So, this past Saturday (Halloween), I (24M) asked one of the college waitresses for their numbers when she brought the check.

A close friend of mine and I went to said diner as most of the other places were closed and it was fairly cheap, so being college students ourselves, it was where we stopped for a bite. Now, the waitress who took our orders was cute, and in between conversations on politics and philosophy (yes, that's what we actually talk about in our free time), I kept glancing over at the waitress. My friend noticed and asked me what I was looking at. I admitted I was looking at the waitress and said that I thought she was cute. Now, I'm very much introverted and don't have a lot of self confidence, so I initially didn't plan on asking for her number, but I ended up telling him that that was exactly what I was going to do. My original plan was the next time she came over to ask if everything was alright, I would check my phone and say, "Yes, I can't seem to find your number anywhere in my contacts". However, my phone died earlier in the day and was back at my apartment, charging.

So, not wanting to waste the opportunity, I waited until the check arrived and when she handed it to me, I looked at it for a moment, acting as if I was looking for something that was missing. She noticed and asked the question I wanted her to ask and while I did stutter a little at the beginning, I powered through. I said, "Yes, I can't seem to find your number on here." She smiled and laughed a little, saying she hadn't heard that one before. She went back to serving as there were other orders that needed to be served but I noticed that she would occasionally glance in my direction while she was doing so. I think I got a small win on this one and plan to go back this Saturday as well, partially because the food is kinda good and I get payed on Thursday, but also to try again. I also think the fact that I was dressed like Jude Law's Dr. Watson plus period glasses helped.