Dating In The 50s – 15 Tips To Do It Right

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Dating in the 50s can be an unnerving proposition for most people. Perhaps, you have been single for the better part of your adult life. Or maybe you spent the past few decades in a long-term, committed relationship. The days when you were active on the dating scene can seem like a distant memory.

The circumstance of your singlehood notwithstanding, entertaining the question of how to start dating in the 50s and put yourself out there can be daunting. But if you yearn for companionship, don’t let your inhibitions hold you back. Yes, there are challenges of dating in the 50s, but these needn’t become roadblocks in your quest to find companionship.

With the right approach, you can not only date successfully but also find true love in your 50s.

Dating In The 50s – 15 Tips To Do It Right

Want to start dating in the 50s but don’t know where to start? Perhaps, you’re a little skeptical about being rusty and out of sync with the rules of the dating game. Maybe you are even wary of the chances of finding love after 50 and don’t want to crash and burn. We hear you.

As long as you look at it as a way to reclaim control of your life, the balance begins to tip in your favor. With the right outlook and some handy dating in the 50s tips, you can turn this nerve-racking proposition into a thrilling adventure.

Here are 15 tips that will help you kickstart your journey to dating in the 50s on the right note:

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1. Know what you want

Have you been contemplating new relationships in your 50s? Are you looking to find true love in your 50s? Is your decision to date again an outcome for a quest for companionship? Or are you just in it to have a good time while it lasts? These are all valid reasons to get back on the dating scene. So, don’t dismiss them because you have been told, ‘Why bother dating after 50!’

That said, before you get back on the dating bandwagon, take some time to introspect about your goals. Understand why you want to do it in the first place. Knowing what you want from the experience can make the ride that much easier. When you know exactly what you want, you’ll seek it in the right places.

Related Reading: 12 Facts Of Older Woman Younger Man Relationships

2. Embrace online dating

The concept of looking for potential partners or true love in your 50s with a few swipes on a phone can seem alien to anyone other than the generation of digital natives. Considering the paradigm shift in the dating scene to the virtual space, this can undoubtedly be one of the most pressing challenges of dating in the 50s.

It helps to keep an open mind and embrace online dating because that’s where most opportunities are. If you’re serious about finding a partner, you simply cannot afford to give online dating in the 50s a pass.

Besides, there are a host of dating sites and apps that cater to singles over 50 – eHarmony, DatingOver50, Bumble, Match, Lumen, to name a few. Check these out and see which ones best align with your dating goals, and create profiles accordingly.

3. Invest in your dating profile

rules of dating after 50
Your dating profile has a lot of bearing on the kind of matches you attract

Once you’ve narrowed down the dating sites or apps that you want to sign up on, make sure you invest time and effort in writing your dating profile. Your profile picture and other photographs, bio, interests, hobbies and what you seek in a potential partner have a lot of bearing on your chances of matching with the right people.

Whether you’re dating in your 50s as a woman or a man, making sure your online dating profile is on point goes a long way in connecting with like-minded people. So, don’t skimp through this process.

If you are not sure how to go about it or your dating profile isn’t yielding the desired results, don’t hesitate to ask for help. Your friends who are already active on these dating sites or younger people in the family may be able to help you in choosing the right angles and filters for photos as well as crafting a succinct bio.

4. But don’t abandon the traditional approach to dating

Online dating in the 50s does not mean you have to swear off the good old-fashioned approach to find love and companionship. Given that there are not as many singles in that age bracket, and even fewer still try to date, you have to diversify your outreach to improve your chances of finding love after 50.

Ask your friends to set you up on dates. Pursue a new hobby or join a group of solo travelers, backpackers, bikers or surfers (depending on your interests). This will allow you to connect with like-minded people and find a connection with someone organically.

dating in the 50s infographic
How to ace dating in the 50s

Dating in the 50s is cool and can be a lot of fun when done the right way. So, don’t just fixate on the end result, enjoy the journey as well.

Related Reading: Older Man Younger Woman: 9 Reasons Why Dating With Age Gap Works

5. Rejection is inevitable

Knowing what to expect when dating in the 50s is essential to protect yourself from hurt and disappointment. Expecting to find an everlasting connection on the first date you go on would be somewhat naïve. In all likelihood, there will be more than a few misses along the way before you get a hit. This is especially true if you’re banking heavily on online dating in the 50s to find a partner.

Accept that rejection is an inevitable part of the parcel. Some dates will turn you down (maybe even ghost you) and some you will turn down. Don’t let these experiences bog you down or put you off dating.

The best way to take rejection in your stride is to embrace the ‘pineapple theory’ – some people cannot bear to have pineapple on their plate while others love it. The fruit remains the same, it is people’s taste for it that differs.

Similarly, some people may not like you as much as others. It’s all a matter of perceptions and preferences, and has got nothing to do with you.

Communication, image and etiquette coach, GeetArsh Kaur says, “Do not rush into things. Even if the first few dates with someone go extremely well, don’t presume that they want the same things as you do or start expecting a long-term partnership with them. Keep things simple and uncomplicated, and take it slow. This can help mitigate many challenges of dating in the 50s.”

6. Steer clear of comparisons

If you’re dating in your 50s after divorce or the loss of a partner, starting with a clean slate is unrealistic. This person has been an integral part of your life for years. Someone you loved dearly at one point and shared an intimate journey with.

It’s only natural that when you meet someone new, their actions or mannerisms may remind you of how similar or different they’re to your former partner or spouse. A fleeting thought or two on these lines is perfectly fine.

Likewise, even if you’ve chosen to stay single for the better part of your adult life, there may have been a relationship or two in the distant past that has sculpted your perception of romantic partnerships. You must try to actively rein in any tendency to assess your dates vis-à-vis your past relationships.

Remember that every person is unique. And new relationships in your 50s are not a replacement for old ones.

7. Research your dates

It is advisable to research your date after you connect online and before you both agree to take it forward in real life. A quick internet search can give you a sneak peek into their social media handles and other relevant online activities to help understand whether this person is genuine or not.

This is also important because there are romance scammers lurking in the virtual space, looking to trap unsuspecting people in their net and fleece them of their money. Be it dating in your 50s as a man or a woman, you must treat this step as non-negotiable.

The online dating space is fraught with fake profiles, catfishers, and romance scammers and tt’s better to err on the side of caution rather than end up with dashed hopes and an empty bank account.

8. Don’t carry your baggage to your dates

true love in your 50s
Go on dates with an open mind

Whether you’re dating in your 50s after divorce or a long-term relationship gone wrong or have been single all along, there is bound to be a lot of emotional baggage. Perhaps, you have developed trust issues or a tendency to be wary of emotional attachments.

While all of that is understandable, it’s not fair to judge someone new based on your past experiences. Now that you’ve made up your mind to give dating another chance, go on dates with an open mind.

Don’t overthink or overanalyze the other person’s words or actions. You may end up attaching meaning or drawing an inference that was never intended. Unless you learn to detach yourself from the baggage of the past, you won’t be able to embrace dating in full earnest.

Remember dating in the 50s is cool only as long as you open your heart and mind to the experience. If your inherent inhibitions stop you from going all the way, you may not be able to enjoy the experience to the fullest.

9. Be open to questions about the past

‘So, what made you want to date again?’ ‘How long have you been single?’ ‘Why didn’t your marriage work out?’ Questions on these lines are something you should expect when dating in the 50s.

The other person will be inquisitive about your life story and would want to understand where you’re coming from before taking things forward. Don’t take offense or begrudge them for it.

If you’re not ready to open up about the past or think that it doesn’t make for an appropriate first-date conversation, keep your answers brief. But don’t dodge or be vague in your responses. If your date asks you something that is too intimate or personal, you can politely steer the conversation away from the topic with a casual, “That’s a conversation for another time.” or “I’d like to tell you all about it, just not right now.”

GeetArsh says, “At the same time, be aware of boundaries, both your own and that of the other person. Know what topics to talk about, how to take a conversation forward and when to stop. A complete lack of boundaries can be put off.”

The simple rule of thumb should be to not ask your date anything you wouldn’t be comfortable talking about, if the situation was reversed.

10. Be honest

When you’re in your 50s, any potential date would be accepting of the fact that you come with some history, not-so-pleasant experiences and emotional triggers. If they are at the same stage of life as you, they’d too.

It’s best to take a candid and honest approach in letting them see you for who you are. Be clear about your dating goals and expectations as well as your circumstances.

Kids, ex-spouses, alimony battles, an ugly divorce, affairs, cheating – whatever it is that you may think can be viewed as a red flag must be laid bare as early on as possible. By doing so, you enable the other person to make an informed decision about whether or not they want to take things forward.

Speaking of the importance of honesty when dating in your 50s, GeetArsh says, “Do not flaunt unnecessarily or be a show-off. More often than not, the other person can see right through you, and needless to say, things won’t go too far. Be your authentic self. Don’t hide your vulnerabilities behind superficiality. Be who you are, and your chances of finding a real connection will improve dramatically.”

11. Confide in your loved ones about dating in 50s

online dating in 50s
Tell your family and friends that you want to get back on the dating scene

There is no reason to be self-conscious about your decision to start dating in the 50s. If your heart tells you that it is the right thing to do and you have no strings attached, your age shouldn’t be a deterrent.

But before you take the plunge, have a conversation with your loved ones about it. They may have questions about your decision to start dating again, and you must address them as honestly and candidly as possible.

Invite the family over for a meal, sit them down, and say, “I’ve decided to date again.” In all likelihood, their reaction would be far more favorable than the worst-case scenarios swarming your mind. In any case, it’s better to keep them in the loop right from the beginning rather than introduce them to your new partner over Christmas or Thanksgiving without any forewarning.

12. Weigh the pros and cons of age-gap relationships

Just because you’re in your 50s doesn’t necessarily mean that you will end up with someone in the same age bracket. You may end up connecting with and falling for a person much younger than you.

While there is nothing wrong with age-gap relationships, they do come with their unique set of challenges. Whether it’s the case of men over 50 dating someone in their 20s or older women attracted to younger men, you need to be mindful of the myriad complexities that can arise out of such relationship dynamics.

If both you and your potential partner are ready to embrace a few bumps along the way, follow your heart by all means.

13. Flirt your heart out

Just because you’re a certain age doesn’t mean that you cannot or shouldn’t flirt. On the contrary, you must bring on your flirting A-game to charm and win over potential romantic interests.

The secret to how to start dating in the 50s successfully lies in being able to flirt like a grown-up and leave a lasting impression on your dates. This means no cheesy pick-up lines or outlandish sexual overtures.

Instead focus more on using your body language, appearances, words and slight yet noticeable physical contact to make a move on your date and make your interest in them be known explicitly.

Don’t fixate on nitty-gritty like dating over 50 when to kiss or make a move on someone you’re interested in. If you sense that the attraction is mutual and the moment feels right, just take the plunge.

14. Know when to ask for a second date

dating in 50s tips
Give your date time to process the experience

So, you went on a date and had a great time. Should you suggest a second date at the end of the first? Or is it better to leave things open-ended with a casual ‘we should do this again sometime’?

The latter is always a safer bet. Your date may not have had the opportunity to process the experience and understand what they want next right when you’re saying your goodbyes. Suggesting a second date or asking them out upfront can be a little overwhelming.

Instead, let them know that you had a good time and would like to see them again. You can touch base a day or two later to ask how they felt about the date. If their response is favorable, swoop in with your second date suggestion.

15. Don’t be awkward about intimacy

In dating over 50 when to kiss, when to make sexual advances can all be very confusing. Except it doesn’t have to be if you go by the simple rule that you do it if and when you feel ready. And of course, your partner feels the same way too.

For instance, if things progress organically and you find yourself reaching for their lips or vice-versa, don’t get in over your head and hold yourself back on purpose. Similarly, if you’re making out and things progress to the next level, just go with the flow.

Crossing the threshold of being intimate with someone new can be riddled with inhibitions and awkwardness. But intimacy is an important part of any romantic relationship. If you want to forge a strong bond with your new partner, you have to be comfortable with the idea of being intimate with them.

What Are The Rules Of Dating After 50?

How to start dating in the 50s? What are the rules? What are the challenges of dating in the 50s? How does one overcome those challenges? Is there a set of dos and don’ts that one needs to be mindful of? These questions – and many others – can weigh on your mind as you brace yourself to get back on the dating scene after a long hiatus.

how to start dating in 50s
Understand how to approach dating in your 50s to improve your chances of finding a partner

Here are some general guidelines that can help you operate within the acceptable norms of dating after 50:

  • Work on yourself before dating in the 50s: Before you start dating in your 50s after a divorce, breakup, losing a spouse or having been single for years, spend some time focusing on yourself. Fix what’s broken before you set out in quest of love
  • Be honest: Be honest about your past as well as your future relationship expectations. Don’t lie or hide things just for the sake of impressing someone
  • Enjoy yourself: Have fun on dates and don’t be solely fixated on the idea of true love in your 50s
  • Watch out for red flags: Don’t ignore any red flags in a potential partner out of the fear that you may end up alone
  • Ease into the dating game: Try to keep the conversations as light and breezy as possible during the early stages of dating
  • Strike a balance: Don’t pursue a new relationship at the cost of all other relationships in your life, including the one with yourself
  • Slow and steady: Take things forward at a pace that you’re both comfortable with
  • Set boundaries: Set physical and emotional boundaries in consultation with the person you’re dating
  • Listen well: Focus on your dates to make them feel valued and appreciated. Be a good listener
  • Open up: Let your new partner in and open up to them about your experiences
  • Don’t bond over pain: Find common ground but don’t bond over shared pain of the past
  • Talk about the future: Discuss how the two families will blend in if you decide to take the relationship forward
  • Embrace intimacy: Don’t be conscious about your body
  • Groom yourself: But do put in some effort into your appearances when you’re dating someone new
  • Don’t go all in too soon: Go on at least three dates before you make up your mind about someone
  • Shun the guilt: Don’t feel guilty about finding love and happiness again

Dating in the 50s shouldn’t feel like a chore. If you set your expectations right and give it your best shot, your odds of finding a companion for the rest of your days can improve exponentially.


1. What percentage of 50-year-olds are single?

According to statistical data, in the US, about 27% of men and 29% of women in the 50 to 64 years age bracket are single. Above 65, these numbers are 21% and 49%, respectively.

2. What do men in their 50s want in a woman?

The dating or relationship goals can vary from person to person and not be generalized based on gender or age. While some men in their 50s want to give love and companionship another chance, others may just be looking for flings and having a good time.

3. Why is dating so hard in your 50s?

Dating in your 50s is hard because of a whole host of reasons. First and foremost, there are fewer single people in the age bracket and fewer still are looking to date. Besides, your own baggage and past relationship experiences can make it hard to embrace the idea of dating again.

4. Is 50 considered old for dating?

Not really, as they say, 50 is the new 30. With more and more people investing in their health and fitness, living fuller and more wholesome lives, 50 is not too old to be dating.

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