I do a lot of things for my buddy with the gallery. I shred papers for him, I book bands, I make phone calls to creditors, I schedule meetings, I clean and I cook. I call him my boss, even though he's always been my friend first. He's been helping me out in my time of unemployment by giving me something to do and paying for some of my bills as a reward. I guess you could call it a job. There is only one thing I told him I wouldn't do. I would not be scheduling his dates for him. That is where I draw the line. I didn't realize how diabolical my boss is though. How calculating and plotting. Because that sucker found a loop hole. For some reason, he thought that I'd be a fantastic wingman, and he was determined to take my wingman skills out for a test drive.

Boss: Guess what time it is!

Me: Time for me to find a final band for the April 21 show?

Boss: Nope! Time to score some points with the ladies!

Me: Haha! Well, have fun with that. Where are you gonna meet ladies at this hour?

Boss: What are you talking about! It's like Prime O'Clock at the coffee shop!

Me: Seriously?

Boss: Come on. Lets go to get some coffee. I need to talk to you about some stuff that needs to be taken care of for the non-profit lawyer.

Me: Oh this is work-related? OK.

So I just thought the whole "scoring points with the ladies" thing was a joke. I thought that we were actually going to talk about the gallery's non-profit status. That's how clever he is! If he tricks me into thinking that he's joking about the whole Love Quest, he can drag me into whatever plot he's plotting and I won't have any control over the situation.

We hop in his truck and he drives us down to a little coffeeshop in Los Feliz. On the drive over, there are a few things mentioned about the gallery. We're batting around some ideas, I reiterate the challenges we're facing. It feels like a productive conversation. Upon arrival at the coffee shop, my boss buys a cup of coffee and immediately starts hitting on the prettiest girl in the place. I stare slack jawed for a second, but then I sit down on a couch with my notebook and roll my eyes. I can't escape now: he drove and all of my stuff is at his office. I just wait.

Boss: Let's go.

Me: Done? Already?

Boss: You think she was into me?

Me: Um. I guess? She seemed to be laughing at your jokes a lot.

Boss: You think she thought I was attractive?

Me: Why wouldn't she?

Boss: You think she thought I was awkward?

Me: I don't know, man! Did she give you her number?

Boss: I didn't ask.

Me: What? Why? You seemed into her.

Boss: Meh. I'm just getting warmed up. Come on. Let's go to this bookstore.

We walk to the bookstore next door and I'm getting anxious. What kind of annoying situation is he going to drag me into now? My boss buys a book. The trip to the bookstore ends without incident. But the afternoon isn't over. We still have to walk past people on the sidewalk, and 50% of those people are likely to be women, which means that the possibilities are endless.

We walk past a cafe and my boss sees a woman sitting alone with a laptop at a table. Without warning, he veers off the sidewalk and starts talking to her. He sits down at her table and I don't even know what to do. The only thing I can do is start texting people about my ridiculous situation and try not to cringe when my boss says something completely inappropriate. 

Boss:  You're here by yourself, huh?

Girl: Yep. Aren't you ignoring your friend over there?

Boss: Oh yeah. Hey, have a seat here next to me.

Me: (rolling my eyes) Thanks Buddy. 

Boss: Don't worry about my friend. She works for me.

Girl: Huh?

Boss: So. What are you into?

Girl: Excuse me?

Boss: What have you got going on there with your laptop? You writing?

Girl: Well... I was trying to get some work done.

Boss: What are you working on?

Girl: Am I a part of some kind of experiment or something?

Me: I have no idea.

Boss: We're just talkin. I mean think about it. You and I never existed to each other before this moment. And look, now we do.

Girl: Now we do...

Me: (roll my eyes)

Waitress: I'm sorry to interrupt. Would you like to order something?

Boss: I'll have a pink flamingo.

Waitress: Certainly. And you miss?

Me: Oh I'm fine.

Boss: Let me get your number.

Girl: No.

Boss: What?

Girl: I never give it out. Ever.

Boss: That has never happened to me before. Ever.

At this point, the woman sitting at the table next to us bursts out in a little giggle and hides her face. She's about as baffled as I am. I just have to wait it out. Because the waittress still has to bring that pink flamingo he ordered, he still has to pay for it, and this poor girl has to endure my boss hitting on her, and me staring at him hoping that this stupid adventure will end. 

But it doesn't. On our walk back to the car, Bossman tells me to hang a right. And I fall for it. Because guess what's just around the corner? Two chicks having lunch at a table outside of a diner. And guess what! They've got a dog! It's like someone was just setting all of this up for him and making it so easy. He sits down next to these girls, pets the dog and I have to sit at the table behind him and wait. Again, the girls mention the fact that he's ignoring me.

Boss: Oh, that's just my friend! We're having fun! Are you having fun?

Me: Can I go to the coffee shop down the street?

Girl 1: Did you just ask his permission?

Boss: She works for me.

Me: Yep. I'm gonna go.

Boss: OK. See ya. Hey, let me have one of those chicken wings.

So I go back to the coffee shop and wait for my boss to finish doing whatever the FUCK he's doing. And the cute girl is still sitting there. When he finally comes back, my boss finally grows the balls to talk to her again, and he gets her number. And I can finally get back to work. The work that doesn't involve me getting suckered into being my boss's wingman.

I know this seems horribly inappropriate, painful, and just plain annoying, but you have to understand that I wouldn't be friends with this person if he wasn't exactly the way he is. Crazy and all. Part of the adventure that is my life right now is taking care of this very frustrating person and observing how he interacts with the rest of the world. Fabulous and creative people are kind of like that in some way: frustrating, crazy, socially adventurous/retarded. They make it fun to be around them. The next time he tells me to go to coffee with him though, I just have to remember to drive myself. I'm onto his tricks now!