Dating for Success: Dating Second Time Around

We broke up a year ago. Should we give it a second chance???


At first your dating was going well but at some point you decided not to continue. You might have had a devastating break-up, or perhaps you both agreed that things weren’t working out. At the time, ending it seemed like the right decision for at least one of you.

Fast forward to sometime in the future – months or years later – and a friend’s great idea for you happens to be the person you used to date. Or you cross paths with your former dating partner at a party, a Shabbat dinner, or a business conference, and you realize the attraction’s still there. You think about dating each other again. Is it a good idea?

It depends. Ask yourself what’s happened in your life since your breakup. Life circumstances change and people change. The reason you broke up may not be relevant any more. Both of you may be wiser, more mature, more flexible and more ready for marriage than you were when you dated the first time. Twenty-seven year old Tina is more worldly and self-confident than the unsophisticated small-town Tina who dated Craig four years ago. She remembers thinking that he was a “nice guy” but felt overwhelmed by his self-assurance and ambition and decided not to continue seeing him. When they meet again, sitting next to each other at a Friday night Shabbat dinner, they ease into a comfortable conversation that continues long after the meal ends. Tina wonders, “Is Craig less intense, or am I just more comfortable with him than I was when I was younger?” and decides she’d like to date him again.

Melissa never wanted to get serious with any of the men she dated. No one felt right to her. After seeing a succession of roommates develop close relationships and get married, Melissa decided to confront whatever was keeping her from having a relationship. An insightful therapist helped her work through her feelings of resentment, distrust and fear, and in time Melissa felt ready to date with a view toward marriage. A friend wanted to set Melissa up with a man she had briefly dated a few years earlier, and Melissa felt that this time, she could actually look forward to going out with him again.

There are other situations in which it is worthwhile to consider dating someone a second time:

Jacob dated many women when he was in his twenties, but was never really anxious to get married. Now that he is 32, Jacob has decided that he is finally ready to build a life with someone. He’s heard that Sharon, who broke up with him a few years ago because he was not ready to move forward, would consider dating him again if he really has become serious about getting married. It’s been six months since Cheryl broke up with Danny. She’s done some soul searching, and realized that she made a mistake. Danny had the qualities she was looking for and she really cared about him. She’d been worried what her friends would think, since Danny was less polished than the men she usually dated. Looking back, Cheryl realizes that this was the wrong reason to end something with so much potential, and has asked a friend to approach Danny about the possibility of resuming their dating.

Because people’s outlook, values and sense of who they are can change as they mature, a relationship that seems improbable at one point can look very different some time later.

If you’re dating for marriage and are thinking about starting a relationship with someone from the past, first ask yourself these questions:

Do we have compatible values and goals? Are we headed in similar directions in life? Does he/she have several personal qualities that are important to me? These are prerequisites for any potential relationship.

Then ask yourself the following:

How have I changed since we stopped dating? What have I found out about the other person that tells me he or she may have changed? What’s different in each of our lives that makes this person sound like a possibility for me now?

What’s the reason we broke up the first time? Be honest with yourself about this. It could be that the passage of time has colored the way you remember your first go-round, so that you recall more of the good time and less of the negative ones. Were there differences you couldn’t resolve? Character traits you disliked and couldn’t ultimately accept? Behaviors or other issues (like fear of commitment, an addiction, emotional instability) your dating partner needed to work through? They may have receded from your memory, but they won’t magically disappear in real life. And if they’re still present, they’ll probably be the reason you break up a second time. Is it possible that the changes we’ve gone through will enable us to resolve the reason we broke up? Have our life circumstances changed enough so the issue no longer bothers us, or isn’t relevant anymore? If something that was a major obstacle to our moving forward is still an issue, are we both willing to discuss it now and try to reach a compromise or solution?

If you both feel reasonably confident that the reason you broke up is no longer relevant, try a second time around.
While you can’t expect to pick up where you left off, you will probably know enough basic information about each other to skip the uncomfortable first stage of dating. Your conversations can be more focused on and purposeful and you can feel comfortable enough to have fun together. You may find out that while your first round of dating didn’t work out, the second time around is the right one for you.