ever cry on a first date?

I did. Here’s that story:

Bill (name changed) is a really good looking, well-dressed man. He works in telecommunications, travels a bit for work, is from Louisiana and makes homemade Gumbo – yum! I also saw him on all three apps – Happn (definitely sent a heart), Tinder (swiped right), and then OkCupid (well, he’s definitely single and looking). He first sent me a message on Tinder that was suuupperrrr generic, something along the lines of “hello, you’re pretty. what are you looking for this evening?” I responded with, “generic message much?” Brat. He then said no, he really typed it specifically for me. Hmm..I’m not sure if I believed him but it was sure nice to think about. Small talk ensued for a bit more that night and that was the end.

When I saw him on OkC, I decided ok I still think he’s super hot and it was time to message him. I said “you are seriously on every app, huh?” Brat, I know. He said “No, are you?” I told him that OkC was the third app I’ve seen him on and he said that they weren’t working? Then, this happened:
Me: What do you mean? Are you asking people out?
Him: No. Not at all. Doesn’t ever seem to get there. (uhhh…what?)
Me: Aw why don’t you just ask! Would you like to get a drink sometime?
Him: Yes for sure. I’ll be back Thursday night or Friday.
Me: I wont be free until Monday or Tuesday. Does that work?
Him: Yes. Monday works!

Alright, homegirl has a date! We chatted more and I learned about what he does, where he’s from and all of that. He has his shit together, something I definitely appreciate. Did I mention that I think he’s hot. I love a boy that can dress well.

Since I asked him out on a Tuesday, we had a lot of time to chat before our actual date. He kept asking me to hang out prior to and I couldn’t due to prior obligations. Is he over-zealous or just horny? On Sunday, my type-A personality kicked in and I wanted to know what the plan was. Since I asked, I figured that it was my responsibility to figure out the date/plan. His response: yeah let’s figure something out. Then didn’t hear from him for the rest of the night….well okkk then. On Monday, actual date day. We chatted for a bit then I finally said, hey what do you want to do tonight? He said, something physical (tongue emoji, winky emoji, smiley emoji). Yup, definitely NOT having sex. So I said, bowling is physical – want to do that? He was a little skeptical at first but agreed and suggested we get pizza and then ice cream. Cute! Since I had just moved into a new apartment over the weekend, I needed to get some maintenance taken care of after work before the date. I told Bill to meet me at the bowling alley at 7:30pm. Around 7pm, I get three text messages within seven minutes from him asking about the maintenance work and then the last message.. “Are you standing me up?”  ….wtheck?

I texted back and said no, I’m leaving in 10 minutes. I was busy getting ready. Then he said he hadn’t left yet……

He pushed our date to 8.

When we finally met, man he has a pretty face and is a little shorty pie. He is also really soft spoken..I didn’t know if he was nervous or if he is really quiet but I don’t like that. I would imagine someone in sales would have a bit more confidence. Anyway, we ended up getting a pitcher of beer and ordering pizza. We only got through 1.5 games of bowling because we kept chatting which was a weird catch-22 for me because I like to play games and really wanted to bowl but I also wanted to listen and talk with him. We only had an hour to play! I ended up a littleeeee drunk before the pizza came because I hadn’t eaten anything since noon. Oopsies!

Then after bowling, we got booted out of the alley because they were closing and he drove us back to Wicker Park to go dancing. Duly noted: nothing is really happening on Monday nights in Wicker. We got into cover shows for free, Double Door closes early, Debonair Social Club isn’t open and Crocodile plays house music to a group of 5 people. We had a drink at Crocodile then walked across the street to another bar. Yup, I was pretty drunk now.

Because I have no filter when I drink, I asked him why he is super quiet. He used to have tubes in his ears which caused him to be on the quieter side. Alrighty. We started talking more about our families and where we came from. His dad had passed away and was into drugs, which is an unfortunate situation. Then I started talking about my dad. Back story:  Without going into too much detail, my dad and I had a major falling out when I was 10 and we didn’t talk until I was 20-21. Yes, this situation had a major emotional impact on me but I use it to my advantage to help others in similar situations and to become independently stronger. He then said “well, isn’t it your fault that you two stopped talking. You shouldn’t stop talking to your dad.” That was the it, and of course being under the influence didn’t help. Cue tears and me getting upset because he didn’t listen to my entire story, he just interrupted me AND made assumptions based on his experience. He did not ask questions or even hear that my dad and I now talk..caaamoonnn. As I was wiping away my welled up tears, he explained himself and said he didn’t say what he wanted to say correctly. Fine.

Then, I got up and kissed him. Not so good. It was a little hard, and a little messy. It progressively got better and then I said I wanted to go home because I was tired. He dropped me off and kissed me good-bye.

Here’s what really sucks – he is an amazing guy sans the soft-spokenness, and I’m not excited about him. When I got to my apartment, I picked up my phone and called Chuck. Of course he didn’t answer, but texted me an hour later and said he was in Florida…I didn’t respond. I don’t know why I can’t get over this kid…oof.

—

I talked to my new (and awesome) roommate and he said that I should just have fun with Tinder and swipe right to everyone. That will increase my probability of meeting someone awesome because if you say yes to everyone, then you can effectively weed out from more prospects and have fun. It’s been 12 hours since I started and it is significantly changing the Tinder game. I imagine I will have lots more stories to come 🙂

xo.