J.R., Chicago

This wholesome boy-next-door story starts right where it should, in a dark bar in Chicago.

I was out with some girlfriends visiting from out of town, we had each drunk our body weight in vodka, and we started talking to these guys. There was one who was tall, cute, and funny as hell- we'll call him "Big E".

When I decided to leave, "Big E" offered to split a cab to make sure I got home. Figuring it was a ploy but down to make out anyway, I said sure. When we got to my place, "Big E" doesn't get out of the cab or try to make a move- instead asks me if I'd go to lunch with him the next day. I was annoyed he didn't want to make out and I figured it was a blow-off, so I gave him my number & said whatever.

Alas, the next day, he calls and asks if I'm still in for lunch. It was a gorgeous day, I was starving, and I still had all of my makeup on from the night before (don't judge me- and for the record, it still looked pretty good!) so I said why not.

"Big E" picks me up in some sort of death trap, still in his clothes from the night before. He is wearing flip flops and starts scratching his foot vigorously- which is problematic, since I hate other people's feet. Even more so when they apparently have a fungus. Then as "Big E" is driving & I'm checking him out to see how thick the vodka goggles had been the night before, I realize... he has braces! Not invisalign, old school metal mouth. Wow. Didn't see that coming at all.

At this point, I'm locked in for a meal, so try to make the most of it. I make small talk, asking what he does for a living. Response: Union Pipe Fitter. ?? I don't even know what that means, but I don't have much time to ponder as he follows with the doozy that he is only doing that until he breaks through on the competitive BMX racing circuit. Dear god.

Now I feel like we've been in the car for an hour, so I ask where we're going for lunch. He mentions he has to drive to Andersonville (about 20+ mins) to drop something off for a friend, and asks if I mind. Mind? We've already been in the car for 15 minutes, so I agree. Then he goes on to say that his friend is a huge pothead and we're returning the bowl she left in his car. Perfect.

After the drop-off, "Big E" promptly finds the cheapest looking place around since he's in the mood for a burger. As we sit across from each other, I'm lulled into a trance by the flashing metal until I hear him say, "Look- I'm not trying to brag or anything, but I have a really big dick." I ask him to repeat himself, b/c I'm sure no guy would say this on a first date and I must have misunderstood. I didn't. I have no idea why this is relevant before we've even kissed, or gotten our coffee/water/coke, for that matter. But it's important b/c he's telling me a story about messing around with a virgin who was hot & cold, and that ultimately it couldn't happen b/c of... um... fit issues. Excellent brunch conversation, where's my grandma when I need her?

Oh, she would have loved the part when he mentioned trying to roofie me so we could mess around after lunch. Clearly I'm dying to get out of there, but on our way home - just to make one final impression - "Big E" decides to do his post-meal oral hygiene routine in the car, right next to me. I don't know what all happened, I squeezed my eyes shut, closed my mouth & turned my head away until he was done. Guess he was hoping to make out when he dropped me off, which I shut down pretty quickly. Didn't stop him from trying - awkwardly, in front of my neighbors who were sitting on our shared stairs - but I finally got him off my sidewalk. Didn't stop getting text messages for about a month, though.