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Dating while 55+

Ah, the dating game. There are some things about it that have not changed since Adam picked up Eve for a garden promenade. Romance is still romance. Cupid is still targeting unsuspecting victims and rendering them hopelessly love-struck.

But there are some elements of the courtship process that are dramatically different. For example, nobody says “courtship process”. Maybe they never did. But you get the drift.

When it comes to dating over 55 and older, there are three mitigating factors to consider.

  1. First of all – no surprise here - you are not the same person you were when you first embarked upon the dating scene.
  2. Second of all, the dating scene itself bears little or no resemblance to what you remember from your misspent youth.
  3. And third of all, senior dating is a world unto itself. Suffice it to say there is a good chance you are not looking for a partner with whom to have children. A very good chance.


Who is asking out whom? Who is driving to said date? Who is paying? Who is initiating the first kiss? Back in the stone age the rules were pretty clear. The answer to all of those questions was the same. Those lines are now blurred for all age groups, but especially in the realm of older dating. Both women and men are sitting in the driver seat, literally and figuratively. There is an equality to it that makes things both simpler and more complicated. Yes, either party can call to arrange a date, and text afterwards to say they had fun and would like to get together again. But now, the anxiety comes from wondering if you should be the one. Should you wait to get in contact? Is he/she waiting for you? Or is there radio silence because they are not interested? Where once women were waiting by the phone, now everybody is sweating – and running texts by their friends to see if they are too short, too long, too needy, too pushy, not pushy enough. It’s a very different terrain to navigate. It may take a minute, but you’ll get the hang of it. Practice makes perfect.


Fortunately, today you don’t have to wait for your sister’s boyfriend's second cousin to fix you up with their aunt’s third ex-husband. There are tons of dating sites for the over 55 set. The upside is a wonderful electronically enhanced dating pool. The downside is you may be connecting with someone that nobody – including your sister’s boyfriend’s second cousin – has ever heard of. So, yes, definitely go for online dating. But yes, absolutely be aware of the potential pitfalls and exercise caution.

  • Always arrange the first meeting in a public place.
  • Always let a friend or family member know where you are.
  • If you’re communicating with someone who will never meet you in person, end it.
  • If your newfound cyber interest asks you for money, end the interchange and report that person to the site.
  • Be wary of anyone who asks you to communicate off the dating site before meeting.

There are tons of online dating success stories. With the right attitude and good common sense, you could join that happy club.

Be Yourself

There is no shortage of over 55 dating tips. Every friend and relative will want to impart their two cents. But there is really only one piece of advice that matters: Be yourself. This is your time to shine. The kids are on their own. You are footloose and free to choose whatever type of relationship you want. Your goal may be marriage. Or you may seek a regular companion who shares your interests. You may simply want a weekly dinner partner and have no interest in a more serious relationship that merges living spaces - or finances. Be honest about what you want. You’ve earned the right to be true to yourself.

Overture’s premier active adult communities offer a unique opportunity to shortcut the dating maze. Instead of spending hours online, or politely declining endless fixups, join an inclusive, supportive community designed to facilitate and encourage all manner of meaningful relationships.

The rule is, there are no rules. Your life. Your relationships. Your choice.

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