Dating Rules Over 50

Senior Dating

Dating “Rules” for Over 50 — (7 Vital Do’s & Don’ts From an Expert)

Ken Solin
Ken Solin Updated:
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As a date coach for women over 50 and an author who’s been writing about the subject for over a decade, I cover a variety of issues, including getting back into dating, trying online dating for the first time, and the art of asking a baby boomer out. Today, though, I’m going to take you through some of my overall top dating do’s and don’ts for singles who are in their 50s, 60s, 70s, and beyond.

1. Do Give Your Dating Profile a Makeover

If it’s been more than three or four months since you’ve updated your online dating profile, it’s time to do some revamping. Your profile can get stale after a while, and users will look past profiles that seem to be old. Add more recent photos and interests, like exercise activities, hiking, tennis, or golf because it’ll make you look like someone they missed.

Photo of a woman on a laptop

Just like your house or apartment could use some cleaning every now and then, so could your online dating profile. Even adding a new pictures and hobbies will do a world of wonders.

Reworking your profile does take a good amount of effort, but to catch the big fish, you’ve got to use fresh bait. More than four years ago, I met my now-partner online, but we had been avoiding each other on the same dating site for a year. Once we forgot about our “types” and broadened our parameters, new opportunities opened up for the both of us. There’s no exact formula to dating, but it’s not all about throwing darts at a board or kissing a lot of frogs either.

2. Don’t Date Like You Did In the ’60s & ’70s

Rocket ride relationships typically occur on or right after a first date. A couple becomes sexual immediately without any emotional attachment, and the relationship takes off like a rocket. Sadly, the relationship crashes and burns nearly as quickly once both people realize there was no real basis for a relationship beyond sex.

Photo of an old and young couple

It’s good to have enthusiasm for dating like you did when you were younger, but try to be realistic and don’t jump into sexual relationships too quickly. Photo source:

Most single boomers have ridden a fair number of rockets, and a majority of the time, they’ve blasted off hopefully but naively. Oddly, the raw nerves that result after another in a series of crashed rockets surprisingly give many boomers only a temporary pause before they board the next rocket. If you’re still willing to take a rocket ride with someone equally delusional, then consider it may be time to stop self-sabotaging.

3. Do Get Out There

Just look outside your window and you’ll see the world is waking up again. Winter is over, and if you spent those last few months not dating, it’s time to venture out. But do so in a totally different way.

Photo of an older couple sailing

Try new activities and go beyond your dating “type” — you’ll be amazed at the possibilities that open up to you.

If you’ve been fishing in the same pond for a long time, spring is the ideal season for trying a new one. Drop your old, failed type and widen your search parameters. It’ll amaze you how many date possibilities will pop up when you do so.

4. Don’t Bring Up the Ex Until It’s the Right Time

Someone who talks nonstop about their ex is someone who hasn’t healed from the breakup yet. Your date’s responsibility isn’t to be your therapist — and vice versa. A lot of ex talk also makes for a boring date, and a boring date, especially if it’s a first one, means you won’t get any more.

Photo of a couple on a picnic

Nothing will make a first date more awkward than someone talking about his or her ex. If you’re not over them, don’t start dating. If your date is holding on to the past, you should move on.

If you’re not over your ex, put dating on the back burner until you are. Spend time with friends who can help you and who care for you. On the flip side, if it’s your date who isn’t’ over his or her ex, you might want to rethink the situation. I always tell my clients not to date someone who’s been out of a relationship for less than a year.

5. Do Keep It Positive

One client of mine was on a coffee date with a man who started off by listing all of his health issues and the medications he was taking for them. This is a huge no-no. Even drug companies will save their disclaimers for the very end.

Photo of someone with tape over their mouth

Dates are opportunities to get to know each other, but you shouldn’t be rattling off all the negative things that are going on in your life. Photo source:

I cannot understand why someone would share this type of information on a first date. It’s true — a major illness needs to be disclosed. However, perhaps that should be done before the date, especially if it limits someone’s ability to function normally. But if it’s stories about your bad knee or downhill ski accident, those are better for another time.

6. Don’t Let Your Anxiety Get the Best of You

Emotionally needy dates make the other person want to scream “Get me outta here.” If you’re not willing to hold a person’s hand 24/7, you should walk away from someone who is emotionally needy.

Photo of an anxious man

Every person and every relationship has problems, but try to keep your nerves at a minimum to avoid being an emotionally needy date or partner.

Yes, all relationships have their problems, and it takes two people who’ve done the emotional work to resolve them. However, this isn’t a second-nature skill. It takes time and effort, and one person can’t save a relationship.

7. Do Leave Your Ego at Home

Remember you have to cash the checks your ego writes, so be honest and genuine about the man or woman you are. Women don’t necessarily want to meet a romance novel version of a man. In fact, most would prefer one who simply lives with integrity and treats people around him with kindness and compassion.

Photo of a man yelling at a waiter

Don’t try to win your date over by exaggerating who you are. Eventually, you’re going to have to cash the checks your ego is writing. Photo source:

Another former client of mine told me about the first and last date she had with a man who verbally abused the waiter for no reason. What sealed his fate was he continued ranting about not getting his water glass refilled during the entire dinner. Nothing is less attractive than lack of self-control.

Follow These Few Basic Tips & You’re Already Off to a Good Start!

Dating may not be as complicated as rocket science, but it still has its difficult moments. Try to find a date who is as much like you as possible, and never try to fit a square peg into a round hole. Knowing when to walk away can spare you a lot of grief down the road. Honor yourself and your values by dating someone who shares them. Good luck on your search. If you need help, I’m available for date coaching.

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