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Divorce Strategies: Making Post-Divorce Dating Easy and Fun

Updated on June 2, 2014
Keeping things light is key to enjoyable post-divorce dating.
Keeping things light is key to enjoyable post-divorce dating.

The thought of dating fills many newly-divorced individuals with dread.  Getting dressed up to make small talk with a stranger can be viewed as an anxiety-producing chore.  But post-divorce dating can – and should – be easy and fun.  Here are some tips. 

Don’t View Dating as the Be-All and End-All

Especially for the newly divorced, dating shouldn’t be seen as the fast-track to the next marriage or even a committed relationship. If your divorce is recent, you’re learning all kinds of things about your likes and dislikes. It’s best not to interrupt the process of getting to know yourself again with the pressure and confusion of a new romantic relationship. Each date should be seen as simply another opportunity to find out more about what you do and don’t want in your new life as a single person, as well as a chance to meet someone new.

Accept More Dates than You Want to Accept

Obviously, you shouldn’t go out with anyone you find frightening, but other than that, keep an open mind.  Remember, it’s just a date, so your prospect doesn’t need to be perfect.  This date is just one evening of your life, and if you don’t hit it off, you never have to go out with this person again.  That said, unless your first date is truly awful, give her or him another chance on a second date.  Many people are excruciatingly nervous on first dates and thus have difficulty making a good first impression.  Make the second date a fun activity, such as a community art show or picnic in the park, to avoid over-focusing on one another.

Post-divorce dating is a chance to learn new things about yourself.
Post-divorce dating is a chance to learn new things about yourself.

Keep It Light, as Far as Your Thoughts Go

Don’t spend first dates wondering if you can spend your life with this person, or worse, if you can imagine them helping you raise your children.  The only decision about the future you need to make is whether or not you’d like to see this individual for a second date.  And that decision doesn’t need to be made until the date is over.   

Keep It Light, as Far as Conversation Goes

Should you ask your dates where they see themselves in five years, professionally, when they tell you about their careers?  Absolutely, if that’s the direction the conversation takes.  Should you ask your dates where they see themselves in five years, marriage-wise, when they tell you about their past relationships?  Absolutely not!  You don’t even know if you want a second date yet, and leading questions won’t help you get to know your date better. 

In any case, tales of woe about past relationships should be banned from dates.  There’s nothing fun about hearing about another person’s mistreatment by an ex and subsequent heartbreak.  If your dates introduce this topic, don’t jump into a gripe session with both feet; instead, gently steer the conversation in another direction.

Keep It Light, as Far as Your Actions Go

Are you sensing a theme here? Yes, keeping it light is critical to dating enjoyment. And that’s true for your behavior as well as your mindset. If you invest too much emotional energy into your dates, you will quickly become exhausted simply by the thought of going on another. Keep in mind that divorce and low self-esteem are often linked; you need time to recover your sense of self before getting involved with someone else. Here are a few don’ts that will help you keep first dates light in terms of your behavior:

  • Don’t spend more than four hours on your first date.
  • Don’t call your date repeatedly, either before or after the date.
  • Don’t stop dating other people after just one date with someone else.
  • Don’t over-analyze. The only question that needs to be answered right now is, “Do I want another date?”
  • Don’t introduce your kids to your dates. This is a big DON’T.
  • Don’t take safety risks.
  • Don’t take rejection after a few dates to heart; just accept that it wasn’t right and move on.
  • Don’t forget to have fun!


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