My 26 Most Memorable Dating Moments

Millennial in Ministry, single in ministry, women

I recently read the new book “Modern Romance” by Aziz Ansari.loved his book, even though it was written from a “secular” point of view–often times when Christians write books about dating and romance, it really misses the mark. They tend to focus more on what it means to “protect your heart” and “save it for marriage,” but forget to talk about the realities and practicalities behind dating. It’s as if these books don’t understand the culture, and assume you’ll find someone who shares the same morals as you easily.

It’s just not that easy. And because dating these days is not easy, I aggressively do so. I go on handfuls of dates, and although they rarely go to a second or third date, I get lots of great stories and free dinners. Life could be worse.

I’ve wanted to share my experiences for a long time, and I’ve refrained because (1) it’s my business and (2) I didn’t know how to share them. I’ve joked about starting a blog called “Evangelical in the City” where Christians share horror stories about dating. But I’m learning that if we don’t talk about the things we are struggling with, then we won’t be able to reconcile them. So I’m sharing some stories here. Maybe one day I’ll write a book of my own.

So, here is my list of my strangest dating moments from the past 8 post-high school years. And since I turn 26 this week, I’ve made 26 points–some of them are from the same dates/men, but I split them up.

  1. The guy who talked for ten minutes about the types of video games that he likes and then said, “There’s just something about unloading a gun into a crowd of people.”
  2. The guy who was reading his thick study bible as I walked in, and if that wasn’t enough, brought out a journal of handwritten hymns and used it as something to gesture with while talking.
  3. The guy who sincerely asked me if I could curse or drink alcohol because I’m in ministry.
  4. The guy who called himself a beer snob and then drank 4 Coors Lite back-to-back.
  5. The guy who did the same, but with Bud Light.
  6. The guy who was with me as I ran into a former boss at the go-cart rink. And then his go cart broke and I felt like I had to slow down for him, even though I could have rode circles around him. Okay, so maybe this one wasn’t all on him. But the next two were him:
  7. The guy who analyzed why I wouldn’t eat all my ice cream (not because I’m fat and self-conscious. Because I was on antibiotics for a double ear-infection).
  8. The guy who at the end of the atrocious date, told me that he didn’t want to see me again. Then he hugged me and told me “You’re a beautiful woman, Heather. You’ll find somebody someday!” Then he gave me this weird puppy-dog face.
  9. The guy who I had a lovely time with at the park playing games with and feeding ducks, but apparently his mom was running laps around the park watching us.
  10. The guy who didn’t ask me a single question our entire date. I led the entire thing.
  11. The guy who did the same thing, and I refused to fill the space and tried to allow him time to ask questions. He then comments, “I can tell you over-think things a lot.” Judgey.
  12. The guy who talked a ton about how he grew up on a farm and never watched TV until college. He moved to Indiana to go get a degree from an unaccredited Bible college. Indiana was CULTURE to him and everything was mind-blowing. After 45 minutes I had to bust out of there.
  13. The guy who said, “You seem like an empowered woman who will want to pay for her own food” as we order. And you seem like a chivalrous guy who will want to pay for me, anyway.
  14. The guy who read “Wild at Heart” after our third date and realized he wasn’t man enough to date me. He joined a men’s Bible study/cult.
  15. The guy who told me on the first date he considered himself a feminist. On the second date he took me to see an extremely sexual movie, and then mentioned he appreciates modern-day feminism’s culture of unapologetic sexuality. Oh.
  16. The guy who told me his dad was a preacher of a huge church until he read his son’s Left Behind books he got for Christmas. Now he has a church of 30 he preaches turn-and-burn passages to every Sunday. I may have joked that this was all his fault…
  17. The guy who related everything we talked about back to his Catholic culture and then rebuked me for being ecumenical.
  18. The guy who told me on the second date that his dad’s house was possessed by demons and that he gets possessed every time he goes there. But I’m the weird one in this story, because I still dated him.
  19. The guy who told me he was like Buzz, I was Jesse, and right now we’re just on the hunt to find Andy. After rewatching all the Toy Story movies, I don’t think he understood what he was talking about.
  20. The guy who was a teacher at a school I have students at, and he told his entire department I was his girlfriend after just a few dates–and I found out because his coworker told her best friend who told her daughter who interned for my coworker.
  21. The guy who told me his drink of choice was Mountain Dew. I can’t trust a guy like that.
  22. The guy who came into my apartment and immediately comments, “This looks so twenty-something white girl. I think I’ve seen these curtains at Target.” No, I actually made them…
  23. The guy who told me I wasn’t allowed to wear dresses anymore because he was so attracted to me in them.
  24. The many, many men who have told me they don’t think women in ministry is a thing (and that I’m sending kids to hell).
  25. The mom who tried to hook me up with her kid who had just left for college (in her defense, I was 20, but as the youth director it was still mildly inappropriate).
  26. The guy who I “fell in love with” when I was 14 and yearly adds me on FB, deletes me when I say I’m not interested, and then always comes back around. Going 12 years strong.

My apologies to the men who are Googling me right now to stalk me before we get serious: you may one day turn into a blog post.


9 thoughts on “My 26 Most Memorable Dating Moments

  1. I just read this, and I’m laughing so hard and yet I have so many questions. Why is your dating life so hilariously tragic? Why has one person had all of these cringe-worthy experiences? Why do I want to sign up for whatever dating service you use so that I too, can cringe at the memories? Where are the single Christian men who are not weird?

    1. Girl, if I knew the answers to any of this, I could make money. Some of it is unique to being in ministry–some of the things guys have said to be could go in another post. Haha. But a lot of it is just misfortune.

      1. He brought those out because I said my church was popular for liturgy, and he came from a hipster Cali church. So he wanted to prove to me he could do hymns, too. Again, some of this is because of my position. I hope he doesn’t do that to other girls, too. He also moved to Indy from Cali on a call. He works at Starbucks. I later found out he felt like God called him here to obtain a wife. Baaaaaack outtttttt slowlyyyyyyyyy.

  2. OK, so I had to come here after reading your latest. Another cracking list. I particularly enjoyed laughing out loud to the dude who had his mum running around the lake while you’re feeding the ducks…LOL.

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