Post-divorce Dating Pitfalls

Mingling again after the big breakup? Heed this expert advice on avoiding four common danger zones—and on finding love.

By Kimberly Dawn Neumann

e-entering the singles’ scene can be a bumpy road, especially if you haven’t been “on the market” for a long time. As a result, re-emerging daters often find themselves face-to-face with a host of possible pitfalls, ones that can thwart even the most resilient of dating efforts. With that in mind, we gathered expert advice to help you avoid these post-divorce dating potholes. So here’s the advice you need for dating to be easier… and more enjoyable.

Dating Pitfall: You compare every potential partner to your ex
There’s probably no way around this one completely. One way or another, your ex is going
There’s no need to feel you have to make up for lost time.
to factor into your dating psyche. “Whether admitting it or not, whether conscious or not, it practically always occurs,” says Joel Block, Ph.D., relationship therapist and author of Broken Promises, Mended Hearts: Maintaining Trust in Love Relationships. “This often leads people who are dating again to look for someone different from their ex… very different.” Problems can start if you begin to overcompensate as if to correct for your divorce. “For example, if the ex was very dominant, then the person might find themselves drawn to someone one step away from a coma — yes, that submissive — and it’s not a good thing,” says Dr. Block. “I’ve seen cases where people totally overcorrect and marry their first spouse’s opposite for their second marriage. Then, they finally find a happier balance for marriage #3!”

Tactic to try: Anytime you catch your brain going into “Ex Mode,” take a time-out and recognize what you’re doing. “It’s probably not your ex-partner or date but rather you getting inside of your own head—so take a deep breath, clear your mind and stop holding yourself hostage to your past,” says Amy Botwinick, author of Congratulations on Your Divorce—The Road to Finding Your Happily Ever After and founder of Challenge yourself to inhabit your new self and see who clicks with you. Walking around with a big list of qualities a person must possess (be they identical to your ex or the opposite!) just isn’t helpful! You’ve changed and grown; there’s no need to be hung up on the past.

Dating Pitfall: You’re overcome with dating anxiety
So you’re feeling dating jitters? Join the club. Just because you’ve been out of the loop for a while, don’t think you’re the only one whose heart is pounding. Pretty much everyone feels nervous when meeting someone new. “Will he like me?” or “Will she notice my bald spot?” are not uncommon thoughts for anyone. “Learning to relate closely again is bound to be unsettling but rather than backing away, consider: Do you want to go on protecting yourself or do you want to develop a new relationship?” says Dr. Block. “If you want the latter, it is important to recognize that intimacy always involves some risk; consequently, anxiety is to be expected.”

Tactic to try: To lessen your anxiety, go on mini-dates. “A drink after work, lunch or even coffee when you have something scheduled later are great ways to ease into the scene without the pressure of an elaborately planned evening event,” says Dr. Block.
To lessen your anxiety, go on short mini-dates.
Even if you don’t have something later, pretend you do. Knowing you have a finite time limit will take the pressure off because you have an escape hatch. If things go great, you can always schedule another rendezvous. But keep first dates short and sweet until you get back into the swing. (Incidentally, the same approach goes for socializing at bars, clubs, and volunteer groups—don’t force yourself to be the first one there and the last one out. At this stage, just stopping by social events for a half-hour to an hour is a fine way to get your feet wet as you build confidence.)

Dating Pitfall: You embark on a dating rampage to prove something to yourself (or your ex)
When people re-enter the dating world, they frequently go a little wild and make some not-so-great dating choices (think “the bad boy” or “ditzy arm candy”). Post-divorce daters may feel a need to prove their desirability to themselves and others—especially if cheating was involved in the breakup. “The partner who has been cheated on feels like he or she has to prove sexual desirability; this helps validate personal attractiveness and worth. But going out and having a string of meaningless flings not only puts one’s sexual health at risk, it can also be emotionally damaging when you wake up feeling empty,” says Botwinick.

Tactic to try: Slow down! There is no need to feel under pressure to “make up for lost time.” Consider group activities which will introduce you to many new people. “That way you’re getting out and being social without the pressure of one-on-one dates until you’re ready to handle it intelligently,” says Dr. Block. Another good idea: Once you do start dating, don’t let things speed ahead too quickly. Check in about your dates with a trusted friend who has solid judgment and no hidden agenda or competitiveness with you. Then, take that advice seriously!

Dating Pitfall: You’re not prepared for intimacy
If you were in a monogamous relationship for a while but are now being thrust back into the field, it can be terrifying to think about being really, really close to someone new (you know, like naked-bodies close!). Before you dive into bed, keep the following in mind: Make sure you’re mentally ready. “If you’re not relaxed with the person, don’t get naked,” says Dr. Block. “But if it’s the first time with someone new in a long time, then know that being a little nervous when you take off your clothes is to be expected.” Give yourself the time you need to distinguish between more run-of-the-mill nerves and “I really shouldn’t be doing this yet” anxiety. Also use good judgment when considering protection—both against pregnancy and STDs. If you wait to think about this, you may find yourself in an uncomfortable situation, unprepared and endangering your well-being.

Tactic to try: First, don’t let any timetable but your own dictate when to have sex. Don’t worry that your friends and family tell you it’s time to “get out there,” or that the person you’re seeing is getting impatient because you’ve been dating for a month and nothing has happened. Learn to trust your gut. There’s no need to do what others think is best for you or what they think they’d do in your situation. This time in life is about discovering what makes you happy—whether that means having sex because you’re really ready on date number three or taking slow, gradual steps over a much longer timeframe.

Also, make sure you are prepared: See your doctor regarding protection options (or do your own research), and act on the advice you glean. Get tested for STDs if you’ve been having unprotected sex (hope not!), and make sure the other person involved does the same. No need to be cute about it. You’re both adults. Not sure how to broach the subject? Botwinick recommends saying something like “I would love to be intimate with you but I won’t do anything that will put us at risk. It’s your choice but testing and sexual monogamy is non-negotiable if you want to take our relationship to the next level.” Be smart here!

Kimberly Dawn Neumann is a New York City-based freelance writer whose work has appeared recently in such publications as Cosmopolitan, Redbook and Women’s Health, and frequently online for’s Happen magazine (
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