Top 6 Dating Mistakes After 50

redefining after 50 self-care Jun 28, 2020
Dating after 50

The other day, a friend of mine, who happens to be the same age as my adult kids said, “Can I ask you a weird question?”

“Of course!” I said, naturally very curious.

“My mom is ready to date. It’s been 9 years since we lost my dad. Do you guys have any single guy friends?” Which got me thinking. We don’t have many single guy friends between the two of us. And I’ve got several single female friends.

Why Are We Dating After 50?

Because we’re YOUNG! And some of us are divorced. Some, like my friend’s mom, are widowed.

By virtue of being human, we are social creatures. We crave intimacy and companionship. We are not designed to live in isolation. Studies show that growing old in isolation is linked to chronic disease, depression, dementia, and even death!

At 50, 60, and even 70, we women have many active years left ahead of us. And we are wired to want to share them with another person.

Our after 50 activities are different from those of our younger years. In our 20s we were establishing our careers, running around with friends, and possibly getting married and starting our families. 30s were spent continuing down that path and raising our children. In our 40s, for many of us, our kids were teenagers and starting to leave the nest.

In our 50s we find ourselves entering a different phase. We might be looking at our career life and thinking about retirement or starting something new. Our kids are grown and we often have grandchildren. Many of us are helping to care for senior parents.

Our interests have changed. We’ve settled down and tend to enjoy quieter activities. We stay at home more on a day to day basis rather than head out to happy hour each night after work, for example. But we might find ourselves wanting to travel more. And we want to be able to continue to share all of these everyday experiences with someone we love.

It can be daunting to be faced with the idea of starting to date again after 50. Those fears of not being as young as we used to be. Not liking our bodies. Wondering how we know we can trust someone. We can be a little more set in our ways at this stage and nervous about how someone else will fit into our routine. If we are dating because we’re recently divorced, we might be lacking confidence.

Dating mistakes can be made at any age. But, the mistakes are different as women over 50. Following are the top 5 mistakes to avoid when re-entering the dating scene:

Mistake #1 – Dating Simply Because You're Afraid of Being Alone

This is a huge issue for women, particularly as we age. We don’t realize how strong we really are! Be very careful about getting back into the dating game right after you are divorced or widowed. Give yourself time to grieve if you have lost your husband.

If you have just gone through a divorce, counseling can be very helpful before putting yourself back out there. It’s good to work through some of the baggage that may be left behind. To gain confidence and know that you are strong and independent. You are looking for a partner to complement you. One who will walk alongside you. Not one who has to lead or one who always wants to follow.

Facing the idea of being alone can be very scary – especially for a woman who has never done it before. Many of us went right from home to college with roommates. We then lived with roommates after college. Then got married and had children. Many of us have never lived on our own and find ourselves navigating this new path after having lived half of our lives!

Don’t start dating out of a place of fear. Work through that fear before moving forward. Otherwise the process will be pressure filled and not fun at all. Fear is a turn off and people can sense it. Come into the process from a place of gratitude and confidence.

Mistake #2 – Bringing Your Baggage With You

This is closely related to mistake #1.

We all have baggage. Leave it at the door. Going to counseling before moving forward with dating can help you work through this. And it will make for a much more successful dating experience overall.

Getting counseling before starting to date will not only help you get rid of your baggage, it may help keep you from repeating past mistakes. The best advice that I ever got from a counselor was when he said to me, “When you walk into the party and you see the man that you want to strike up a conversation with, turn around and walk the other way!” In other words, I was repeating the same mistakes over and over and choosing men who were emotionally unavailable and emotionally immature.

I took his advice and am today very happily married. To a man who is totally different from all others that I’ve dated.

Mistake #3 – Jumping in with the Sole Purpose of Finding a Mate and not Enjoying the Process

Entering the dating scene putting pressure on yourself to “find the perfect mate” rather than just enjoying the process will not be fun at all for you or for your dates.

Enter this dating journey with the mindset of meeting new people and enjoying new experiences, restaurants, coffee shops, etc. With the mindset of getting out and being social. And with the mindset that “today I’m going to meet a new friend!” Enjoy the conversation. Learn about someone new. The rest will follow.

Make affirmations like the following your mantra:

“It’s not the destination, it’s the journey.”

“I am living in the present. I am smelling the coffee, enjoying the conversation and the sunshine. Life is good.”

Mistake #4 – Refusal to use Online Dating Sites

Women in our age range are often concerned that they will be conned or taken advantage of if they use an online dating site. Be confident and trust your gut. You’ve got a lifetime of experience behind you now. You won’t ignore those red flags if they arise.

There are several online dating sites that are geared to persons over 50. Using these sites enables you to be in contact with many more people than you would be if you were relying on friends to introduce you. Only use paid websites. You do get what you pay for. If you do that and follow these rules, you will be as safe as you can possibly be. There are risks in everything we do. Be smart and you will likely end up having a blast!

Don’t lose sight of Mistake #3. Just go out and enjoy getting out, being social, and having great conversation.

Mistake #5 – Not Realizing Your Value and Trying to Present as Someone You Aren't

Be you! It’s too much effort to try to be someone else and why would you want to?

Mistake #6 – Talking Heavy Stuff on the First Date

Keep it light. Get to know each other – likes, dislikes, kids, grands, books, movies, etc. Steer clear of politics and why you hate your ex-husband. Make small talk, chit chat and look for commonalities. Pay attention to how much you truly laugh. This is a good sign.


Dating, particularly for women over 50, can be an intimidating prospect. We are worried about how we look as we age. Men can get away with dating younger women and they often do! We tend to live longer than men do also, so there are more of us!

As my good friend says to me anytime I’m anxious about a situation, “Just walk in there and flip your hair and show them who you are.” And don’t ask yourself “What’s the worst that can happen?” Instead, ask yourself, “What’s the BEST that can happen?”

Enjoy the journey. The experiences. And being in your own skin. The rest will follow.