Worst First Date(s)

First dates are the worst. They’re awkward and anxiety-inducing. But (almost) every great love story starts with a first date. Then again, so does (almost) every awful and disastrous heartbreak story. Despite this—we go on first dates in hopes that they lead to a second date, which leads to a third, which leads to that cliché “I’m marrying my best friend…” moment or somewhere in that happy-ever-after-ish ball park.

As we get ready for that first date we get nervited, (nervous-excited) wondering if our date will like us or if we’ll like our date. Will our date be a total sociopath like last time? Or will they be so normal it’s watching-grass-grow level boring? We contemplate what shirt will let our date know we are funny, smart, kind, caring, and extremely skilled in bed. Does the purple checkered shirt say “Hello date, welcome to the first day of the rest of your magical life?” or does it say “I snore when I sleep and am intolerable before coffee…and sometimes even after coffee.”

My worst dates have never been the first ones. I’ve had plenty of weird and awful first dates. I’ve become a personal chauffer for a date, helping her drop off her car at a scheduled appointment at auto shop (that means she planned on having me drive her there after our date the entire time) and then driving her to a friend’s house. I’ve sat in silence with a date because neither one of us could find anything to talk about (she actually wanted to see me again.) My worst first date was just uncomfortably awkward and unnecessarily long. It should have ended before it even began. I was walking down the street toward the restaurant when I saw a woman, who looked an awfully like the date I was supposed to be meeting, walking towards me. Which meant she was walking away from the restaurant, in a hurry. “Hey, Morgan!?” I said, probably a little louder than was necessary, since at this point she was a foot in front of me. She looked up, surprised to see me. “Uhh, oh, hey Jay. I was uhh well I just have to run to go get something real quick. I will be right back.” We smiled forced smiles at each other.

I walked into the restaurant, wondering if she really would return. I’m pretty sure she had changed her mind and was trying to escape the date and I just foiled her plans. She did return. There as a loud band playing and the restaurant was super crowded. We were seated in a corner behind the bar, meaning most of the night there were people standing far too close to us. Within the first 5 minutes I think we both knew this was not going to become a second date. But it would have been rude to say that, so we carried on. Dinner became dessert and dessert became a walk. Neither one of us knowing how to pull the plug. Finally, I asked if she needed a ride home, she nodded. We drove in silence, politely said good night and our story faded to black.

That’s my worst first date. I asked some friends for their worst first dates…and wow. They all need to be guest bloggers because suddenly I feel like I’m a dating expert! Here are some of the most cringe-worthy. Remember, these are not my experiences. These are real life other people’s experiences.

1a. I think I’ll go with the time a guy stole $40 from me. Like, walked off with my money and was like, “I’ll be right back…” and I’m still waiting. He also didn’t have any teeth- which I failed to notice on the online dating profile.

1b. Or there was the time wherein, after we bowled, played arcade games, and ate pizza- I was informed he was married and his wife had been waiting outside in the car for him the WHOLE (like a good two hours) time!

  1. Guy told me he worked as a “caretaker”. I assumed this meant as an in home aide or something. It turned out that meant he grew marijuana.
  2. A woman invited me to attend a church where she was singing in the choir and said we could hang out after. Instead, after she needed to stay for a meeting so she could get a job in that choir, so I ended up going to lunch with her parents, and she stopped by at the end to say hello. We ended up dating for a bit, and there is a much longer version of the story I refer to as “my worst first date, that lasted six weeks.”
  3. A guy tried to show me how open he was to my culture by taking me to the museum of African American history. Needless to say the walk through the slave ship killed my mood. He also slipped in the museum and took me down with him which gave me great insight to our future. When we got back to the car he realized he locked his keys inside.
  4. A guy tried to convince me that he invented the grilled cheese sandwich. Like, he was 100% sure it was his idea.
  5. We decided to go see a movie, and while we were waiting for it to start he proceeded to describe the giant scoreboard that God and the devil use to keep track of who has “won more souls.” He then proceeded to tell me that if I didn’t accept JC as my personal Lord and savior I’d burn in hell for eternity. I guess that speech exhausted him, he fell asleep during the movie, snoring at full volume. When he dropped me off after the date, I told him thank you but I didn’t plan to see him again he asked me repeatedly if he could at least get a kiss…
  6.  Date started off with the guy getting mad at me for not letting him open my car door for me. Top that off with numerous “Women shouldn’t do this or that” comments during dinner, and I could safely say it wasn’t going to work out.
  7. I went on a date with a woman who happened to be a psychiatrist. It was impossible for her to have a conversation with me, she just kept asking things like “how did that make you feel?” If she had my address she probably would’ve mailed me a bill.

I don’t know about you, but I feel much better about my dating life after reading these. I’ve had some terrible dating experiences and I’m quite the awkward dater. But it’s safe to say these are lines I have not crossed. Next time I find myself feeling insecure about my dating abilities, I am going to remind myself that I’ve never done any of the above offenses. These stories certainly decrease my hope for humanity, but my personal confidence has increased dramatically.

Do you have a horrible first date story? Share in the comments!

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2 thoughts on “Worst First Date(s)

  1. A first date I had a few years ago began with an invitation to stop over at her place one night for a sleep over after I had gone out with some friends. We had talked for quite some time online and I guess she was comfortable in asking me to sleep over. Anyways, we talked for a while, watched a movie, and then went to bed together. Nothing X rated, a little kissing. I slept well and she even made me breakfast in the morning. I changed clothes and she walks me out to my car to say goodbye. We discover that my car had been towed. She had me park in a tenant parking space. We go back inside so she can call to find out what happened. She proceeds to full on yell at her apartment’s office staff. Like crazy person yelling. We call the tow company and she does the same thing. She drives me to the tow company office and yells at them in person! I pay and we go to the lot where my car is. Again, she goes off on the driver. I had over my receipt and get my car back. She then decides to be sweet again, hugs me, and says she had a nice night and wants to see me again. I was speechless and just said I would talk to her later.

    I texted her and said that I had a nice night, but the morning gave me serious reservations about more dates with her because of her anger. She said sorry and that she would make it up to me, but I declined and basically said good luck.

    Most expensive first date I have ever been on.


  2. Better than being stood up for date with no contact or apology just a bullshit excuse the next day. ✅


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