Can You Fall In Love With One of Your Ex-Boyfriends?

I am a 43-year-old woman who has never been married (although I would like to be). Over the past 25 years, I have had a number of relationships while living in the U.S. and abroad. In the great majority of these relationships, it was the man who decided to break things off with me.

I am writing to seek your take on the phenomenon of being contacted by ex-boyfriends and girlfriends. In my opinion, once it’s over, it’s over, and I move on with my life. Yet I have been contacted by a number of ex-boyfriends (three in the past three years alone) telling me how they regret breaking up with me, how still love me and miss me, and how they wish they could have another chance. The most recent contact has been from a man whom I knew 14 years ago and who lives in another country.

I don’t understand what the point is of contacting someone from so long ago in your past, especially when you no longer even live in the same city or country. Are these men just desperate and lonely? Are they living in a fantasy world? These messages throw me into an emotional turmoil because, as I said, I would like to be in a serious relationship. When I hear from these men, I begin to remember our relationship and wonder if it would be possible to get together again. My job is flexible, and I can work from anywhere in the world. So when these men contact me, I do take it seriously. Any insight? —Almita

Anyone who claims not to be selfish probably doesn’t have a clear-eyed view of the world.

Dear Almita,

I never say never.

I may win the lottery. I may get divorced. I may get pancreatic cancer and be gone before I’m 50.

I think all of these things are exceedingly unlikely, but they’re possible.

So what do we know about men who broke up with you in the past and are coming back for more?

Well, without knowing either you or them as individuals, all I can do is prognosticate, based on what I know about people.

1. People are selfish.They do what’s right for themselves first and tend to sort of hope that they’re not hurting you in the process. Anyone who claims not to be selfish probably doesn’t have a clear-eyed view of the world. It’s common sense to be selfish. To maximize your needs, wants and desires. It doesn’t mean you’re unethical. It just means you’re pursuing your own happiness.
2. People are shortsighted. We act. We react. We make the decision that makes sense at the time. Sometimes it means marrying the wrong person because you’re 27 and “in love”. Sometimes it means bailing on the right person because you’re “not ready” to settle down.
3. People grow up. I don’t know a single person my age who looks back 5 years and sees the same exact person. I knew a lot more at 30 than I did at 25. I knew a lot more at 35 than I did at 30. And, on the cusp of 40, I know a lot more than I did 5 years ago, when I was five months into dating my wife.
4. People have regrets. Some folks regret things that they did — breaking up with an amazing woman. Leaving a comfortable job for a more exciting opportunity that didn’t pan out. Some folks regret things that they didn’t do. Try writing that novel. Asking out that girl. I try to live my life with no regrets, but even the best of us have moments of “what if?”

Despite the many heartening things I said above, which may sway you to think that you may want to give one of your exes a shot, I’m still skeptical.

Because even though people regret, change, and evolve, at the end of the day, there are some things that don’t change.

Character rarely changes. A cheater is usually going to be a cheater. A liar is usually going to be a liar. A poor communicator is usually going to be a poor communicator. It’s not that it’s impossible for people, through life experience and therapy, to improve on various facets of their life — it’s that it’s a pretty risky crapshoot to consider that the disappointing man in your past has suddenly morphed himself into someone consistent and trustworthy.

Of COURSE he’s going to say he changed. His intentions may be 100% pure. But that guy is still high-risk.

Why?

I know why it might be tempting to rekindle an old flame with the devil that you know, but I’d strongly lean towards the one you don’t know.

Because he’s already burned you, that’s why!

He dumped you. He hurt you. He went away.

And now that his life is not where he wants it to be… now that he’s feeling lonely and vulnerable… now that he’s going through his mid-life crisis and can’t seem to pull off hitting on 29-year-olds in bars…

Now he comes crawling back, begging for another chance.

Is he sincere? Probably.

Is he a good bet? Probably not.

He’s the same guy who dumped you before. He’s just a lot weaker and needier right now, because of his circumstances.

Listen, I know why it might be tempting to rekindle an old flame with the devil that you know, but I’d strongly lean towards the one you don’t know.

Decline contact with your exes, start with a clean slate, and trust that the right guy — the one who will be with you ‘til the day you die — is not going to dump you the way these other 3 men did.