The Mark(us) of a True Wingman

It's been an ongoing joke on this blog (and my actual life) that Leo is the worst friend to have with you when you're single and looking for female companionship.

I've discussed it before: he's the worst wingman ever.

It's not intentional. Leo has actually been known to say to me (verbatim), "Let's get you out of that condo and into vagina." He always wants to help me out. But it's a problem when you're a hot piece of eye candy for girls. It's not his fault.

* * *

I haven't seen my old roommate since he moved home to save up for our European adventure, so needless to say I was excited to reunite with him for a night of boozing... just like old times. Leo met up with me and a group of our high school friends at The Blue Moon bar in Portland. He walked in the door in a long, black pea coat and Chuck Taylors. He gave me a hug and offered to buy my first drink.

Monica, a friend of a friend not known for her use of subtle hints, shot me a look as soon as she took notice of Leo. She quickly beckoned to me when Leo was occupied elsewhere and I approached her.

So@24: What's up?
Monica: Um. Your friend over there is fucking hot.
So@24: So what... you want me to put in a good word for you?
Monica: God yes.

I know Leo doesn't ever need it, but I always like to feel like I'm helping out when the opportunity arises.

So@24: Hey, my friend over there thinks you're cute.
Leo: Who? That girl?

-stared ahead-
-slurped beer-
So@24: Yeeeeeup.
Leo: Oh. Cool.

Leo clearly wasn't interested. Another one bit the dust.

Moments later, Nancy walked into the bar. Nancy was a coworker of mine when I worked at my very first job in high school. It had been years since I've last seen or even had contact with her, but through the magic of Facebook... these things tend to be possible.

She had texted me and wanted to meet up, so I told her I was at the bar with friends.

Nancy and I weren't extremely close when we worked together at the movie theater, but I do remember sharing good conversations with her while we slaved together cleaning out the greasy popcorn popper.

She was much more attractive than I remembered her; I guess people tend to grow up and change physically from high school to post college, eh? Or maybe she looked better when she wasn't wearing that beloved movie theater uniform: the vest. In any case, she had a pretty smile, ample bosom, and cute freckles. Nancy had grown up.

Nancy gave me a hug and I bought us a round of shots to start the night off. It was fun catching up with her and reminiscing over our movie theater days. I was starting to feel pretty confident about the situation. We were both drinking (heavily) and the conversation never had an awkward moment.

At some point in the night, Leo took notice of this and pulled me aside.

Leo: So what's going on? Think something might happen with you and Nancy?
So@24: I dunno... maybe?
Leo: I think you're doing alright. Remember: cool as a cucumber, baby. Cool as a cucumber.

The rest of the evening was relatively uneventful. I mingled with old friends, bought rounds of shots, introduced Nancy to a few choice members of the old gang, etc.

However, as fun and light as my exchange with Nancy was all evening... my Spidey Sense was tingling and not in the good way. I think this sixth sense develops when you're single. If you have to question whether or not the girl is interested: she's probably not. I had a feeling Nancy's interest were elsewhere...

Nancy: So your friend Leo is pretty cute.
So@24: Ahhhh... yeah, he gets that a lot. He's a good guy.
Nancy: What do you think?? Should I go talk to him?
So@24: Sure, go for broke.
Nancy: I just ordered you and I drinks, I'll be right back!

Leo was at a different part of the bar, catching up with our friend Markus. Nancy jumped out of her bar stool and bounced in his direction. I wasn't too upset, this was a situation I've run into before. I raised my whiskey and coke and downed it in just a few gulps.

Moments later, Leo tapped me on the shoulder.

Leo: How's it going with Nancy?
So@24: She's not into me!
Leo: Really? I thought things were going pretty well.
So@24: She's into you, you bastard.
Leo: Oh fuck that.
So@24: Eh. It's not a big deal.

Leo left to rejoin our friend Markus. I turned back to my conversation with my cousin Mimi and other friends.

I felt another tap on my shoulder again. It was Leo.

Leo: I just kissed Markus.
So@24: ... ... what?
Leo: I told Nancy that Markus and I were a couple.
So@24: You told Nancy you were gay??
Leo: Hahaha! Yeah! She didn't believe me and called me out, so I grabbed Markus and gave him a big long kiss.

I choked on my drink and busted up laughing.

So@24: Wow. Just. Wow. You really didn't need to do that, man. I wasn't that into her.
Leo: Eh fuck it. It was pretty funny. You should have seen the look on her face. Fucking priceless.
So@24: A for Effort, but I don't think I'm down with being "default". I still got your next drink though, you fucking weirdo.

Leo threw an arm around me and lead me back to the bar.

Leo: Besides, she wasn't that cool anyway. We still got New Years to look forward to.


I've heard of friends talking up their buddy to girls. I've heard of friends taking home "the ugly girl" in order to help out their friend in need.

But I've never, ever heard of a friend kissing another guy as a means of helping his buddy get the girl.

Maybe Leo is a better wingman than I thought.