Ask Dave: I Want My Ex Back!

Can love the second time around work out? Here’s expert advice.

By Dave Singleton

ear Dave,
I am 49, and about 18 months ago, I met a younger guy online (he’s 25). We met for drinks, had a great date, and got very close very fast. We started seeing each other regularly and, lo and behold, we were in a relationship—I guess. I say “I guess” because, from my end, we were just dating. I didn’t
Experts say that history ignored is doomed to repeat itself.
be different? Experts say that history ignored is doomed to repeat itself, unless you obtain rock-solid clarity.

According to psychologist Dr. Robi Ludwig, “In some cases when it’s situational, such as you are too young or your life takes you in different directions, then you can reach out and do certain things that can help you reunite.” If the breakup reasons were related more to ill-timed circumstances than to apparently irreconcilable differences, you’ve got a better shot the next time around.

So, was it just a combination of circumstance and timing that ended it? Or were there other factors, such as the age difference, that played a part in the breakup? Did age disparity keep you from getting closer to this young man? Or did you make the all-too-common mistake of not appreciating what you had when you had it? Did he show his youth by acting immaturely and impulsively when, in retrospect, he wishes he’d given you more time?

In your case, no one did anything terrible here. You don’t cite cheating, lying or seriously bad behavior, so there’s no reason why you can’t admit a mistake, or bad timing, and make a valiant attempt at reconciliation. But if you decide to try again, consider these rules before you relight the fire:

Ask yourself the tough questions. Be courageous and search within to find answers to key questions, such as:

Are you better as friends or lovers?
Sure, you are getting along well now. But the dynamics and rules of friendships are vastly different than those of romantic partners.

On some level, do you just want what you can’t have?
Is there some element of the chase and recapture that’s
Revisit the breakup to clear the air so that you understand both sides.
appealing to you? Once the chase wears off, your relationship must rely on mutual respect, love, and support.

What will be different with him this time around?
Is the fact that you love him enough? If you reunite, will he satisfy your partnership needs?

Clear the air.
You can’t just pick up where you left off. Revisit the breakup to clear the air so that you understand both sides. Otherwise, how can you move forward? Why did he react so strongly when you weren’t ready to get more serious? How does he feel about his reaction now? Why did he tell you he wasn’t relationship material? How does he feel knowing that you love him after all? Is he interested in possibly reconciling now?

Don’t let your friends unduly influence you.
Even if your friends are skeptical, your love life is not a democracy. Since they know you and can possibly see things you can’t, they get to provide valuable feedback. Listen to what they say, but remember that only your vote matters in the end. It’s not up to your friends to decide if you should reunite.

Bottom line: Explore your feelings for this young man, weed out the warning voices of friends, and decide for yourself if your life feels better with or without him as a romantic partner. Consider all of the issues specific to dating a man significantly younger than you, including financial disparity and whether there are enough shared interests. Are you better off as just friends? If the answer is no, then take the risk and tell him how you feel. Even if the romance doesn’t rekindle, your friendship will be on more solid ground.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Visit Dave’s website and send your dating questions and comments to him at
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