good places to meet people, but better places are things like street festivals, outdoor free concerts, etc. etc. Spring and summer are obviously better times of the year.

- Volunteer to dog-sit for somebody, then take the dog to a park or one of the above-mentioned outdoor activities. A baby in a stroller is a better bet yet. Absolute chick magnets.

- Church groups for 20-somethings are sure winners. They are usually 60%+ women, and they are friendly and non-threatening. Just be sure you have a little bit of the faith to take to the group.

- Cooking classes and tap-dancing classes.

- (Never tried this, but heard it's a winner) - Saturday night AA meetings.

Chris, a lot of variables here unknown. What type of woman are you looking for? It does depend on your likes/hobbies, etc... I like reading, music, films and art. So if I were single, I'd be at bookstores, libraries, music stores, movies and art exhibits. If I see someone attractive, and looking at a beautiful painting, or a cd I like, or book, I'd mention that I really like that piece of art, book, cd. Converse. Be natural. Always be yourself. If you're not, and you do go out, she's going to discover the real you and vice-versa soon enough. Do anything you can to gain confidence in yourself. The person you know best in like is YOU. Accentuate the positives and I don't mean physically. I mean talk about things you know about but more importantly, LISTEN to what she has to say and build on that. Then when you're comfortable chatting say, "we should try this again some time", in a questioning tone. She'll give you the vibe or no vibe. If she is digging you offer a day or time. Coffee, lunch, something informal.

You can do it. Afterall, I'm married.

Chris,

I think BeesTone had good advice. Get in the habit of just talking to people. Cute ladies, hot ladies, little ladies, big ladies, all kinds. Consider it building a pipeline. Go into it with the mindset of just meeting people, not searching for a date. The more women you talk to, the better your chances. You will feel more comfortable with chatting and will likely make a few new friends and maybe meet someone that you click with. It will happen!

i really feel like i could have posted this myself, chris. i try to present myself as an open available nonjudgemental person to whatever might come my way. i don't have a problem striking up a conversation with men but damn, i'm never approached by guys. ever. i would consider myself an engaging funny attractive woman too. i get along great with new people, but only when i've put myself out there, otherwise i'll sit there silently with nobody talking all night long. but i do think there's something going on these days that makes this difficult. maybe we've just entered a certain phase in life?

i get the very rare weirdo who might like my boots or something bizarre but i have found it very difficult to casually meet new people. i say, you should definitely strike up a conversation with a girl you find interesting. and you should definitely ask for her number. or better yet, give her yours. you'd throw her off her game and you might just get that phone call. it's sweet. i often wonder why men seem to be so leery of striking up a conversation. it's bizarre and has both myself and many friends (both men and women) stymied. and the men friends have nothing to say for themselves. but you never know what people are really thinking. so, just give them the name and the phone number. see what happens.

Late to the party as usual - but... I have some friends you should meet... (I love setting people up - worked at Y! Personals for many years...) Shoot me an email if you'd like to have a drink with some smart young things.

Wear a large piece of meat around your neck.

Women love the meat.

Also, smell good.


These two things might be hard to do at the same time.

Good luck, hotstuff..



(Man Talk Now is always right about everything.)

Chris, the best advice I can think of for entangling with a woman is to get it in your own head that you don't need to. Until then, you are just sloshing with 'needy' vibes. Once you don't give a rats fanny about ever getting together with another woman in this life, you will get at least 2 and maybe 3 knocking at your door.

If you are just looking to get laid, check online. There are lots of women who have given up on the brass ring and are willing to just 'settle' ... several times a week. Try Amateur Match, Fling or any of a dozen other 'adult dating' sites. And wear a raincoat. Or two. Nothing down there that a little Lysol can't fix.

If you want a deeper attachment, just be yourself, set your compass and make progress in your life, become emotionally self-sufficient. Nothing seems to attract a woman as much as a man who doesn't need her.

From what you wrote, I got a sense that you aren't solid on what you want from / with a woman. Get that straight first.

The yoga idea, though arousing, may not work. I haven't taught yoga, I've just taken classes, but in each and every one of those classes I've thought the men in them acted like total creeps regardless of whether they were leering lecheros in the rest of their time. I would imagine it's hard to control your gaze when a number of reasonably fit people of the gender you find compelling are scantily clad and crotch-sprung within arm's reach.

Send Phoebe! STAT!!
Nada, I may be a bit hung up on my ex, but some good dating would probably put that to rest. And it's not really irony. I've always had a horrible time picking up girls, except in high school and college, where it was super-easy because of all the ready-mad social situations. And I'm really not a super-ironic person. Also, I didn't post this to get attention--the most any of my posts had gotten prior to this was like 20, and I haven't been around for awhile, so I figured maybe I'd get a couple of people to respond.
Some of you are under the impression that I'm desperate, which is half-true. It's been a long time, people. A guy wants some action eventually It's funny, but I don't see people in the same boat saying I'm desperate...I thought everyone had gone through something similar.
I think I'll skip yoga. Not only is it potentially creepy, also I am very not-flexible. Very.
Bill, I have REALLY gotten used to not needing to date or anything. As for what I want: a good, serious relationship. Barring that I'll settle for just a little action.

Internet dating absolutely works Chris . I've been doing it for a year and a half . My first rather pleasant experience was a simple post on Craigslist in the men seeking women . Posted a picture and wrote
some blah blah blah and got multiple responses and ended meeting a nice Vanessa who ended up in my hot tub after the first evening of drinks . You're right , being in a bar by yourself is at the very least AWKWARD ... and how do you know who to approach ? Just because two girls are sitting together doesn't mean there in there
man hunting . In fact more often than not it's a " girls night out "
situation and well , rejection sucks ! On the dating sites the playing field is equal and everyone is pre qualified ... all the women are single or at least interested in meeting guys . You can see there
pictures and they yours . A few message exchanges goes a long way towards knowing if you might like each other , getting a feel for a girls personality and intelligence , and she yours . You're a writer.
Use that to your advantage !
Good luck ...one that works pretty well and that is totally free is
plentyoffish.com . Post up and start relieving some of that pent up built up you know what ! And who knows maybe even fall in love
( that would be cool ) !

tp

Gosh we're as confused as you. But having read through the comments, I think I get it! If I see a guy that's cute, holding a copy of Jane Austen, it means I should knock him to the ground and start humping his leg. If he's carrying "Thus Spake Zarathustra", I should slap him in the back of the head and then say, "Oh, sorry, I shouldn't have done that. No one should do that." If he's carrying Tropic of Capricorn, I should seductively undo his belt and then start flogging him with it. If he has a copy of Teen Beat, I should stomp on his foot, and tell him that no matter what he thinks, Brad never cheated on Jen. I can't wait to get out there!
Seriously, or almost seriously... it's just logical to get on one of the dating websites - people here have mentioned a bunch - just to have the internet working for you. And the next best thing is to go see music by yourself and sit at the bar. It's an easy opening to talk to women (people!) who are enjoying the same thing you are, and have a drink in hand, when not 1) at an awkward party or 2) at a bar to which they've gone just to meet someone or just to drink. (by the way, unless my point was misunderstood, I think the idea of carrying a book around to meet women is dishonest.)

also, chris, to add to what i said above, it's also really important when you stike up a conversation to *ask* women about themselves. you'd be surprised how many people do not do that. my exhusband of all people taught me to be curious about the world and especially the people around me. until then i never realized how much i waited around for someone else to wonder what i had to offer. i guarantee you that if you seem interested in what a person is about you will get some action. and you never know what clever things might pop out of your mouth once you get the hang of it. people appreciate someone who engages them. it's really as simple and as difficult as that.

And to clover just above me here in comments I would agree
completely . People , woman especially I think like to talk
about themselves more than listen to some guy talk about his self .
I call it the ART OF CONVERSATION and even though you
might not be that interested in what they're saying , let them talk .
And when they get done eventually sat something like " Oh really ,
then what did you do " etc . Instead of trying to trump there story
with a bigger better story . So , shut up , listen , and ask questions .
Be interested , or at least ACT interested ....It'll get you miles !