Uncommonly Candid Observations on Relationships: The Dating Game After 50 – Or Perhaps Any Age

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“Eighty percent of success is just showing up.”– Woody Allen


It’s not difficult to find women over fifty, or for that matter at all ages, who are unhappy about their dating lives. Some say it’s difficult to meet men. Others say those they meet online don’t measure up. A few seem resigned to failure. These women are not kids; they’ve been around for a while and most have been married or in long-term relationships.

I’ve had my share of relationships, and as the author of a memoir, I am often asked if I have regrets about them. My answer is no. My belief is that you can’t sit back and watch. Life goes by too quickly and you’re going to miss it if you don’t get out and participate.

Let’s face it: we all have insecurities and lapses in confidence, not to mention expectations—all of which can trip you up unless you’re able to put them aside. And I don’t mean putting them aside forever—just for those moments when you need to feel stronger. Consider taking it just one night or even one event at a time.

Don’t want to go to the party? Do it anyway. Boost your confidence as you’re putting on a dress or jeans by looking in the mirror and saying, “I really look great tonight.” This is not the moment to think about losing ten pounds or obsessing about your nose. Indulge in a little positive self-talk about how great you look and feel. So you’re not a supermodel; the other partygoers probably won’t be either. (And don’t kid yourself; even supermodels have insecurities.) Everyone around you is pretty much in the same boat: a bit insecure, self-conscious, and looking for a connection. That’s the reality. Just remember, like Cinderella, you can return to all those insecurities later. For one night leave them at home.

An attitude of positive reinforcement builds self-esteem. Don’t just focus on the dress, hair and lipstick—pay attention to your overall bearing. Confidence creates the image you project; it’s what makes us all stand up a little bit straighter.

It’s important to keep in mind that you will be meeting men with their own confidence issues and insecurities. Try giving them the benefit of the doubt instead of sizing them up in superficial ways or assuming their motives are suspect. And, I beg you, do not say to yourself, “Ugh. If I do meet someone he’ll be at best a creep or at worst an axe murderer. (I have a friend who does that, and it immediately deflates any positive input she’s managed to conjure up.) Focus on the fact that you may actually meet a nice guy or two.

So, stop worrying and bemoaning your fate and get out and have some fun. Be positive and don’t let your own negative feedback weaken your resolve. If things don’t turn out as you hoped, try again another time. There will always be other people and opportunities that will come your way, and you’re the only one who can make the most of those opportunities. Don’t find yourself looking back later with regrets, saying, “I wish I had done that.” Instead, just do it.

And, by the way, call me when you meet that nice guy.


Marcia photo

Marcia Gloster is the author of 31 Days: A Memoir of Seduction. Visit her website.


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On March 27, 2015
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