Dating Over 50: Taking the Leap

A cute couple dating over 50, laughing and holding hands on the beach.

If you’ve been married or in a relationship for a long time, the thought of dating again can make anyone break out in a sweat and want to binge watch rom-coms on Netflix. Not to worry, you can do this. Here are seven things to keep in mind as you begin the adventure of dating over 50:

Don’t even think of it as dating.
Instead, think of it as an opportunity to fling yourself out into the universe and see what comes back. Chatting up someone in line at the movies or the market is always a good idea. You never know where little moments of connection can lead. One of my personal favorites is asking directions from the handsome guy on the corner. (He doesn’t need to know that you’re anything but lost.)

Switch it up.
Men tend to go out on their own and are comfortable at a bar or event. Women, on the other hand, like to go out with their gal pals. So we have men in sports bars and women in wine bars. Unless you want to keep meeting your own kind, switch it up. Ladies, it won’t kill you to go to a game now and then. And don’t go out with a gaggle of gals. Do you know how hard it is for a man to approach a group of women to start a conversation? Go out by yourself sometimes.

Find a local spot to make your own.
Remember Cheers? The eponymous TV show/bar where everyone knows your name? I’m sure there’s a place like that near you where you can be comfortable. I know the best bartenders within a 10-mile radius of my apartment. I tip them heavily and they take care of me whether I’m with friends or on my own.

Dress the part.
Men, going to a fashion event may help break you of the Hawaiian shirt phenomena, while giving you access to many lovely ladies. And please, wear a sports jacket! Every man looks good in one and a white button down shirt is classic. Ladies, on the other hand, could button up a bit. Leave the cleavage and high slit skirts for later in the game. Mystery matters!

Make room for surprises to happen.
You know when you travel to a new place, how things tend to happen? It’s because you are out and about and don’t always know what’s next. That’s a good way to look at life where you live. You don’t have to plan everything—Live in the moment. Explore. Go to a museum. Or to painting night at bar. You may even discover a hidden talent.

Don’t be afraid to make the first move.
Men typically take the initiative and approach a woman first. But I think waiting for anything is over. The last time I batted my eyelashes at someone across the room, it looked like I was suffering from dry eye. When you’re on a date, and feel the moment is right for that first kiss, do it. You’ve been around long enough to trust your instincts. In less intimate situations, be prepared to make the first move too. Always carry either a business or a personal card. You can get really fun ones made online. Customize them with your pic and don’t be afraid to give yourself a tagline. i.e. The last good woman on earth. (Oh wait, that’s mine.)

Don’t take it too seriously.
Keep in mind, the human condition is agonizingly funny. We all make fools of ourselves at one time or another. So laugh, flirt, and enjoy this time. You will never be younger than you are right now! Even if there isn’t that one grand love, there will be other things. With any luck, there will friendship, maybe romance. And if there is a god, there will be dancing! Find the humor in life and maybe you’ll meet someone ready to take the leap with you.

P.S. As I was writing this article, I met a guy at a café! A younger man. But that will be another story.

Diane Sinnott

Freelance Writer

Dianne is a freelance writer with heaps of experience dating in New York and San Francisco.

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