We’ve all had some interesting dates in our lifetime; some good, some bad. Since the online dating post, “Online Dating Terrible First Dates” more people have been open about their stories. Naturally, I asked if I could share their unfortunate events on this blog and thankfully they agreed.

Let’s check them out, shall we?


April’s Story: Sleeping Beauty

I’ve gone out with this guy a couple of times and he’s a nice guy, but I’m still just trying to figure it out. On a Saturday, I was out with some of my girlfriends and he started texting me to come see him at a place in Uptown. My friends and I didn’t have plans so we decided to go meet him and his friends.

When we got there it was completely fine and was a good time getting to know his friends. My friend was ready to head back to our apartment, but I was still fine with staying out with him and his friends for awhile. Well, this guy wanted us to go back to my place. Well that wasn’t going to happen, but I said we could go grab a drink at Cowboy Jack’s near my place.

Once we got to Cowboy Jack’s, I was starting to look forward to getting to talk with him and actually get to know him more. Then I could see if I wanted to move this forward or not. So as we sit at the table with a drink and a late dinner, I start asking him basic questions. Turns out he doesn’t really listen to music, he’s more of a talk radio kind of guy, but will listen to metal when he works out to get pumped up. Nothing wrong with that at all, but we have very different music taste. As I kept trying to hold a normal conversation, he just kept trying to kiss me or divert the conversation to something else.

After awhile of trying to hold a conversation and having it fall flat every time, I excused myself to go to the bathroom. Once I came back to the table, I find him face down sleeping on top of the table! WTH?! I leave for five minutes and I come back and he’s snoozin’. Before waking him up, I took a quick pic to document this moment in time. The date where the guy fell asleep.

I smack him on the shoulder to wake him up. He startles awake, looks at me and I told him that he fell asleep in an annoyed voice. Then how does he respond? He says, ” Well I needed a little nap.” To make matters worse, a security guard at the bar comes up to us and tells us we have to go because they caught him sleeping. Well, I’ve got to say this experience on a date was a first.

Jessie’s Story: Better as Friends

I had been away from the dating scene for awhile after my long term relationship ended, but started to feel like I wanted to see what else was out there so I downloaded Bumble. I ended up meeting this guy and we decided to meet up for the first time. Although it took quite a bit of rescheduling to actually make a date work. Finally, we met up at the Lowery.

First of all, he knows how to work the angles of a camera because he didn’t quite look the same in person as he did on his profile. More importantly, he was a little socially awkward and had me lead the whole conversation. I’m fine with leading a conversation, but come on try to ask me at least one question. I was trying to be social and just get him to talk a bit, but instead he just kind of sat there and answered me with one word answers.

Then out of nowhere…probably because I was the one just rambling on, but I say, “I just don’t think dating is my thing.” In a way that comment made him more comfortable, or something, because then the conversation moved to how we would be friends. He even said, “Yeah we can just have this be a one and done.” We had a lovely dinner and it felt very freeing to be honest with each other about our feelings.

We went back to my place after dinner so he could drop me off and we hugged good night. I even gave him one of those pats on the back you do to your cousin or maybe a neighbor. Once I got inside my door I got a text from him saying that he had such a great time and couldn’t wait to see me again. Staring at the phone with a twisted face of confusion, “I thought this was a one and done?”

Mandy’s Story:  Staring Contest

A couple of years ago, my best friend wanted to set me up with this guy. She told me that she thought I’d like him because he’s cute and we had a lot in common. So of course, I agreed to meet up with him.

I get to Barrio in Edina, sit down for dinner and realize fairly quickly that we do NOT have anything in common. Sure, my friend was right about him being cute, but was so incredibly wrong about our compatibility. Anyway, that’s not even the worst of it. The most odd part of the date was how he never stopped staring at me! Not in the cute way either. The kind of staring where he never broke eye contact; even as he took a bite of his food. I didn’t really know what to do with myself as he kept staring. These situations make me want to make a quick get away, but I couldn’t because he would see it!

Finally, the date was coming to a close and he asked me what I was doing for the rest of the night. I panicked and responded, “I’m watching a movie with my mom.” Just as I heard the words come out of my mouth, I thought to myself “WHAT?! That’s what you came up with?” Well, I was not going to watch a movie with my mom, but didn’t know what else to say to make him realize that I was busy. Maybe I should have said something to make him think I was more cool, but that sure didn’t happen. I’ve never been too great at thinking quickly on my feet. Either way, between the non-compatibility, awkward staring and my lame excuses we didn’t plan a second date.

Your Turn!

Do you have a bad date story? If so, submit it in the Contact Me box to get featured!


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