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5 Weird Things I Did When I Was Dating

While these aren't necessarily fatal mistakes, they may be best to avoid.

I was on a date with my wife last night when I looked across the restaurant and noticed a couple who appeared to be on their first date. I did not envy them — at all.

Dating is hard. It is awkward. It is worse than a series of job interviews — or maybe it is a series of job interviews. And the frustrating thing is that only one of the interviews might even result in getting “hired” for a permanent position. So all the pressure is bound to make the experience even more awkward than it already is.

Quite frankly, I did a few things to exacerbate the awkwardness of dating back in the day. I wasn’t trying to make things awkward; it came quite naturally. Here are five of my favorite dating quirks from back in my dating days:

1. I didn’t date at all for the first half of my 20s.

Yeah, yeah — you’ve heard the story before. Somebody from Generation Y read I Kissed Dating Goodbye and went whole hog on the anti-dating bandwagon. I was one of those people, but in retrospect, I think it had more to do with the fact that the book’s philosophy complemented my insecurities and gave me an excuse to avoid women who could reject my advances. As a result, when I finally did decide to engage with the opposite sex, I had an excessive number of awkward experiences that I probably would’ve avoided if I had only engaged in more trial and error earlier on. Speaking of awkwardness…

2. I started talking about marriage way too early in the dating process.

I’ll never forget the look on one young woman’s face after I brought up marriage — on the first date. I laugh as I write this, and I wish I were kidding, but I’m not. I don’t mean to imply that I asked her to marry me or anything. But like many of my early first dates, I thought appropriate conversation topics included my expectations for marriage, my hopes for marriage, what age I wanted to be when I got married — you name it. All it did was apply excessive pressure to our time together and crush all the life out of the date.

3. Related to number two, I shared way too much information.

For some reason, I felt the need to share all kinds of personal information early on in dating. I especially had a knack for talking my family dysfunctions and previous relationships I had with other women. I would’ve been better off just asking questions to encourage women to share positive information about themselves. My oversharing felt like emotional exhibitionism, and that’s a sure-fire way to make somebody want to run.

4. I overdid it with the compliments.

Knowing how to lavish a woman with praise is a good skill to have, but like oversharing, it can get unhealthy when it is used to generate a false sense of intimacy. Back in my dating days, my excessive — but honest — compliments probably made me come off as a little overeager. It’s kind of like how Proverbs 25:16 says that too much honey will make you vomit — too many compliments can make your date emotionally nauseated as they wonder why you’re coming off as so desperate.

5. This is going to sound crazy to a lot of Christian readers, but I talked about my faith too much.

One of the most important things you can learn about a person is where they stand when it comes to matters of faith. You don’t want to be in a relationship with someone who isn’t fully committed to Christ. But as my friend Tim Schultz pointed out one time, it’s awfully easy to assume compatibility simply because the two of you are mutually interested in Jesus. I would’ve been better off in my dating days if I had invested as much time learning about who my date was as a whole person, and not just trying to make connections based on our shared faith.


Although I do think these were mistakes, they weren’t fatal. In fact, I made mistakes 2, 3 and 4 on my first date with my wife. We now laugh about them when we think back on our extremely intense first date. But even if I could’ve gone back and given myself all this advice before my first date with my wife, my dating klutziness wasn’t the end of the world.

I’m sure you have your own set of quirks that crop up when you interact with the opposite sex. Don’t kick yourself for that. Do your best to figure out what they are, make an effort to change, be gracious with yourself and then pray that God will send along someone who is gracious with you as well.

Copyright 2015 Joshua Rogers. All rights reserved.

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About the Author

Joshua Rogers

Joshua Rogers is the author of the book Confessions of a Happily Married Man. In addition to writing for Boundless, he has also written for,, Washington Post, Thriving Family, and Inside Journal. His personal blog is You can follow him @MrJoshuaRogers or on his Facebook page.


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