If you haven't already, go read my list from 12/14/15 The Worst Date I've Ever Been on 😖 … then come back here, because tonight, 2.5 years later, I went out with her again, hoping for a different ending 👍
  1. So, I've been lonely lately. My wife and I split up over 3 and a half years ago. I'm not good at meeting girls. I met my ex-wife at work. I'm not one to go out and flirt.
    My social and generalized anxiety disorder ruin most aspects of my life.
  2. I've even signed up for dating apps, and recently, match.com
    I've been very against meeting someone online. I want it to be natural. Organic. Happen when I least expect it. Romantic. Exciting. Real.
  3. I've sent over a hundred messages. No one messaged back. It felt like 100 rejections.
    I know it's not like that, but it feels like it.
  4. So, I got lonely. I knew that Kelly would still want to hang out. Between all the jerks that she's met online and whatnot, she always enjoyed going out to dinner and chatting with me.
    Because I'm the nice guy. I'm the friend. The one someone talks to about their problems. I don't mind it one bit.
  5. She was texting me about how hard it was to find someone who just wanted to have a normal date. Hang out, grab dinner, talk.
    Mostly she just was getting tons of pictures of penises.
  6. I asked her why we didn't work out, all those years ago, after our two dates.
    I knew the answer. I wanted to see if she remembered. She didn't.
  7. So I said I'll go to dinner, talk, and hang out with you.
    She sent some emoji, maybe a blushing face 😊
  8. We decided to grab dinner. I asked if it was a date. She said we can call it a date.
    Didn't seem enthusiastic.
  9. About an hour and a half later, I kinda regretted what I had done. I thought back to our Greek festival tragedy. I panicked.
    Did I make the wrong decision?
  10. My friends all knew the story I linked to above. They told me that people chance. It's been 2.5 years since then. People grow. Mature.
    I had low expectations, but maybe they're right.
  11. Today, they told me I need to pay for her meal. I thought maybe split it. We don't even know if it's really a date or just two friends hanging out like we've done a bunch of times in the past.
    Plus, after the last date, I was hesitant.
  12. They told me to make sure I kiss her. Since we've kissed before. I told them let's wait and see what's going on.
    Because a kiss means something to me.
  13. I got to the Cheesecake Factory.
    She arrived, looking pretty.
  14. We chatted, ordered delicious bacon and cheese filled tater tots as an appetizer
    Seriously delicious.
  15. Then, as I waited for my steak Diane, she started to complain about work. I had told my friends that if she starts off complaining about work, it's going in a bad direction.
    It was all about her. But then again, who am I to stop her? She needed to vent. I'm there for her.
  16. Then, again as I had predicted, the next topic was worse. She started talking about all the different dating apps and sites she's on. Then she started reading me message she's received since this morning.
    Lots of "hey" and "what's up?" messages from these guys.
  17. Next she talks about all of her past boyfriends and why each one didn't work out. I knew most of these stories, as I'd helped her through many of the breakups.
    So … this wasn't a dare, right? Like, I'm not wrong here.
  18. Finally, after we eat some delicious cheesecake, I offer to pay. She gives me half the money. I shake it off … I should pay.
    That's what the guys told me!
  19. 85 dollars.
  20. Then, as we're sitting there, waiting for the waitress to bring my card back to sign the receipt, she brings up Disney.
    My favorite subject!! Right!!
  21. And she mentions how I should never have spent 10,000 dollars on a trip. And I should never have invited my ex-wife (aka our daughters mother). And how I need to move out of my parents house so someone would want to date me, not go to Disney.
    Soooo, first Disney conversation that I actually disliked.
  22. She went on berating me for about ten minutes, telling me that she's telling me this because she's a true friend.
    No, it's because it's none of her business how I live my life.
  23. We eventually leave. I walk her to her car. I hug her goodbye. I decided against attempting to kiss her. I really didn't want to.
    Even through the loneliness!
  24. Sooooo … yeah. I need to remember not to make stupid decisions because I'm lonely.
  25. UPDATE: I forgot to add that she told me that since I'm a Hillary supporter, I clearly want our troops overseas to all die. She said this unprompted.