Why You Must Date The Man You'd Never Marry

It will save you a lot of heartbreak later.

woman and man standing together wearing coats Sergey Zaykov / Shutterstock

By Laura Tedesco

A few months before I met my husband, I was introduced to a guy, I’ll call him Alex, who seemed to be “the one.” On paper, he was perfect for me: well established in his career (a former athlete turned businessman), we had the same faith and similar upbringings, and oddly compatible senses of humor. My mother even approved.

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But then I met Frank, now my husband, totally by accident (in a stairwell, of all places). For a few months, I secretly dated both guys — and gradually began to realize that Frank’s assets only magnified Alex’s faults. He highlighted all the ways Alex was wrong for me — even though, if I were to write a checklist of what I wanted, Frank would have flunked and Alex would have excelled.

Alex wasn’t the only ex who helped me recognize the inherent kindness in Frank that I might have otherwise missed. There was the super-old rich guy—like, older-than-my-dad old—who woke me up to the fact that money and success aren’t everything. He was followed by a string of unavailable, but wildly successful 40-year-olds. 


And, later, there was the stereotypical jacked jock who was fun to look at but couldn’t really hold a conversation. And the doe-eyed guy who I actually started to fall for — until I realized I needed to reserve my love for a man who could text me back on time.

Even though some of these guys hurt me, each was critical to my journey. I needed to date around before I said, “I do.” I needed to learn what I didn’t want to figure out what I did.

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And experts say that’s important. “Women in our generation tend to be very proactive about what we want and how we’re going to go after it. We make lists and plans and timelines,” says Jessica Massa, author of The Gaggle: How the Guys You Know Will Help You Find the Love You Want. That’s an awesome, effective way to approach your career — but bringing a detailed checklist into your dating life puts you at risk of writing off potential matches prematurely.


Case in point: Match data shows that women often plug their “must-haves” into their online dating profiles, then end up communicating with guys that meet few, if any, of these requirements, says Whitney Casey, dating expert for the site and author of The Man Plan.

So toss aside your checklist (at least the superficial items on it), and start going out with guys that you’re a little unsure about. “In your 20s and early 30s, you have to date people who are wildly inappropriate for you,” Casey says. “That can actually help you hone in on what’s really important to you. Is it really that important that he has a four-year degree? That he lives within five miles of your dating area? Maybe not.”

And don’t view your date with the “wrong” guy as merely a stepping-stone to the “right” one. “Guys feel that judgment, and it makes them feel really insecure. So you’re not getting the best version of the guy,” Massa says.

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A better approach: Consider every date (even the man who’s totally not your type) as someone you might connect with, says Casey.

You may be pleasantly surprised to find that the guy you thought you could never marry is hilarious and has really cute dimples and makes you feel respected.

“Approach your love life like that, and you not only open your options, but you’re also more attractive to men,” says Massa. “You have this adventurous spirit, and you’re letting them be themselves.”

This attitude doesn’t require settling, and it certainly doesn’t mean letting random dudes walk all over you. You still should have standards. Massa suggests narrowing your checklist down to the five essentials (say, that he’s respectful, shares your family values, etc.), and immediately casting off any men who make you feel insecure, bad about yourself, disrespected, or who are clearly not interested in a relationship (and you are).


“Seek out the people who make you feel good and grow, instead of shrink,” she says. “You should be dating guys with the goal of learning more about yourself.”

If that means going out on dates less frequently, so be it — your dates should never feel like another item on the to-do list. “That’s dating unproductively,” says Massa. By contrast, if you’re truly enjoying yourself—the conversation is consistently good, and he makes you feel secure — then keep seeing him. And stop worrying about the little stuff. When you fall in love, all of that goes out the window anyway.

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Laura Tedesco is a National Magazine Award-nominated editor, content strategist, and writer.