Dating After Divorce in Your 50s — 9 Ways for Men & Women to Start Over

We were in his car when his cellphone rang. I then became an involuntary eavesdropper to one side of a very heated conversation. Before my very eyes, this man changed from Dr. Jekyll to Mr. Hyde. He went from amiable and agreeable to angry and agitated. I would have excused myself to give him some privacy, but I was trapped in the passenger seat. After he hung up, he apologized, saying that even 10 years after his divorce, his ex-wife still made him crazy. We both tried to shrug it off, but the date flatlined.

Dating under any circumstance can be anxiety-inducing, but for people who have been through a divorce, it can even feel daunting. Reentering the dating scene after divorce often makes even the most confident people feel like self-conscious seventh-graders at the middle school dance.

You might be more than a little rusty if you’re just starting to date again, but these practical tips (for both men and women) can make the transition easier.

Divorce can leave deep wounds, painful memories, or feelings of betrayal. If you are experiencing deep, residual emotions, please seek support to aid your healing. While this may take some time, it will give you the advantage of being ready for a healthy relationship with someone new.

No matter what has happened in the past, this is a chance to start anew. Glean essential wisdom from prior relationships, but leave the guilt, shame, and cynicism in your rearview mirror.

If you can see the opportunity to date as a new adventure, it can help you move through any apprehension.

Talking incessantly about your ex in either a positive or negative way can be a real buzz-kill. Many a date has been spoiled by the ghosts of exes past. When you’re on a date, be attentive to the person you are with and avoid ruminating over past loves. You’ll both have a much better time.

Date several people before jumping into an exclusive relationship. It can be tempting to get involved very quickly after a breakup or divorce. You might want to fill the empty space in your life or show your ex that you can still attract a new partner. This is seldom a good idea. Remember chemistry is not always indicative of compatibility, so you want to make sure you know what you are getting into.

If it’s been a long time since you have been active in the dating scene, you’ll likely find that many things have changed. If the last date you went on was the senior prom, it’s unlikely you’re current on things like online dating. That having been said, if you are willing to experiment, you just might find it’s easier than ever to meet new potential partners.

Trying new things also means dating outside of your type. Many men and women have a penchant for a certain kind of person they feel attraction for, especially when it comes to physical attributes. It’s fascinating to see how often people gravitate toward someone who looks or behaves like the ex. If you have a pattern of failed relationships, this is the perfect time to explore your options. You may be fortunate enough to meet someone who is a better fit for you, even if you wouldn’t have thought so at first glance. Be willing to look a little deeper.

Be aware or you might project your beliefs, anger, or pain from your past relationship on to someone new. For example, if you believe men are untrustworthy or women are overly emotional, you might overreact to something innocent a new dating partner says or does. Don’t expect them to be perfect or expect them to right the wrongs from your past relationships. A new person in your life deserves to start with a clean slate.

After a failed relationship, you’re determined to get it right this time. This can create undue pressure on a budding romance. You don’t want to get hurt again, so you might be tempted to put your date through a rigorous line of questioning that feels more like a job interview than a conversation. You can learn a lot from listening and observing as things progress naturally. It takes time to get to know someone, and it’s worth the investment.

It’s essential to remember dating is supposed to be fun. Don’t sap all of the joy out of it by overanalyzing every little thing or by trying to figure out if someone is your perfect match when you first meet. There’s time to sort all of that out after you know each other better.

While it’s natural to have some fear, that emotion is always an obstacle to love. Many things you fear never come to fruition and fear can keep you stuck in a rut. You deserve to find happiness and you’re more likely to find it when you start interacting with all of those fascinating people of the opposite sex.

After some initial hesitancy about getting back in the dating game, you’ll likely find it very rewarding. Take baby steps in the beginning if you need to, and try to avoid bringing your perceived baggage with you like my date did. Don’t wait too long to get back out there, though, because the world is full of new people for you to meet. Even though it might feel like it now, your life is not over just because you have been through a divorce.