In honor of Valentine's Day season, I'm posting some of my favorite tales of chocolate-covered-absurdity from the single days. Enjoy!

Sarah doesn't typically gush. So I was intrigued when she called and asked in a voice that fluttered with high-school dreaminess if I’d met Milt at her neighborhood yard sale last weekend.

I hadn’t met anyone at that yard sale. But, apparently, Milt had noticed me spacing out in my lawn chair, bathed in Philadelphia humidity in my faded black tank top. Apparently, Milt liked what he saw. And I tried to recognize my typically underwhelmed friend as she chattered excitedly about Milt. Milt! He’s so handsome! He’s such a great guy! Milt is very single and very particular about women, but Milt noticed you at the yard sale and wants to meet you! 

She also mentioned that Milt was in his 40’s. But that wasn’t much of a concern. I’d dated older men before. They were sweet and, well, let’s just say...housebroken. They’d make actual dates instead of meeting up at Dirty Frank’s. They weren’t allergic to returning phone calls. If you were carrying something heavy, they’d offer to help you with it, or at least hold a door open for you.

But there was another element, too. Something a little more base.

Men find young women desirable for all the obvious sexist reasons. I’ll admit, I found it downright intoxicating to be the recipient of that desire. Guys your age can take or leave you. There are dozens more just like you in any bar on any given night. But being with an older guy changes the playing field dramatically. Suddenly, you’re fascinating just for showing up. Suddenly you’re the closest thing to Scarlett Johansson this guy’s got a real shot at. Yes, you’re the object of some dude’s sexist drooling gaze. But if the guy is attractive, smart, and fun; if he’s savvy enough to parlay the drool into charm and skillful seduction...well, it can be delicious under the right circumstances. That’s all.

So anyway, I tucked Milt hopefully away in the back of my mind and went about my day. After some phone tag and consulting our calendars, Sarah and I finally found a date that would work for all of us. It also happened to be Milt’s birthday. He and a few friends would be celebrating in a trendy diner. Perfect! We could meet in a social setting, with Sarah there and no awkward blind-date vibe.

I was so excited about my upcoming date that I let it slip to a recently-engaged friend. Let's just say she didn't share my enthusiasm. A guy in his 40’s? Why was he still single? Where was this going?

I suppose those were fair questions, though not much of a priority for me at the time. But maybe my friend was wrong. Maybe old Milt was getting a little weary of playing the field. Maybe our passionate fling would give way to sweet domesticity. Stranger things have happened.

Our big night finally came. I put on my too-short dress and a fuzzy black sweater and took a hopeful cab ride up to the diner. I nearly tripped up the stairs on my own giddy anticipation. I saw a few people sitting in a booth. There was Sarah and her boyfriend. And there was...Milt.

Or was it the hippie dad from “Dharma and Greg”?

I smiled to cover my initial disappointment and sat down across from him, studying his face to see what Sarah had found so attractive. Bald, except for a fringe of salty-peppery hair that fell just a little too long. Sweet cow eyes under a dark pair of eyebrows. A long, kind face. I never got what people find so attractive about cheek bones, but the guy did have a decent set of cheek bones. Maybe that was it. Or maybe she simply remembered an earlier version of Milt. They’d known each other for years, after all.

I chatted and nodded and looked at him this way and that, catching his glimmers of attractiveness, trying to match the person in front of me with the fantasy I’d been nursing. He was funny and interesting enough. There could still be something here.

And then, more guests arrived: A pack of girls about my age. Maybe younger. And definitely more gorgeous. They were like Shirley-Manson-of-Garbage’s sorority: dyed red bobs and dark lipstick, wildly stylish and bubbling with the energy of girlfriends who’ve just shared a cab ride.

Milt! Milt! They poured into the booth behind him and lavished him with hugs and flirtatious greetings. They had a present for him: a Spam snow globe! (Milt apparently loved snow globes, a detail that made me belatedly and unrequitedly attracted to him. He loved kitschy irony too! Oh Milt. We could have had such a damned good time together.)

 
As we settled into the new, more raucous vibe in the diner, I settled into benign but certain disappointment. Milt and I made a few more attempts at small talk, but before long we mutually, wordlessly agreed to go our separate ways for the evening. Sarah and I caught up on gossip from our old workplace. Milt cavorted with his harem. I stayed for a polite amount of time and caught a ride back to my apartment. Que será.

I was too embarrassed to ask Sarah what the deal was with the hot chicks, and she was probably too embarrassed to mention it. But I’ve wondered about it many times since then. If plain-old-me wasn’t attracted to Milt, what did these alternababes see in him?

When I told Mr. Black this story years later, his first guess was that Milt must be rich. But that wasn’t it. Milt's job wasn’t much more impressive than mine at the time. His next guess was that Milt must have been their drug dealer. Possibly. But I doubt it.

No, I suspect their attraction to Milt was no different than my interest in older guys in general. Drooling or not, sexist or not, that adoring gaze from the right guy can be one of the most affirming mirrors you could ever have (particularly if you’re Shirley-Manson-hot, I’d imagine). And in a single-girl life full of absurdity and rejection...well...sometimes a jolt of male-gaze-fueled self-esteem is all you need to make it to the next adventure. Sometimes.

A version of this post originally appeared on my personal blog: http://www.floorpie05.blogspot.com/