And then there was the time that I threw my underpants at a stranger.

So this weekend a friend of mine was all like “Your whole blog title is about underpants. You have to blog about this.”  And by “this,” she meant the time that I threw my underpants at a stranger while I was talking to him about a date I accidentally asked him out on while thinking I was setting him up with a friend.

Jealous of my life yet?

I suppose we should start at the beginning. You see, several months ago I was chatting with a guy who always goes to the gym at the same time as I do. Every day, almost without fail, I’d see this guy for what must’ve been at least a year. I also kept seeing him on my train to and from work, so obviously we had a ton in common. Anyway, I eventually decided that it was weird not to acknowledge each other and I struck up a conversation while on the treadmill one day. Which is a perfectly normal place to start a conversation if you want someone to never, ever speak to you again.

Fast forward to: 3 weeks later when I decided that I should introduce said Gym Guy to a lovely friend of mine who I thought might find him at least mildly charming for a few hours. I’m not one of those really super-awesome friends who sets you up on a blind date to ensure that you hate me forever. Instead, I decided it’d be perfect if I could invite Gym Guy out with some of my friends who were all meeting up at a bar nearby that coming weekend so that my friend could have a neutral, pressure-free zone to scope him out and see how it felt.

I mean, how could that go wrong?

The problem with life when you’re me is that I have an uncanny ability to completely screw something up that is incredibly, awfully simple. It’s also a muscle I like to exercise on a near-weekly basis.

Me: “Hey, you doing anything fun this weekend?”

Gym Guy: “No, not really. What about you?”

Me: “I’m actually going to this bar pretty close by with some friends. If you’re around, you should come by!”

Gym Guy: “That sounds great! I’d love to.”

Me: Walk away without giving him any information on the date I just invited him to.

Also, that night when I went home and told CB about it, this happened:

CB: “So you definitely asked that guy out on a date today, fyi. I bet it’ll be a pretty big shock when he meets me.”

Me: “What?! No I didn’t, I want him to meet _____________(fill in name of fun friend here)!”

CB: “Yeah, but he doesn’t know that.”

Me: “Crap. But no problem, I can fix this.”

CB: “I can already tell that this isn’t going to end well, so whatever you do, just please leave me out of it.”

And then I gave him this face.

In a shocking turn of events, it went downhill from there.

So after I’d accidentally stood Gym Guy up on the casual date I asked him out on, forgot to mention my boyfriend or the friend I’d like to set him up with, and then acted totally like it didn’t happen every time I talked to him after asking, Gym Guy finally decided to address the situation.  Also, this is another great trait of mine: pretending something awkward didn’t happen. But it’s only great if you’re me and not someone with normal social skills. The problem here, though, is that when he decided to be socially appropriate, I was busy spazzing out about possibly losing my work ID and was frantically digging through my gym bag while he was talking to me.

And then, in a slow motion montage that is usually reserved for the movies, I found my ID and whipped it out of my bag as he was talking to me about maybe setting up another time to get together………

..….and then my sweaty underpants fell at his feet.

Right? I know.

You might wonder how this could happen, but it’s first really important to mention that it sometimes gives people a headache when they enter too much logic or thinking into how my life unfolds. However, I’ve included a picture for your reference so you can see how underpants could totally get caught on the little loopy thing! See? It’s totally not my fault!

Oh, and then it got a little bit weird because Gym Guy leaned over to pick them up as I panic-sweated and said nothing. But as he got closer he said, “Oh, uh…I should probably let you get those." And then I picked them up without saying anything, shoved them into my bag, and walked away.

What?

Yep, I literally just walked away. You see, if you walk away and you don’t see his horror-stricken face anymore, it didn’t happen. It’s like magic.

Oh, also, if you guys have any good leads on a gym in SoHo, please email me.

See, I told you that this blog would provide hours of stories about my underpants! You're welcome, blogesphere, you're welcome.