Tips for Dating In Your 50s – Mature Dating Hacks

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Tips for Dating In Your 50s

Compared to your 20s or 30s, dating in your 50s comes with a lot of doubts and insecurities. For one, you’re probably scared of stepping into the dating world after a long time, or you feel there’s no one out there for you, so you give up on the prospect of finding someone.

Alongside this comes how you intend to show up, master the art of flirting, and, let’s get real, you just don’t feel great like you used to.

So how can you possibly get out of your head, step out of your comfort zone, and rock the entire world of dating, thus having the best experience you’ve ever had?

We flipped through books, listened to helpful insights from experts, and, drumroll,… We’ve got all the tips you need for dating in your 50s.

If you’re ready, then let’s do this!

Tips for dating in your 50s

The rules have changed, and the dating world keeps evolving every day, but does dating get easier as you get older? If you’re in your 50s and back in the dating scene, it does come with some great benefits.

However, if you intend to enjoy that, you need tips to help you thrive, which is why you have fifteen tips for dating in your 50s.

Healing and Letting Go of the Past

Your 50s are probably the most difficult decade to date if you haven’t made peace with all that’s happened to you. So, if you’ve lost a loved one, go for grief counseling, and if it’s a bad divorce, everything can be fixed through therapy. Talk to a trusted professional about it.

The path to healing isn’t easy. You’ll have good and bad days, but it’s important to get to that phase where all those things that happened in your past don’t affect you anymore.

Do you want to ensure you’re coming back into the dating world after years with the best version of yourself? Then fix yourself psychologically. Don’t skip the healing process.

Make a list of Your wants and deal breakers

According to Pepper Schwartz, a sociology professor at the University of Washington and author of Dating After 50 for Dummies, figure out what you’re looking for with the “rule of five.”

Pick five major qualities your partner must have, and then you can start being flexible with the rest. Rank these qualities with the most important at number 1, then cut off everything above number 5, and see if you can live with the idea of someone who has the first five qualities but not some of the others.

Do the same for the things you can’t tolerate in your partner. If you don’t want a smoker or someone who can’t hold down a job, it’s better to state that now and know that now so you just don’t accept whatever comes your way.

A woman in her 50s making a list about what she wants for her date
A woman in her 50s making a list of what she wants for her date

Don’t be afraid of putting yourself out there

If it’s something you truly want, then don’t let anything hold you back, not even yourself.

Be bold about your intentions; work on your confidence; use conversation starters, role-play with friends, and flirt with anyone you think has the potential you’re looking for because what’s the worst that could happen?

Also, if there’s anyone your friends or family could introduce you to, reach out to them, but don’t keep quiet about it because at this stage you need support rather than flying solo. However, if you can’t get that support, don’t hold back on doing your own thing too.

Working on Your Confidence and Upgrading Your Wardrobe

It’s probably been a long time since you went out on a first date with someone who isn’t your ex-spouse. In this case, you need to upgrade your wardrobe into a functional one.

Dating in your 50s also comes with living fearlessly, so it wouldn’t be so terrible if you decided to change your hair, start using makeup, or wear outfits that accentuate your figure. If you’re stumped on where to start, get tips from a professional in that field.

Another thing is to make a list of your strengths and achievements.

It could be raising your kids (which isn’t easy) and being fantastic with your career alongside. It could be your friends, your good health, or who you are on the inside. Do you consider yourself a loving and compassionate person? Then these things will help boost your confidence.

Lastly, if you feel terrible about the way you look, there’s a way to fix that: hit the gym. You might even meet someone there.

Hop on Online Dating 

Online dating might not be for everyone, but it has served some people well. It gives you a chance of meeting people you wouldn’t have thought of dating, and you don’t have to be tech-savvy to meet someone.

A good place to start is to show up as who you are.

There are also lots of dating sites targeted at people in their 50s. Some are free, and others are subscription-based. The bottom line is that there’s a high chance you might find someone just right for you online.

As long as you keep your expectations to a bare minimum, ensure that your profile picture is an accurate representation of you, and keep updating your profile, then there’s a high chance of meeting someone.

Be Resilient

Dating can be tough. You meet someone and connect with them, but they just don’t feel the same way about you. Ditto with you too.

However, you need to find it in yourself to accept it and move on. Don’t crumble into hopeless despair and mull over it for months. Accept that the universe will find you someone else, and they just weren’t meant for you.

It’s understanding that someone not liking you hurts your ego and sometimes affects your self-esteem, but you can’t match everyone else’s taste, so why not find someone else?

A couple dating in their 50s
A couple dating in their 50s

Explore and Exhaust Your Options

Don’t be in a hurry to settle with the first person who meets your standards; keep exploring for more options. 

At this point, don’t shut anything down. You might also find those younger than you interested, which is a big flex, but don’t write it off. See where it’s going to end up without shutting it off at the first trial.

Remember, there’s always someone better than the one you choose to settle for. Find the right person for you, and the best way to do so is to go slowly.

Take Up a New Hobby

It could be a cooking class, a book club, skiing, or a yoga class. The point is, taking up a new hobby also helps you put yourself out there, and it makes you feel like you’re part of a community.

You can connect with like-minded people, and it’s even better and quite easier to start a conversation with someone who shares the same passion for the things you love. Trust that there’s nothing better than hitting it off with someone you already know.


Your 50s are the perfect time to travel and have more exciting encounters. It doesn’t have to be a big trip out of the continent; it could be just as simple as exploring another town.

You never know who you might meet through travel. Aside from the fact that this opens you up to meeting more people, it also helps you live the life you’ve always wanted to live.

Again, it could be a great way to tell the next person who comes along where you last traveled, so traveling always comes in handy.

Bedroom Tips

Sex is important for any relationship to thrive, but ensure you stay protected in the bedroom. 

Also, don’t rush into it. Most people decide to have sex after the first date, but if you want to wait until the relationship becomes serious, then by all means do what’s comfortable for you.

Secondly, discuss this with your partner beforehand to make sure you’re on the same page. Also, if there’s anything they need to know and vice versa, be upfront about it. If there’s surgery, let them know before you two are in bed.

Lastly, don’t be coaxed into something you aren’t comfortable doing in bed.

Tell Your Friends and Family About it

If it’s serious, tell your support network about it. Even before you start dating, feed them in, but know when to be discreet about some things.

If you have kids who are unsupportive of your decisions, try to make them understand and listen to their side of the story. 

It’s important to tell your support network about it, but in the end, remember that your opinions and choices outweigh theirs. Never let anyone dictate to you how you should live your life.

A woman in her 50s telling her family about her plans to go out on a date
A woman in her 50s telling her family about her plans to go out on a date

Stay safe during dates

You’ll be going on a lot of dates, but make sure your safety is a top priority. Tell people where you’re headed, and if you aren’t feeling it, don’t feel compelled to stay.

Ensure your dates are in public spaces. Keep an eye out, and don’t give anyone the chance to take advantage of you. 

Also, as this isn’t limited to going on physical dates, stay safe online too. If there’s anyone who seems fishy and asks you for private details, report them. There’s always a bad experience, but the most important thing is that you come out in one piece.

Don’t hold back on saying No 

It could have taken you a while to meet this person, but if they don’t pass the vibe check, let them go.

Don’t protect anyone’s feelings. Be real and honest. They’ll appreciate it, and if they don’t, that’s not your problem, but don’t continue the dates if you aren’t feeling it anymore. 

Remember that this isn’t your ex-spouse, and you aren’t trying to save your marriage or protect your kids, you’re allowed to leave when you want.

Save Up Deep Conversations for later

In your 50s, you probably have lots of great and terrible dating experiences, but don’t be tempted to bond over them.

If your date asks, what happened in your last marriage? Say something nice about it. Your first date is like an interview, and it’s more of a data-collection phase. 

As long as you wouldn’t tell a potential employer you’re homeless, which is why you need the job, keep every private detail to yourself.

But why shouldn’t you bond over shared trauma? For starters, this isn’t a therapy session. You’re on this date to have a nice time.

Secondly, that doesn’t give you a chance to showcase how amazing you are. If you go on about past trauma, how would you talk about the kids you raised? How does yoga help you thrive, or anything else that makes you seem amazing?

Don’t Beg Anyone To Stay

You might like this person, but don’t grovel for their attention or for them to stay in your life.

If they want to leave after some point where they’ve made you feel special, then let them walk away. Although this is much easier in theory than it is in practice, not chasing anyone will solve a lot of your dating problems.

Believe that the universe will bring in someone new, and just say, “Thank you. Next!”


Age is nothing but an illusion. You can have the best love at age 20 and the greatest love in your 60s.

The most important thing is not to let your age stop you from doing things you would like to do. Yes, it’s going to be stressful, but is it going to be a wonderful experience? Then go get it.

Take it from Dating in Your 50s for Dummies: “Even if your walk is creaky and health difficulties are taking a toll on you, you’re not the only one with those issues.” 

As long as your heart is still functioning, there’s always someone out there for you because there’s never an age limit on matters of the heart. Go find that someone!

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Over the years, Stephanie has had her fair share of dating experiences. While some turned out great, others weren't so great. She believes that relationships are meant to be fun, exciting, and full of laughter. She wants to help men and women become confident, attractive, and successful in their romantic relationships.