How to Make Dating After 50 More Fun and Less Stressful

Dating After 50
Debbie Reslock

By Debbie Reslock | Mar 7th, 2018

Thinking of getting back into the dating game as a baby boomer? The good news is that we know who we are and what we’re looking for. We remember the exhilaration of meeting someone new. And can now laugh at the times when it didn’t go so well.

But hopefully, age has also taught us that life is short and that it’s worth the chance to go after what we want. There is indeed someone for everyone. The trick, as always, is finding them. Before you begin to look, here are a few pointers to head you in the right direction.

You need to know who you’re looking for

Doing your homework upfront can save you time and the frustration from having to pretend you like sports, if you don’t. You’ll be more successful if you answer these 3 questions before starting the search.

  1. What do you want? Are you interested in friendship, marriage or something in between? Instead of changing yourself, this time be clear about what you want. So if you’re interested in long-term and they only want to play the field, move on.

  2. Who do you want? We’re smarter than we were back then, right? So ask the tough questions. Will you be compatible? Are they financially solvent? Can they provide references? Just kidding, but I’d avoid anyone who doesn’t have at least one friend that would vouch for them.

  3. Where will you find them? It was easier when we were younger. But in the 50+ adult dating world, anyone who you’d want to connect with is already part of a couple. That’s not factually true, but only what some of my less ambitious single friends tell me. Either way, it will take effort. You’ll have to decide if you’re willing to commit to the endeavor.

Would you like to avoid the awkwardness of a set-up?

The following suggestions have been known to facilitate meeting new and available people naturally, while circumventing what most of us dread – the blind date.

dating after 50 - ATTRACT THE RIGHT ONE

How to virtually attract the right one

And now we come to online sites for those over 50. Many find them to be the perfect place to dip their dating toes in. Just one word of caution – meeting anyone online requires a healthy dose of skepticism so always physically meet in public places until you actually get to know them.

If you’re not sure where to start, don’t worry. There’s a Dating After 50 For Dummies book and cheat sheet even for this. Here are their 10 tips for writing your online profile, which is what everyone will use to decide who they’d like to contact and maybe meet. I’ve added a few of my own insights in italics.

  1. Write in a friendly tone.
    Complaining constantly about your ex or past dating experiences can make you look like someone who’s going to be hard to please.

  2. Don’t skimp on the description of yourself.
    Looks like they’re on to us. Surveys find that women often shave a few pounds off.

  3. Be specific about what you like.
    If you only say you love the outdoors, you’ll have no one to blame but yourself if the first date involves hiking boots, sunscreen and water bottles.

  4. Avoid clichés.
    Apparently, not only does everybody like to walk on the beach but they’re also easygoing and looking for someone who’s kind. Be more unique in your description.

  5. Be honest.
    Remember, this starts in virtual reality but once it progresses face-to-face, the jig will be up.

  6. Talk about something that shows you’re a good person.
    People feel more comfortable if you show them you’re kind. Which, of course, you are.

  7. Don’t sell yourself short.
    Those same surveys in #2 found that men tend to round up a few inches in height.

  8. Don’t be arrogant.
    After talking only about yourself, asking them what they think about you doesn’t make you a good conversationalist.

  9. If you have a sense of humor, show it.
    If you haven’t developed one by now, don’t play hard to get. Being funny is often the #1 trait everyone’s looking for.

  10. Appear happy and grateful for your life.
    Most people aren’t looking to take on a special project.

dating after 50 - dare to date

If you dare to date after 50

Dating at this stage in life is different because we’re not just older but wiser. We also live full lives so most likely no one will be the sole object of our attention. We have kids, grandkids, a career or possibly parents we’re taking care of. But think of it this way, we have much more to share.

For those who’ve lost a little confidence through the years, remember how much you have to offer. Reacquaint yourself if you’ve lost sight of what’s remarkable about you. And remember that dating doesn’t necessarily have to result in romantic love. Sometimes it leads to great friends and life-long companionships.

We don’t all have to be coupled to be happy. But don’t let anxiety or fear of rejection stop you. This could be the great adventure of your life so find your courage or a friend that will help you look and jump in.

I can’t promise that the water will be fine, but I bet you’ll have fun.

Debbie Reslock

Debbie Reslock

Debbie Reslock writes about and for the baby boomer and 55+ market, including the amazing journey of aging itself. Her blog, The Third Act, can be found at


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