50 Best Tips for Dating Over 50

With this advice, you'll be ready to get back out there in no time.

50 Best Tips for Dating Over 50
circle

Whether you’re recently divorced, widowed, or just haven’t found the right person yet, if you’re on the dating scene at the mid-life mark, you’re far from alone. According to Census data, more than a quarter of adults between the ages of 45 and 59 are single. In fact, there are 19.5 million unmarried Americans over 65.

However, while there may be plenty of fish in the sea, finding a real catch is easier said than done, especially if Nixon was still in office the last time you went on a first date. After all, “the dating world today is much different from the dating world even 20-plus years ago,” says life coach and licensed mental health counselor Dr. Jaime Kulaga, PhD. So, how can over-50 singles reenter the dating scene with confidence? Follow these tips for dating over 50, and you’ll find that special someone in no time.

1. Avoid internalizing rejections.

Whether you’ve been single for some time or have just gotten back on the dating scene after a long relationship, nobody likes feeling rejected. However, try not to take it personally when you don’t match with someone on a dating app or don’t hear from them again after a few flirty messages.

“Social media has improved dating, increasing the selection of people you can meet, but it has also posed some problems, too. One of those issues is the ease in rejecting people. In fact, on some platforms with a simple swipe to the left or right you can reject someone. But this rejection is not to be taken to heart,” says Kulaga. “With how many people you can meet online, think of rejection as a time saver as opposed to something that is wrong with you. Mister or Miss Right will come along, but you need to remain confident in who you are and open-minded to the people that come your way.”

asian couple with age difference dating over 50 Shutterstock

2. Expand your usual age limits.

Even if you’ve only dated people around your age in the past, why limit yourself now? While dating someone 10 or 20 years older or younger than you may have been a big deal in your 20s and 30s, you’ll likely realize that there isn’t that much of a difference between a mature 38-year-old and a 58-year-old, or even between a 50- and 70-something.

3. Ease into talking about sensitive subjects.

“Many fifty-somethings have built business and careers, are putting children through college and have even faced some health issues. But, on the first few dates with someone, it is not appropriate to focus on how much money they have in the bank and if they have health issues,” says Kulaga. “The first few dates should be getting to know each other’s personality, a little about their family, likes, a few dislikes, and fun life experiences. If date one jumps right to the serious and tough parts of life that even take a toll on the strongest couples, you may be weeding out (or they may be weeding out) some really amazing people to have fun with.”

4. Don’t be afraid to make your needs known.

Just because you’re not 22 anymore doesn’t mean you have to accept any kind of relationship that’s offered to you. If you’re over 50 and still want to play the field, or you’re looking for someone who shares a passion for traveling instead of spending nights in, it’s your prerogative to be honest about those wishes. Don’t compromise and find yourself in a relationship you don’t really want.

older woman outside dating over 50 Shutterstock

5. Embrace your age.

“Feel confident and sexy as opposed to finding ways to hide your age or lie about it. At some point, your age is going to come forward anyway—don’t lie about it today and then have to find ways to come forward with the truth later after you really like someone,” says Kulaga. “Talk about fun life experiences you have had and the goals you still have. Show your age and wisdom in fun, exciting ways that make people want to be a part of your journey.”

6. Listen attentively.

If you haven’t been on a date in some time, it may be hard to contain your excitement, meaning you end up talking more than listening. However, if you’re eager to land a second date, make sure you’re actively listening to the person you’re with—feeling heard goes a long way toward building trust.

7. Don’t expect things to be the same as when you were 20.

Dating isn’t necessarily the formal affair it was when you were younger, so don’t assume that you need to get your best suit ready, buy flowers, or get your hair done just to grab a cup of coffee with someone. Similarly, now that you’re older, don’t expect that things will get physical as fast as they did when you were younger.

8. Use photos on your online dating profile that reflect how you look currently.

While it may be tempting to obscure your lines and wrinkles by using a filter or by posting an antique image or far-off photo, there are plenty of people out there eager to date people who look like you—just the way you are today.

9. Send a few flirty texts.

Who says that a little digital flirtation is out of the question just because you’re over 50? While we’re not suggesting you send anything explicit to your date, a text reminding them that you can’t wait to see them again can go a long way.

older woman on computer ways we're unhealthy Shutterstock

10. Ask someone out—even if you’ve never done it before.

Even if asking someone out has never crossed your mind before, why not give it a try? While it takes a little bravery the first time, once you get a “yes,” you’ll have the confidence you need to do it again.

11. Try an age-specific dating site.

Don’t want your online profile to get lost in a sea of 20-somethings on your average dating site? Try an age-specific one instead. Sites like OurTime or SilverSingles make it easy to find someone who isn’t just fine with your age, but is specifically looking for someone your age.

12. Don’t get hung up on your past relationships.

A painful divorce or the 30 happy years you spent together before your spouse’s death may weigh heavily on your mind, but that doesn’t mean stuff like that is appropriate first date fodder. When in doubt, save the talk of your past relationships for later down the line.

13. Master a skillful compliment.

No matter what your age, everyone loves a thoughtful compliment. To ensure that your flattery isn’t misconstrued, try to make your initial compliments about your date’s personality or physical features from the neck up, like “You have such a winning smile” or, “I just love your sense of humor.” You’re aiming for charming, not creepy.

40 compliments dating over 50 Shutterstock

14. Ask a friend to introduce you.

Don’t feel ready to brave the online dating scene? Ask a friend to set you up. By the time you’re in your 50s, your friends likely know some other folks who are dating and also want to avoid downloading Tinder.

15. Put together some new outfits.

If you don’t feel good about the way you look, you’re going to be preoccupied when you go on a date. “Taking an absence from the dating world may have you feeling out of touch, insignificant, or flat out old. Nothing is sexier than confidence, so make sure you take the time to refresh your wardrobe, practice yoga, or work out,” says Maria Sullivan, dating expert and vice president of Dating.com. “Do whatever it takes to boost your self-esteem,”

16. Get some advice from friends who’ve started dating again.

Have your friends found love after 50? Ask them for tips!

“If you have children or younger friends you feel comfortable talking to about dating, get their input. You’ll be surprised at what kind of advice they have to give. You may notice that dating culture today is much more different than what you’re used to, and these loved ones can be great resources and confidence boosters,” says Sullivan.

17. Get to know each other before meeting in person.

Just because someone is interested in meeting you doesn’t mean you need to schedule an in-person date immediately. “Jumping straight back into dating after a long break may be weird at first. Test the waters by starting conversations with multiple people,” suggests Sullivan. “Once you feel you’ve found your groove, you can take the next step and meet for coffee or dinner.”

18. Go Dutch.

Even if you’re used to one party paying for dates, for some older people on fixed incomes, buying more than one meal or movie ticket simply isn’t in their budget. Offering to split costs takes some of the pressure off your date and allows you to sidestep some of those confining gender norms.

paying restaurant bill dating over 50 Shutterstock

19. Be patient (on dating apps).

Just because you don’t instantly find your inbox flooded with messages from potential partners doesn’t mean there isn’t someone out there waiting to meet you. Even for people much younger than you, dating is still a process, so be patient with both yourself and your potential partners.

20. Never trash talk your ex.

Even if your ex left you with a mountain of debt or some deep-rooted trust issues, do your best not to trash talk them to your early dates. While the end of your last relationship is bound to come up at some point if you keep seeing someone, if you say malicious things about your ex, your date might peg you as an unkind or cruel person and be less-than-eager to go out again.

21. Respond to messages in a timely manner.

Even if you’re not the most tech-savvy person, it pays to follow some basic etiquette rules when online dating, including responding to messages in a timely manner. While it may not seem like much time to you, the online dating world moves fast. So if you haven’t written back to someone in a few days, they’ll likely assume you’re not interested.

22. Look up your prospective dates online before meeting.

Before you agree to meet someone you met online, look them up first. Even a cursory Google search can bring up everything from their work information to their mug shot. Always better to be safe than sorry!

23. Talk yourself up online.

You may not feel as confident dating at 50 as you did at 25, but that doesn’t mean you should let that show on your dating profile. While nobody wants to a braggart, portraying yourself as the happy, fulfilled person you are can go a long way when you’re looking to meet someone new.

older man smiling outdoors

24. Don’t divulge any private or sensitive information.

So you met Mr. or Miss Right online—and now they’re asking you to deposit a check for them before you can meet in person. If any of your potential partners are asking you about sensitive issues early on in your relationship, like your finances or medical history, that’s a major red flag and a sign you should shut things down.

25. Have your first date somewhere public.

Your safety is paramount when it comes to dating at any age, so don’t agree to have your early dates at your home. Meet somewhere public for your first few dates and get to know the person you’re seeing before showing them your place or going to theirs.

26. Let someone know where you’ll be going.

If you’re meeting someone for the first time, play it safe and let a friend or family member know where you’ll be. At the very least, they can come rescue you if your date just isn’t a good fit.

27. Try a new hobby.

Having a hard time meeting new people? Try out a new hobby. Join a gym, take a pottery class, or hit up the dog park with your canine companion. These are all great ways to meet people who share your interests.

28. Practice your flirting IRL.

If you feel like your flirting skills are a bit rusty, try practicing on someone first. That doesn’t mean asking out the guy who took your order at Starbucks and told you to have a nice day. But you can—and should—test out a few compliments or smiling at a cute stranger to help boost your confidence and prepare you for the real thing.

older woman on beach dating over 50 Shutterstock

29. Take more solo adventures.

Being alone and being lonely don’t have to be synonymous. If you want to expand your romantic horizons, try taking a solo vacation, going to museums by yourself, or just exploring the town or city you live in on your own. You never know who you might meet!

30. Make eye contact.

You don’t have to play coy with every new person you meet. Make sure you’re giving good eye contact to whoever you’re on a date with—it’ll make them feel heard, respected, and more eager to learn about you, as well.

31. Don’t push yourself to do things you don’t enjoy.

While it’s not a bad idea to try new things if you’re looking to meet people, don’t force yourself to do activities you already know you don’t like. If you’ve tried archery, speed-dating, or marathon training and found that they weren’t good fits for you, pushing yourself to continue doing them will only make you miserable—and likely to meet people who don’t share your interests.

32. Don’t put all your eggs in one basket.

Who says you have to only date one person at a time just because you’re over 50? Not every date is going to be a great match, so feel free to cast a wide net. There’s no reason to feel guilty about going out with more than one person at a time before things get serious.

older male couple dating over 50 Shutterstock

33. Try dating outside your “type.”

Even if you’ve always had a particular type, don’t be afraid to try something new when you’re back on the dating scene over 50. Just because you’ve only dated white collar professionals doesn’t mean you won’t have just as much fun with someone working in a trade. And when it comes to physical appearance, dating someone who doesn’t look like your exes can be an exciting adventure in its own right.

34. Don’t try to sound too young on your dating profile.

You’re over 50—so why are you trying to talk like a teen? Peppering your dating profile with millennial or Gen Z catch phrases will only make you seem out of touch.

35. Be honest about why your past relationships didn’t work.

Once you’re in a relationship with someone, don’t be shy about revealing why your past relationships didn’t go the distance. While it’s best not to be outright unkind about your ex, revealing that you had different priorities in terms of your family or your career can help you and your new partner determine if you can see your relationship lasting.

36. Listen to those gut instincts.

If you’ve gotten a bad vibe from your date, don’t brush it off. Those gut instincts are there to protect you, so if something feels off, don’t feel bad about ending things.

older man younger dating over 50 Shutterstock/Akhenaton Images

37. Don’t assume that younger or older people who are interested in you have an agenda.

While it may seem a bit strange at first to have someone 20 years your junior or senior ask you out, don’t assume that they have ulterior motives in doing so. Just because you’ve never dated outside your age range before doesn’t mean that every younger person who wants to be with you is after your money, nor does it mean that someone older has a problem dating people their own age.

38. Protect yourself.

Just because you’re over 50 doesn’t mean you can throw caution to the wind when it comes to your sexual health. While getting pregnant might not be as much of a concern as it was when you were younger, that doesn’t mean it’s not possible—and all the STIs that were around when you were dating in your teens and 20s are still around, too. So make sure you’re using protection if you choose to get intimate.

39. Don’t assume that marriage and kids are off the table.

Even if you haven’t gotten married or had kids by 50, there’s no reason to rule them out entirely. There are plenty of couples who tie the knot or have kids later in life. If those things are important to you, don’t be shy about making that known when you start getting serious with someone.

40. Allow yourself to have fun.

That said, there’s no reason to feel like your relationships have to be serious just because you’re getting older. If you want to have a few casual flings or if you never see yourself getting married, that’s more than fine—just be honest about these things with the people you’re dating.

Older Couple dating over 50 Shutterstock

41. Try not to compare your new relationship with your previous ones.

Whether you think your former spouse is a virtual saint or a monster, it never pays to compare your current relationship to your old one. Every relationship is different, and telling your new partner the ways they’re better than your ex—or cataloging the things they don’t do that your ex always did—will only make them feel like they can never measure up.

42. Cast expectations aside.

In practice, dating after 50 can be very different than it was earlier in life. Health issues, complicated families, and different wants and needs can make dating feel like a totally different ballgame than it was in your 20s and 30s. So try to cast those expectations aside once you put yourself out there again.

43. Don’t be surprised if you get a little giddy.

Those butterflies in your stomach? That impulse to check your phone to see if they’ve texted? All totally normal. Just because you’re older doesn’t mean you shouldn’t be just as excited about meeting someone great as you were in high school.

44. Don’t immediately introduce them to friends and family.

You may be excited to meet that aforementioned someone great, but don’t assume that every relationship is going to be a lasting one. It can be awkward to feel like you’re pushing your date into in your inner circle, so wait until you’re certain you’re on the same page about your relationship before having him or her meet your family and friends.

older woman smiling dating over 50 Shutterstock

45. Don’t downplay your accomplishments.

Playing dumb or making light of your achievements is no way to start a relationship. If you’re proud of your career, your hobbies, or the children you’ve raised, don’t feel obligated to say otherwise to impress your date. Anyone worth seeing again will think it’s exciting to discover what you’re passionate about.

46. Don’t ditch your standards.

Just because you’re older doesn’t mean you have to give up your standards when it comes to dating. You’re still a catch, and the people you go out with should be, too. So, that person who suggested you drop a few pounds, belittled your career, or acted like they were doing you a favor by dating you can just slink back off to whatever hole they crawled out of.

47. Ask them out again if you had a good time.

Even if you didn’t make the first move, that doesn’t mean you can’t make the second one! If you had a great time with someone, go ahead and drop “So when can I see you again?” into the conversation.

48. Get back in touch the day after your date.

Playing games isn’t cute at 20 and it’s definitely not a good look at 50. If you had a good time on your date, let them know! There’s no need to stick to that ancient “three-day rule.”

woman working on smartphone and laptop computer outside dating over 50 Shutterstock

49. Bu don’t feel obligated to go on a second date if the first didn’t work out.

Didn’t feel a connection with your date? Don’t waste your time—or theirs—by going on a second one. No matter what your age, there are plenty of fish in the sea, and there’s someone out there who you will find that connection with.

50. Enjoy the journey.

The most important thing to remember when you’re dating over 50? This is supposed to be fun, so try to enjoy yourself!

“Each date, especially early on, should be focused on getting to know each other and having a good time,” says Kulaga. “Enjoy each opportunity to go out and smile, laugh, and just have fun!” And for more amazing dating advice, here are 40 Reasons Why Being Single in Your 40s is the Greatest Thing Ever.

To discover more amazing secrets about living your best life, click here to follow us on Instagram!

Filed Under
Best Life
Live smarter, look better,​ and live your life to the absolute fullest.
Get Our Newsletter Every Day!
Enter your email address to get the best tips and advice.
close modal
close modal
GET YOUR FREE GIFT
SUBSCRIBE