Weird Picture Guy got a second date with me afterall. He texted me within 24 hours of our first date (barely scraped by) and with a little prodding on my end, ended up asking me out over the weekend. I always seem to shoot myself in the foot though. The first time we went out he offered to pick me up and I said I’d feel comfortable meeting him at the destination. This time, he didn’t offer (I assume it was because I told him it was creepy) and was disappointed.
I met him downtown mid afternoon on Saturday. The guy has no sense of style. He showed up in baggy shorts, sneakers, a sweatshirt and a baseball hat again. A little effort would have been appreciated, but not a deal breaker. We spent the afternoon walking part of the Freedom Trail, watching street performers at Feneuil Hall, eating lunch outside and people watching in the Common. It was a really nice afternoon. I was disappointed that I had booked Bradley Cooper for a date that evening, because I could have spent several more hours with him. He walked me to the parking garage where my car was parked, gave me a really sweet and affectionate hug and said bye. He texted me when I got home and said he had a nice time. He hasn’t asked me out again.
I got home in time to get more dressed up for my date with Bradley Cooper 2 hours later. He was an hour late he was coming from CT and hit Mass Pike traffic. I’ll let it pass this time, I was still getting ready, and the poor schmuck was driving 2 hours to take me out for sushi. He looked nicely dressed and met me at the car with flowers in hand when I came down. Well played. He took me to a fancy sushi place, but of course he didn’t make reservations. At this point I’m famished and drinking at the bar with him while we wait. A bad combo. Me drunk and hungry, means I am moody. He spends literally every 15 minutes throughout the night how pretty I am in one form of a compliment or another. Every girl appreciates a compliment – but it can be a bit much when it’s to that degree and it started making me feel uncomfortable. We ended up catching a movie after dinner and he drove me back really late. Before I could get out of the car he asked me on a 3rd date, at which point I felt a little overwhelmed and pressured in to this whole thing. To make things worse, when he walked me to the door, he gave me a hug and as I was pulling away asked if he could kiss me. It was awkward but I said yes. I ‘m not sure if it was because I wanted to see if there was chemistry or if I just wanted the date to end.
I feel bad for Bradley Cooper. He has everything going for him, but for some reason I didn’t enjoy myself nearly as much as the first date. Weird Picture Guy on the other hand isn’t doing much right in terms of going out of his way to impress me, but I find myself waiting by my phone to see if he’ll ask me out again. I’ll be the first to admit, woman are complicated.