Reinventing Romance: Dating an Ex

Is dating an ex a good idea? Should you go back to your ex-boyfriend? Our dating expert gives advice.

By Sherry Amatenstein, LMSW

Randi Toro felt proud. She’d stayed away from the catnip that was her ex for three and a half months — the longest amount of time since their on again/off again relationship had begun three years earlier. "In the thesaurus, Ben’s photo should have been next to the word ‘commitment- phobe,’" admits Randi, a Washington lobbyist and single mother to a 12-year-old. With a sigh, she adds, "He was always happy to see me and equally happy when I left. While I wasn’t looking for marriage — I’d been down that road before — I did want someone willing to be my partner. That’s why I knew I had to make the final break."

Post-split, the 44-year-old gradually stopped thinking about Ben every day, even started finding other men attractive. But one night after catching Dirty Dancing on TV (one of her top five romantic flicks), she called him, "just to say hi…Old friends catching up." Her ex suggested dinner; food led to fondling. Randi summoned every drop of willpower to tear herself away before "dessert." After the encounter, where does she stand in her recovery? "The scabs tore off," she admits. "I’m bleeding again, back to square one, and wishing he could see how wonderful we’d be together."

Is Rehashing a Past Romance a Smart Move?

The temptation to slip back into a relationship you’ve outgrown like size 4 jeans can stem from a myriad of motives, including loneliness (where is the great guy you thought your ex was preventing you from meeting?), idealization of your former partner (suddenly his habit of stiffing waiters seems thrifty, not cheap), and missing sex (vibrators are us).

But is seeing your ex ever a good idea? Lorelei Sharkey, co-author of Em & Lo’s Buh-Bye: The Ultimate Guide to Dumping and Getting Dumped, says a relationship relapse can work, "as long as you go into it with reasonable expectations." Both partners must be on the same page, whether the goal is friendship, a friends-with-benefits situation, or a newly committed union. (It almost goes without saying that if the relationship was abusive, there is no good reason for revisiting that chapter of your life.) However, "If there’s a hidden agenda where you’re hoping to seduce him into falling back in love with you, things rarely end well."

Typically your ex is your ex for a reason. Problems don’t just magically resolve because you missed each other during the time spent apart. Don Rosenthal, co-author with wife Martha of Learning to Love, comments, "I have seen both success and failure. Success depends upon a certain amount of deepening and growth in the period spent apart." Rosenthal suggests a person who is considering moving forward with an ex ask searching questions such as, "Have I understood my own contribution to the difficulties that drove us part?" and "Do I have any evidence that my partner has learned from the past and is willing to take responsibility for his role in the dance?"

Compatibility Is Key

Nicole Hammer, 45, and her boyfriend hated being apart yet found it impossible to live together, breaking and making up 10 times in a seven-month period. Friends began joking about their "yo-yo" union and taking bets on when the couple would next implode. Nicole, a New York-based magazine editor, says, "Ken was my first great love. All my earlier relationships were lukewarm, so I took our stormy fights and reunions as a great sign of passion. I prayed that the fact that we wanted each other so desperately could make up for our incompatibilities which, yeah, were vast as the Grand Canyon."

Alas, prayers alone cannot ensure the success of an attempted reconciliation. According to marital therapist Beth Erickson, PhD, "In order for relationships to truly work, people need to share similar basic values, visions for their lives together, and at least some mutual interests." Adds Dr. Erickson, who is also a spiritual mentor and personal coach, "If couples are genuinely compatible but break up anyway, the bottom line is defensiveness." And if they don’t learn to detach their egos and stop needing to always be right, the ‘new,’ improved relationship will quickly resemble the old, unbearable one.

The secret, then, to getting back with an ex is for both partners to be different people in this incarnation. That doesn’t mean either partner should call upon a dormant personality to come to the fore; rather, both must do inner work. I interviewed Tara Cleten for my book, Love Lessons from Bad Breakups. She divorced Tom, her husband of 20 years, after he committed two infidelities. The pair remained cordial for the sake of their two daughters. Several years later, a financial crunch forced Tara to ask Tom to move back into their house — exiling him to the top floor and requesting rent. This arrangement continued for over a year. Tara, 58, recalls, "Since there was no [pressure] to reconcile we had wonderful times — lots of laughter and wonderfully heated and constructive conversations. I said, ‘How come we couldn’t fight like this when we were married?’ We also learned to clean up one problem at a time."

Eight years after their divorce, the couple remarried. "I knew Tom would never cheat again. He knows there are consequences to his actions," Tara says. She explains, "This is not the same marriage. This time around, I know he’s intelligent in some areas and stupid in others. I still love him, but I’m no longer a pleaser. And he’s no longer a taker. We are now an indestructible unit."

If you recommit in haste and for the wrong reasons, you won’t need a soothsayer to predict another breakup. But if you truly examine why the old relationship fell apart and begin the new one with commitment, clarity and — you guessed it — honest communication, the second time around just might be charmed.

Do you have a tough question about dating or relationships?

E-mail Sherry at and your question might be featured in an upcoming column.

About Sherry Amatenstein

Sherry Amatenstein, LMSW, is the author of Love Lessons from Bad Breakups and Q&A Dating Book. She runs dating seminars around the country and does private coaching — not to help singles marry in 60 days, but to uncover their blocks. She has given relationship advice on the Early Show, Regis, Inside Edition, CBS News, VHI, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.

Originally published on, October 2007.

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First Published Mon, 2009-04-06 18:07

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