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The Only Lethal Mistake in Dating

man alone in forest
There's one thing I won't fault myself for, and it's this: I tried.

When I was single, it was easy for me to be friends with the single women in my life, but as soon as I moved in the direction of dating, things got weird. People tried to give me pointers and steer me in a less-weird direction, but I think most of them were too polite.

It didn’t matter though — I doubt that greater candor would have changed anything. I tended to resent the few folks who shot straight with me and shattered my assumption that I was a dating Casanova. But I really did need help in the dating department, and in retrospect, there were three primary areas where I was faltering:

1. I needed to stop interviewing my dates.

When I interviewed my dates, it made it painfully obvious how much I was scrutinizing them. Women who feel like they are being scrutinized get extremely uncomfortable, especially if they’re being scrutinized over things like their physical fitness, their relationship with God, their family background and what they want to do with their lives. And why wouldn’t they? They already judge themselves harshly enough in these areas every day. They needed to be treated with deference, like royalty — not like contestants in a one-judge pageant.

2. I needed to stop oversharing.

I remember when a wise, middle-aged mentor named Ann Young politely encouraged me to “try to leave a little mystery” instead of revealing so much on early dates. I thought that was a nice suggestion, but ultimately, I shrugged it off. I mean, why not reveal everything when, apparently, everything about me was so terribly interesting? Instead of taking Ann’s advice, I continued to verbally vomit far more than many dates ever wanted to know, undoubtedly leaving them with the distinct impression that they had just survived an unwanted counseling session.

3. I needed to be more gracious when things didn’t work out.

If I asked a woman on a date and she turned me down — or worse, if we went out and she turned down a second date — I took it personally. I would then commiserate with my single friends and sulk about how so-and-so wasn’t ever going to get married if she didn’t at least give a great guy like me a chance. You know what I really needed to do? I needed to grow up and deal with the fact that these women had every right to turn me down. They weren’t responsible for supporting my fragile ego, and besides, their rejections brought me one step closer to the woman who would eventually be my wife, so I should’ve been grateful.

What I Got Right

There’s one thing I won’t fault myself for, and it’s this: I tried.

I asked out dozens of women from various backgrounds, and if they said yes, I took them out, paid for their meals, and usually acted like a gentleman while we were together. Some of these women seemed more likely to be a potential spouse; some of them seemed less likely. All of them knew that the stakes were low, and there was no reason to be thinking about the right color for their bridesmaids’ dresses. And they knew it because I explicitly told them it was “just a date” when I would call them and ask them out (yes, I called; no, I did not text and ask if they wanted to “hang out”).

So yeah, I tried and tried until eventually, providence, grace and the law of averages worked in my favor, and I met a lovely woman named Raquel. She said yes to a first date; that led to a second date; and that led to her saying yes when I asked her to marry me four months after we met.

Just Do It

And that brings me to the only truly fatal mistake you can make if you’re dating for the purpose of getting married: Don’t try. Sit on the sidelines and wait for the person you’re 93 percent sure you’ll want to marry. Don’t even bother with people who merely might be quality mates. In doing so, you’ll almost guarantee your perpetual singleness. You’ll be like a person who wants work but won’t send out applications or like a person who wants to adopt, but doesn’t want to meet any children.

On the other hand, if you simply start practicing the art of getting to know other single people, it may eventually pay off. Why? Because, at the very least, it will help you get to know your future spouse with a lot more ease if he or she finally comes along.

Yes, repeatedly diving into the dating scene will be a humbling experience that will demonstrate how incredibly inept you can be when it comes to pursuing marriage. But here’s the good news for those who are willing to take the plunge and risk putting themselves out there: Even though it won’t guarantee a spouse, it will make room for possibilities that simply don’t exist for those who don’t try.


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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