Should You Reunite With Your Ex?

Posted by in dating after divorce, single women over 40 | 3 comments

Reuniting with an ex is a big question for us dating coaches. Should you get back together with an old boyfriend? Many divorced women and men reunite with their first love decades later. It even happened to me. Last year, my first boyfriend got divorced, and we began to reconnect by email, which soon led to long phone calls. Find out what happened to me in the following article, which ran on Monday in
Should you reunite with your ex?

By SingleEdition

If you’ve secretly hung onto those old love letters or find yourself tempted to reignite the spark with an old flame, you’re not out of the ordinary.

Some of you may recognize the name Donna Hanover – she is the ex-wife of former New York mayor Rudolph Giuliani. Don’t feel bad for this former first lady, she has a “happily ever after” story and is living proof that first love is everlasting. Several years ago Hanover reunited with her high school sweetheart more than three decades after their breakup in college.

In her book released soon after, “My Boyfriend’s Back,” Hanover chronicles the timeless reunion tales of couples, raising the question which many of us struggle with years after the love is lost: “What should, could or would have happened if you stayed with the one that got away?”

If you’ve secretly hung onto those old love letters or find yourself tempted to reignite the spark with an old flame, you’re not out of the ordinary. According to, a new online surveying tool, 71% of women polled have kept love notes from an ex-flame and another 64% of them admit to days, weeks, even months where they cannot get a past boyfriend off their mind. And while some individuals are satisfied with clinging onto the fantasy, a whopping 67% of respondents have reached out to an ex-flame to test if the torch still burns on both ends.

Unfortunately not all reunion stories lead to a fairytale ending like Hanover’s. For Sandy Weiner the prospect of a sizzling meeting with her high school sweetheart began over email and telephone but fizzled out once they met in person. Weiner, who is a professional dating coach herself, admits that “while it was fun to catch up face to face, she and her high school boyfriend were like two awkward sixteen year olds” only now they were grown strangers. “Our elaborate phone plans for a relationship rendezvous,” she confesses “never happened.” The fantasy of who her ex might have become was unfulfilled and the reasons they broke up so many times from age 16 to 21 were still the same.

There was a time when breaking-up meant out of sight and mind, but the barriers that once kept exes at a distance have all but disappeared. There are auto-alerts reminding us of people with whom we should reconnect or say hello based on high school, college or friends we have in common, and tools that give free access into other people’s lives right down to the street level, thanks to Google. It’s hard not to take the bait when you find out that someone you once dated is newly divorced or just moved to a town near you.

Dating coach Tina Tessina, a.k.a. Dr.Romance, encourages singles to go for it — as long as it’s done properly. Here are Tessina’s tips on moving forward without jeopardizing memories of the past:

1. Understand Your Motives. Consider seeing a therapist on your own to get expert help to determine if you’re searching for this old love for the right reasons.

2. Try to Be Innocuous. If you see the old love on Facebook, try sending a message asking to be friends. Don’t say anything about still having feelings. Your old love may very well be married now, or even gay. You need to find out what’s going on before making a move.

3. Be aware if forgiveness is needed. Did you hurt this person’s feelings way back in college? Were you hurt? Old, unresolved feelings can linger a long time, and erupt when you least expect it.

4. Don’t move too fast. If you get a positive response, go very slowly. Rushing into things means you’re trying to avoid some truths. Slow down. If it’s going to work, it’s better if you go more slowly, and you’ll have a chance to build a better foundation than before.

5. Treat it like a new relationship. Start from the beginning, and do it differently – it could work this time.

6. Analyze what went wrong the last time, and consciously try to do it differently — talk about it with your old love — if you cannot talk honestly about what went wrong and what to do differently, you’ll never change anything.

7. Make sure both of you are equally determined to correct the old problems. If he or she is blaming you for everything that went wrong, disaster is imminent. If you’re blaming your ex, it’s just as big a problem.

8. Insist on couples therapy for both of you. Pre-commitment therapy can help you find out the pitfalls and whether you’ve solved the old problems, and also how realistic you are.

It’s easy to romanticize the past, just make sure you’re living in the present before reaching out to your former first love. is the premier lifestyle destination for singles women and men of all ages who have never been married as well as those who are divorced, solo parents or suddenly alone.



  1. I’m with you Sandy – I hooked up, after my divorce, with someone I dated for a short while in high school. He initiated the contact. The talks on the phone were fun, but in person something was lacking. I’m glad I took my time with it because his real character came out when I told him I didn’t feel any chemistry. Anger was below the surface. He had told me that I’d broken his heart in high school. Guess he never really let it go. This was just a re-enactment to him. I’ve changed so much since then and I’m sure your other readers have too. So, as many stories of rekindled love as there may be out there, I’ll bet there are even more of fires that could not be re-lit.

  2. Thanks for sharing your experience, Kathy. Similar to you, it was hard for me to feel chemistry when there was no relationship in the present. I agree, so much changes between then and now, how can one expect to immediately ignite the relationship? When I told my ex that I would love to get to know him better over time and then revisit the possibility of a relationship, he kinda dropped out of sight. I think our stories are far more common than the few who really do make it as a couple decades later. It certainly makes for good fantasy, though!

  3. This has given me hope. And that’s good enough for me. Thank you for this positive article.

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