How to Date an Ex-Boyfriend

Smiling couple in restaurant
It's hard not to worry about history repeating itself when you reconnect with an ex. (Image: Polka Dot/Polka Dot/Getty Images)

According to the lyrics of a 1960s song penned by Sammy Cahn and Jimmy van Heusen, "Love is lovelier the second time around." In reality, however, psychologist and couples therapist Dr. Joel Block cautions that not every rekindled romance with an ex is guaranteed a happier outcome than what happened before. If you plan to give your ex-boyfriend a second chance and resume dating, it's important that your open mind and forgiving heart are balanced by a healthy respect for your own self-esteem and self-worth.

Step 1

Make a list of the reasons you and your ex-boyfriend parted. Examples of this might include different interests, goals and values, incompatible schedules, dishonesty, infidelity, physical or emotional abuse, or just not being ready for the responsibilities of a serious relationship. Ask yourself what has changed while you've been apart that has affected or resolved these issues to your satisfaction.

Step 2

Define the reasons you want to give him another chance. Among the best reasons to reconcile are that you've always cared about him, that you feel you've both grown emotionally, and that you're willing to acknowledge your own contributions to the breakup. Seattle Weekly's "Dategirl" columnist and book author Judy McGuire cautions that women often rush back into the familiar arms of a former boyfriend because they're lonely, depressed, discover they're pregnant, or have just been dumped by someone else. None of these, she says, are good reasons to date him.

Step 3

Find out whether your ex is as interested in getting back together as you are. If you're the one initiating this move, you can glean this information from his friends or ask him directly. Rather than put him on the spot in person or set yourself up for an awkward rejection, however, you might want to send him a "thinking of you" card or leave him a phone message. If he's the one who wants to reconnect with you, it's then up to you to decide whether he's committed to a fresh start. In his book, "Broken Promises, Mended Hearts: Maintaining Trust in Love Relationships," Block emphasizes the importance of trusting your instincts. If you don't feel comfortable, say so.

Step 4

Arrange to get together at a neutral spot to establish the ground rules for moving forward and dating again. Psychologist Dr. Shirley Glass, an expert on infidelity issues, stresses the importance of insisting on personal accountability. If, for example, you broke up with him because he was cheating on you, it needs to be clear you have zero tolerance for him continuing to have a relationship with the other woman in person, on the phone or via email. As part of the healing process, she also points out that you, in turn, need to let go of your suspicions and obsessions that every time he's now out of your sight he must be cheating.

Step 5

Revisit favorite places to remind yourselves of the happy memories you created together. According to McGuire, it's also important to try out new things and experience one another in settings that aren't familiar to either of you as part of the reacquaintance process. This is especially important if you take your ex somewhere you used to go with an interim love interest. The last thing you want to do in your rekindling phase is to make him think you're making comparisons.

Step 6

Recognize when the second chance has run its course and it's time to close the door. Block defines trust as feeling physically secure and emotionally safe. It further requires both partners to respect each other's needs and to communicate if these needs aren't being met. While it's certainly possible for two people to build a stronger union the second time around, Block points out that one or the other often brings unrealistic expectations of success that create additional pressure and stress.

Tip

Let your friends and family know that you're thinking of dating your ex-boyfriend. While the decision is ultimately yours, these are likely the same people who were your sounding boards when he was making you so miserable. Use them as your reality check if you're not sure you're doing the right thing.

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