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What are the rules for dating after 50?

While there are no fundamental rules for dating—no one size fits all—there are certain things you can do to be both successful and respectful when dating after 50!

Maria Montgomery
· 11 min read

What are the rules for dating after 50?: Your questions answered

  • What do men in their 50s want in a woman?

    Compatibility. If you want a more in-depth answer, have a look at another article I wrote.

  • Finding love after 50: how to begin, where to go, what to do?

    Begin by loving yourself and creating a life you love. Take time to exercise, eat well, partake in activities you enjoy, fuel your passions, and come to terms with who you are and who you are not. Fill your diary with YOU; with the things you want to do.

    Then, join a dating site (you can read about how to write an online dating profile here) and look for activities near you where you can meet others. Expand your social circle. Eventually, this will lead to meeting more singles. From there, be open to go on dates, realising that it might take a while to find the one, and some dates will be horrible. Don’t take it personally. Enjoy the journey and laugh at the mishaps.

    I have written a more in-depth article about how to find love after 50 here.

  • What are the best dating sites for older people?

    All the big sites and apps are suitable. These include Tinder, Bumble, Match, eHarmony, Parship and Elite Singles. Both Tinder and Bumble are free dating sites.

    You can also try Silver Singles, OurTime, and Lumen (a free dating site for over 50s).

    For (virtual) speed dating, check out Original Dating.

    If you’re asking, “is Tinder OK for over 50s?” the answer is “yes.” There aren’t going to be as many people over 50 on there as there are people in their 20s and 30s. That doesn’t mean you should discount it. Use it together with other apps. And be clear about what you’re after on there, be it casual dating, hookups, love, or friendship.

  • What are the chances of finding love after 50?

    Huge. Massive. Humungous. If you know what you want, you’re open (emotionally), and you relax, having faith it will happen, it will. Do take time to brush up on your social and relationship skills, too. Read books about communication, relationships and sex. Learn. Grow. Create fantastic relationships with the people you meet.

  • Dating over 50—when to kiss?

    When it feels right. Everyone has a different idea about dating etiquette these days. You can cheekily ask someone their opinion before you make any attempts at kissing them! Then, wait for the mood to be right. You don’t want to jump someone! If anything, learn to read body language.

  • What are the signs s/he is falling for you?

    Do they genuinely care about how you are doing? Do they check in often? Do they talk about a future with you in it? Do they outright say they are interested? If so, chances are they like you, but the best way to find out is to ask. Do you see this going anywhere? Don’t ask them this on the first date, but if you’ve been dating for some time, then it’s fair to ask. From the beginning, establish open communication instead of making assumptions about what the other person is thinking and feeling.

    What percentage of 50 year-olds are single?

    Does it matter? There are enough singles for you to find love, that’s for sure!

  • What do older guys like in bed? What do older women like in bed?

    Everyone’s different. Compatibility is the name of the game. Most people also look for partners who are willing to talk about what they wish to experience together

    That said, everyone looks for appreciation—they want to feel desired. Compliment them as a person, compliment their body, compliment their skills. In bed, tell them when they do something you enjoy. Show them how much you desire them.

    As a general rule though, everyone want a partner who is willing to set time aside to create a great love life—prepare romantic dates, send naughty texts, create new experiences, and take their time to get you in the mood.

I always cringe when I hear people speaking about the so-called rules of dating. No one size fits all, so what one person considers correct, another considers incorrect. That said, there is some etiquette any respectable person should follow. Additionally, some other things will likely make your dating experience that much more enjoyable…and successful! Let’s have a look at those things, shall we?

Be upfront about what you’re looking for

Since the invention of online dating, people have become fed up with beating around the bush. After realising some people have, let’s say, unclear intentions, people have become pretty good at asking upfront what the person they meet is looking for.

Maybe it becomes even more critical when looking for love after 50—you’re at an age where you no longer feel you have the patience for false pretences. You want to know what you’re in for from the get-go. And it’s a wise choice. Why go on a date with someone looking for something casual when you’re looking for a relationship, and vice versa?

Be polite

Dating in your 50s as a man or woman usually means you’ve been through enough in life to appreciate kindness. In your 20s, you might have fallen for bravado or physical attraction alone. In your 50s, you look for signs a man or a woman is kind, considerate and on the same path in life as you are. Politeness is often the first sign of integrity, though, of course, you have to dig a little deeper to see if it’s truly there.

No ghosting

This should be the dating etiquette for any age, but when you reach 50, it’s time to grow up enough so you can communicate. If you no longer wish to see someone, tell them. If you met them online and after a first date neither one of you makes contact, then fair enough. After that, if you no longer wish to see them, you say so.

If it’s only been about three dates (and no sex), then it’s OK to text someone to say you don’t want to continue seeing them. If it’s been more, then you’re better off calling them or seeing them in person.

If, after a first or second date, you realise it’s someone you’d rather be friends with (i.e. you do wish to stay in touch), then say so. Send them a text right away letting them know you appreciated meeting them, but you’re getting a friendship vibe. You'd love to get to know them better, sincerely, but as a friend. Then suggest another meeting. Some people may get offended, but then that’s on them! 

Get clear on what you’re looking for

Most people are surprised when they find their perfect match isn’t exactly the kind of person they had in mind. It’s always quite the surprise when the love of your life walks in!

But most of those people had ideas about what a good relationship looks like and how they want to spend their life.

To avoid ending up with someone who isn’t right for you, start thinking about what a good relationship looks like to you. What are your needs? What are you willing to do for your partner? And where do you want to take your life? Once you know these things, also consider how to communicate them. Your dates won’t be mind readers. 

In short, you need to be able to communicate your wants and needs, as well as elicit your dates. Do you think, after that, that you’re a fit?  

Overcome mental blocks

Looking for love while at the same time thinking "people are cheaters," "everyone dumps me," "I will never meet the kind of person I want to date," is going to get in your way. We have all been hurt in love—starting with our parents and peers not treating us exactly as we wanted at all times. Look at what you honestly think about love, and then establish what you’d like to think. After all, not everyone is a cheat, and your perfect match will not dump you—they’ll celebrate you. It’s not about being “the best” but finding the puzzle piece that fits you. 

Understand boundaries

Most people in their 50s have an established lifestyle. Maybe they’ve been through a divorce, and there have been some changes, but they still have set habits. Possibly they have children. Letting someone else into their life means finding new habits and finding someone respectful of the life they’re already leading. Maybe they aren’t looking for another parental figure for their children. Perhaps they want to take things slow. Perhaps they aren’t looking for someone to move in right away.

To be successful at dating, learn to ask about what people want—find out about their boundaries. As you get closer, things may change, but don’t count on it. 

Stay clear of your past disappointments

If you go on a date with someone who tells you how awful all the other men/women out there are, it’s a big turnoff. And if they keep going on about how bad their past relationships were and how it was all because of their partners, it’s a big warning signal.

If you’re 50 or older, chances are you’ve had some disappointments in love. Hopefully, you’ve learned from them, taken responsibility for your part in them, and realised that some people out there don’t understand communication and relationships, and others have bad personalities. That’s life. Being bitter about it and stuck complaining about it is your choice, though. 

In short, one of the rules of dating after 50 is that you show that you’ve learned things and become a better person thanks to your previous dating experiences. At least it’s a rule if you want to impress potential dates.

State things in the positive

If you want a lot of “likes” on your online dating profile, state things in the positive. Speak about what you enjoy in life and what you’re looking for in a partner. Avoid talking about what you don’t want and what you aren’t looking for. If you aren’t looking to date someone dishonest, state that you’re looking for someone honest.

A positive outlook is one of the most attractive personality traits out there. And once you get to know someone, if you’re talking about something difficult you’ve been through, or are going through, state it in the positive. “I’m currently going through a difficult divorce, which has taught me to treasure my friends so much more. They’ve truly been there for me. And I’ve discovered I can have a new, beautiful life outside my marriage. Five years ago, I could never have imagined that.”

Reframing things in that way won’t just help you when dating; it will help you with your life at large. You will look for opportunities as opposed to lamenting misfortunes. We are all faced with adversities—what matters is how we handle them.

Be confident

No one is confident about every area of their life. However, people tend to look for confidence in men and women over 50. They want to see that their life experience has made them more comfortable in their own skin and that they dare to live life on their own terms. It’s one of the most attractive traits in people over 50.

The funny thing is, if you become OK with not being confident about one thing or another, you end up being confident about it. It’s when you’re not OK with having insecurity that it takes hold of you. Once you no longer care about it, it no longer stops you from being confident. You can just say, “Listen, I’m insecure when it comes to x, and I want to overcome it.” In short, you can be confident about being unconfident.

Stay away from the "I never thought…."

Instead of talking about how you never thought you’d be single at a certain age, talk about the positive aspects of dating again. Are you suddenly allowed to experience dates you never did in your 20s? Do you get to do the wild things you feared back then? Or the more mellow stuff you never took the time for back in the day? Are you allowed to dress to impress and get butterflies in your belly when meeting a lovely date? Are you having fun laughing till you cry when a date goes tits up? Well then, maybe being single isn’t so bad after all.

Never ask, "Why is a nice person like you single?" 

Answers will likely be: 

  • My ex died.
  • My ex cheated on me. Clearly, I had to learn a lesson when choosing partners.
  • My ex dumped me.
  • My last relationship didn’t pan out, so we broke up.
  • I’ve been looking for love for a while, but something seems to have been holding me back.
  • If I knew, I wouldn’t be single.

How do you think those answers make someone feel?

Be OK with failure

I always say that your dating life should be like a romantic comedy—you have to find the humour. You will meet men or women who are terribly dull, absolutely not compatible with you, or (in your opinion) downright strange. You might have to endure one hour of not knowing what to say when on a first date, which is why a first date should always be short and preferably include an activity. You may even have to endure the company of someone who makes your skin crawl.

Expect these things. Don’t feel downtrodden when they happen. They’re part of the journey. Laugh about them.

Don’t create great expectations

If you meet someone online, be sure to know that they will be different in real life. Even if you video chat with someone, the real-life person will be somewhat different. This is why you should meet someone as soon as possible. A quick coffee is usually a better way to assess your compatibility than ten hours of online chatting.

That said, there’s nothing wrong with finding out a few things about someone before meeting them. If you feel you need to chat to someone for a little while, then, by all means, do so. Just beware that you don’t waste too much time doing so and creating expectations that might never be met.

Keep first dates interesting

If you meet someone online, you don’t know what to expect when you meet them in real life. The image we create of someone never quite matches the real person. Therefore, keep the first date interesting—partake in an activity that gives you something to talk about.

If you can, do something like bowling, visiting a farmer’s market, playing ping-pong, or going for a walk along the river. This will keep you both busy and give you something to talk about.

If you don’t fancy that, a quick coffee or drink, where you have something arranged so you can’t stay long, is ideal. The time limit ensures things don’t have to get weird when you run out of things to say.

Encourage the other person

Some people find first dates difficult. And while we’re all learning from our mistakes, coming out of a nasty divorce, ending a long relationship, or having been through a string of unfortunate relationships, it’s not easy. So, encourage the other person. Give compliments freely. If they run out of things to say, speak. If you can, think of ways to encourage them in different ways.

Receiving heartfelt compliments usually makes a person open up to you. And they will remember you fondly, even if you don’t end up together.

Listen

The art of listening is one we think everyone should have learned by 50, right?! But have they? No.

Google active listening and do your best to engage in it.

Maria Montgomery

Maria Montgomery

Maria has lived in seven different countries around the globe. While trained as an actor, director and producer, mainly she’s been paid for putting her words to pieces of paper. She also has an entrepreneurial streak and is the owner of Magique and That Woman Is A Woman Productions. Her blog, Confessions of a Dizzy Blonde, offers her life learnings, sprinkled with a large dose of humour…and sex!