Dear Kat: Is Love Possible After 50?

Dear Kat, I’m about to turn 60 and I’m nervous about how that will affect my dating life. I’m not the type to go out to the bars and I’m not comfortable being on all those dating apps everyone talks about. Is there any chance for me to find love at this age?
Fabulous Fifty-Nine

Dear Fabulous,

I hear this question more often than you'd probably think. You are not alone! Let's talk about dating in your 50s, 60s, and beyond!

Many of us associate the typical dating lifestyle with younger people, but in reality, many Americans find themselves returning to dating at later stages of life. Maybe you recently divorced from your long time partner, or find yourself widowed after many wonderful years together. For some older singles, they have been in a handful of committed relationships, but never officially tied the knot and continue to date beyond middle-age.

If you’re in your 50s, 60s, or older, your love life does not have to come screeching to a halt. The great thing about matchmaking is we see clients come to us at all ages with similar obstacles.

If you’re dating in your later years, here are a few things to keep in mind.

Be Realistic

Sure, Brad Pitt and George Clooney have managed to age like a fine wine, but it’s not fair to expect the same from a potential partner. We can all control our habits and lifestyle and make sure to eat well and exercise, but it’s good to keep expectations in line. Some extra pounds or a (very) receding hairline are not reasons not to be with someone. Identify 3 personality traits or values that you want in a partner and seek those out rather than focusing only on physical attributes.

Focus on the Present

When you initially meet someone new, it’s common to feel a little nervous, especially if it’s your first date in a while. It’s a good idea to think up some conversation topics ahead of time so you don’t get nervous and dwell on the past. Try to avoid talking only about your children or your ex and focus on who you are and what you enjoy now. Discuss hobbies, books you’re reading, and future travel plans. Keep the conversation light and upbeat and save the heavier topics for a later date.

Have Fun

Just because you’re getting older doesn’t mean you can’t go a little wild! A first date doesn’t have to be a stuffy dinner or a formal coffee. Go for a walk or tour an art museum.* Make the time to text or talk ahead of time to find a date that aligns with both of your interests and keep things exciting. If you go into a first date just hoping to meet someone nice and have a decent time, then even if the sizzling chemistry isn’t immediately there, it’s still a win!

Dating at any age can be tricky, but it is often even harder to navigate when you’re older. Returning to the dating scene after a decades-long relationship is never easy but working with a Matchmaker can make it a considerably better experience. At Three Day Rule, our goal is to support our clients of all ages and help them find a compatible partner to go through life with.

Love is out there for singles of all ages!!


*Please remember to review all safety and health guidelines for any public venues or locations. If these are not options due to your location or any health concerns, there are many great virtual date options as well!

Do you have a dating or relationship question for the next "Dear Kat"? Please write to me at I can't wait to hear from you!