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What to Do if You’re Horrible at Dating


I recently wrote a post called “Three Easy Ways to Ruin a First Date,” which provided advice on how to make a first date want to run away from you and never call back. My suggestions were:

1) Propose (or at least talk about marriage enough to make yourself sound desperate);

2) Overshare negative information about your life and relationships; and/or

3) Interview your date with a subtly-judgmental attitude that says, “I’m scrutinizing you to see if you deserve to be my spouse.”

The feedback I got from the article was interesting. A number of people recalled being the victims of these date-ruining techniques, but there were a surprising number who confessed to being first-date failures. If you happen to be in the latter group, then I’d be willing to bet that behind that confession is some serious discouragement. And before you know it, you’re listening to a voice of that old, familiar, toxic logic …

If you can’t even get the first date right, you’ll never get a second date.

And if you can’t make it to the second date, you’re never going to get married. 

The end.

Case closed. 

All is lost.

If you’re lucky, you’ll meet someone in the nursing home someday.

Listen, before you plunge into another negative, downward spiral of self-loathing over how bad you are at dating, let me share a little secret with you: On my first date with my wife, I’m pretty sure I did all three of the dating fouls I mentioned above. I mean, I didn’t propose, but I indirectly brought up the topic of marriage. Common sense told me to stay away from it, but one of my favorite things to talk about on dates was dating, which eventually led me to talk about the whole point, which was marriage, which was awwwk-ward. I also found myself helplessly oversharing about somewhat-negative past church experiences (by the way, with the right set of stories, that topic can get really intense, really fast). And finally, I asked so many probing questions that my wife now tells people she “felt like she was on a date with Barbara Walters.”

Yet somehow, even though I broke all the rules for being a good first date, my wife decided it made sense to go out with me again. And believe it or not, nine months later, we were married, which naturally begs the question: How in the world? The answer: My wife chose to go easy on a guy who was clumsy at dating. She didn’t take my awkwardness too seriously; she chose to focus on the things in me that were attractive; and ultimately, she gave me another chance after that first date.

As we went on successive dates and spent more time together, I felt the freedom to be the real me. And as the real me got to know the real her, we quickly began to see that we had stumbled onto something special: grace. We belonged together, and what could’ve been another first-date failure became an endearing part of our story, but it only happened because one person gave another person space to be imperfect.

If you’re a klutzy dater like I was, stop — before you log back onto your profile, before you finally text your crush, before you post another selfie on Facebook and hope he sees it — stop, and pray for grace.

Ask God to send someone who won’t freak out on your next first date if you’re a marriage-obsessed, oversharing, Barbara Walters impersonator. Pray for someone who will be patient on the second date when things don’t go much better. And pray for yourself; pray you’ll have the grace to believe that God’s eventually going to take one of your awkward first dates and make it an endearing part of the story He’s writing for you and your future spouse.


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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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