28 More of my Worst Dating Moments

Right before my 26th birthday, I came out with a list of my most memorable and terrible dating moments. It went “viral,” at least, in my world. I STILL have people bring up this post at parties and gatherings, which usually ends up with people huddled around a phone, laughing at my misery. If you missed that post, stop and read it here.

I have had many more crazy moments, some I didn’t share in the last one and several more that I experienced in the short 6 months between that post and falling in love. One of the things I most enjoyed since my last post is how many women have opened up to me, confessing their own tales of horror.

As I said in my last post, opening up about these moments takes some vulnerability–even though I was intentional and careful about dating, I still found myself dealing with creeps. Unfortunately, we live in a culture where our first thought is “How’d you find yourself in this situation?” and end up blaming the woman. That said–don’t judge, just enjoy:

  1. The guy who, when I asked what his favorite genre of movies is, he responded with, “Well, I really liked Mall Cop 1, but I hated the sequel.”
  2. The guy who broke up with me through text saying, “You’re a Proverbs 31 woman, and I would have loved that in college, but you’re too good for me today.” He didn’t get far enough with me to have known that I resent that passage.
  3. The guy who texted me every day for two months after I broke things off with him, each time saying “you’re pretty and I miss you.” You’re desperate and I’m blocking you.
  4. The guy who messaged me 6 months after breaking up with “How’s your bod?”
  5. The guy who randomly messaged me a year after we dated with “Sometimes you just need to make out with a pastor and get some holy kissin’ in.”
  6. The guy who I met online, and we quickly established that he was another local UMC youth director. Five minutes into chatting he asks me if I want to “come over and snuggle.” Lawd.
  7. The guy who, after several months of flirting online, we finally go on a date. Afterwards he texts me, “are you okay with having sex before marriage?” The guy was the worship pastor at his church.
  8. The guy who ghosted me (I was okay with it, to be honest), but several months later texts me to check in with me because he still thinks I’m a decent person. He said that he ghosted me because he “just can’t have sex with a youth pastor.” As if there was an offer?
  9. The guy who, after a month of dating and after a really great date, immediately texted me: “I think things are going really great with you, and I can see this going somewhere. First you just need to accept my devout atheism.” …how is this the first time this came up? (okay, enough with text tragedies)
  10. The guy who moved here from California a week before our first date. I asked him why he moved and he said that he felt like God told him to, and he didn’t know why yet. After Facebook stalking him, he moved to Indiana because God told him he was going to find a wife. And he told all his family and friends that. In a public Facebook post.
  11. The guy who knew I was cooking dinner for him for the first time, and then showed up three hours late. It was my first time ever cooking for a man. Ever. But I pressed on.
  12. Another guy who, on the first time I cooked him dinner, I asked if he had any allergies. He said none, but apparently he was severely lactose intolerant. He spent 20 minutes in my bathroom after dinner.
  13. The guy who I didn’t realize was ghosting me; I thought he was just wrapped up in finals week in his last semester of grad school. Being the wonderful woman I am, I made him a finals week care package and left it on his front porch. I didn’t hear from him again.
  14. The guy who wouldn’t let me eat any of the nacho cheese from our pretzel app on the first date. I made a joke about how people in Indiana like to dip everything in nacho cheese, so he told me I couldn’t have any. I sat there and choked down a dry pretzel…and tears. I love cheese.
  15. The guy who thought it was appropriate to put his hand in my bra on the first date. Before you judge me–he was too slick. Obviously he had some practice.
  16. The first time I went over to a guy’s house, he had me drive around the neighborhood for thirty minutes because his mom had decided to pop in.
  17. The guy who gifted me a copy of “The Mist” on our third date because I said I liked scary movies.
  18. The guy who texted me all day before our first date, asking me what he should wear and what I would want to order when I got there.
  19. The guy who couldn’t stop staring down my dress on our first date as I was talking.
  20. The guy who, on our first get-to-know-you date, kisses me on the couch of my favorite coffee shop. And when I laugh and pull away, he kisses me again. Don’t ruin coffee for me, dude.
  21. The guy whose apartment had no furniture but a futon and a card table, with mallard wallpaper on the walls of his duplex.
  22. The guy who parks his car in the shed behind his house. You know, with a padlock.
  23. The guy who, on our second date, suggested we carpool downtown because he had a “really great parking spot.” The parking spot was a mile away from where we were going.
  24. The guy who invited me to dinner on our second date, then asked me if I minded paying for my own. Then he says to me, “I”ll get your drink though” and gave me a wink…as if paying for my $4 drink was a favor. 
  25. The guy who gave me two craft beers on our second date because I told him I was into craft beer–in truth, it was a thoughtful gift, but I had a terrible gut-feeling about him. Later in a text message he was very forward with me about progressing the relationship, so I told him that he was moving a little too fast for me and that I didn’t want to have another date. My gut feeling about him was correct: He got angry with me, and demanded that I give him the beers back. As in, threatened me. I told him that he could get the beers from the nearest police station, if he so liked.
  26. The guy who I wasn’t dating, but this is still a dating story: My good friend liked him, and we all went out one night dancing. He put a kiss on me, and I told him that I wasn’t into him. He disappears, and next thing we know we’re all asked to leave. We still don’t know what he did to get all of us kicked out, but the manager was clear that it was his fault. When I reject guys, clearly they go crazy.
  27. The guy who, when we were messaging on the dating app, had an entire conversation using Beyonce lyrics. I was hopeful. But in person…..his personality was terribly dry. Just awful.
  28. The guy who wanted to take me out to a nice breakfast, and we ended up at Perkins. I’m not knocking Perkins, just don’t tell me Cracker Barrel is gourmet.

Apologies to the men who are reading about themselves. Maybe next time, to the next woman, try not to be so lame? ;)

**As an aside–the picture that I picked for the header to this post is from Breakfast at Tiffany’s, and I used to joke that it was my dream come true to kiss a man with a cat between us. How my life has become just that!

 

3 thoughts on “28 More of my Worst Dating Moments

Add yours

  1. Good grief. I can’t believe my own gender would do some of these things. What a shocker! Apart from the obvious harassment and inappropriateness of much of it, the whole propositioning for sex from pastoral staff…wowsers.

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