Dating After 50: A Woman’s Guide To Finding Love

Dating after 50 can be a challenge; I mean, dating at any age has its ups and downs.

Maybe you’re newly single, you’re out of practice when it comes to dating, or you’ve never really dated much at all. The way we date has changed significantly over the past ten years, and online dating can be intimidating from the outset.

According to a recent survey, only 18% of single people in their 50s were dating, while 40% were considering it but taking no action. More than 40% of people didn’t believe anyone was out there to date, 30% don’t know where to start, and 30% say they find the experience too stressful.

But dating after 50 can be wonderful, maybe even better than ever before. Most older women are more comfortable in their skin, know what they want (and don’t want), and are confident in who they are and what they bring to the table. These are all benefits when it comes to dating.

So, if you’re single and ready to meet an amazing man, I wrote this post for you.

Here’s my guide for women dating after 50 who are serious about finding true love.

1. Practice self-acceptance.

If you find yourself dating again after 50, after being in a relationship for a long time, your confidence may have taken a knock. This is normal. You haven’t dated in forever, your body may have changed during this time, and the dating scene is different now.

Before you start dating again, it’s important to practice self-acceptance, which means accepting and loving yourself exactly the way you are today and being patient and kind. Because the truth is, we all have our flaws. But when you feel good on the inside, this will radiate on the outside and automatically make you look more attractive.

2. What can you learn from your past relationships?

If your previous relationship broke down, take time to reflect on this, as well as your other relationships.

Why didn’t they work out? Usually, both partners are responsible.

What can you learn from these relationships, and are there any common patterns?

What have you learned about yourself in the process?

There are so many valuable lessons in our past relationships, and if you are open to receiving these lessons, you’ll then be able to avoid repeating the same mistakes.

This is what growth looks like.

3. Dating after 50: Figure out who you are and what you want now.

If you were married or in a relationship for a long time, dating after 50 requires you to figure out who you are now and what you want. Doing this will help you find a man who matches your love vision and save you wasting time on the wrong guys.

Many women (and men) lose a sense of self after being married for a long time—it’s easy for this to happen, especially if you devoted most of your time and energy to raising a family.

So, think about who you are now.

What kind of life do you want to live?

What are the qualities you’re looking for in a man, and why are these important to you?

Know what your deal breakers are, but leave some wiggle room when it comes to those nice to have things that aren’t mandatory.

For example, if he smokes like a chimney, and you cannot stand the smell of smoke, that’s a deal-breaker. But if you’d like a man who’s a good cook and he manages to burn toast, it’s not the biggest deal. I mean, if he ticks all the essential boxes, you can live with that, right?

4. The sexiest thing you can wear is confidence.

Men like confident women. Chances are, you’re attracted to confident men too. Confidence is sexy, period.

Being confident dating after 50 can be challenging because your physical appearance has changed over the past 30 years. You can’t compete with 20-year-old women, and you don’t need to either.

If a man in his 50s is interested in chasing 20-year-olds, let him do his thing. Forget those guys, and look for a man who’s looking for more than just arm candy.

To build your confidence, focus on your best qualities and all the reasons why a man would be lucky to date you. Be yourself, be genuine and be honest. Many men will find the maturity and experience you have attractive. So instead of focusing on the negatives, look at all the benefits of dating after 50.

5. Give yourself a makeover.

One of the best ways to boost your confidence is to give yourself a makeover.

Clear your wardrobe out, and invest in some new flattering pieces that will make you feel and look fabulous. If you’re not sure where to start, opt for classic, high-quality pieces: a black dress, a tailored coat, a great pair of jeans – things you’ll wear and love for years. You could also enlist the help of a stylish friend or relative or even hire a stylist.

You might feel the urge to go for a dramatic change in appearance, like cutting your hair or going from brunette to blond. If you’re feeling it, go for it! This will help you release any stuck energy you’ve been holding onto and make way for the new.

Are you heading on a date for the first time in a while? Treat yourself and get your hair and makeup done by a professional.

6. Take care of yourself.

The Eastern Ontario Research Institute conducted a study and found people who exercise twice a week over ten weeks feel more competent and have a higher body image than those who don’t.

Exercise releases endorphins and will instantly make you feel good. On top of that, this is a great way to look after your physical and mental health. When you do this, you’re showing yourself love, and it helps boost your energy and mood.

Plus, gyms and exercise classes are a brilliant way to connect with new people.

7. Lean on your loved ones.

Dating after 50 can feel a little strange at first. You might feel self-conscious about it, especially if you have children who are old enough to know what’s going on.

When it comes to your kids, honesty is the best policy, but avoid introducing them to anyone until you’re serious about this person.

Having a strong support network around you is vital during this time. You’ll want a friend you can call for a pep talk before you go on that first date, someone you can share dating stories with over coffee, and people you can enjoy spending time with who love and care about you.

8. Put yourself out there (even when you don’t feel like it).

When it seems like there are no good men left, ask yourself if that’s the case, or are you closing yourself off from meeting them?

Dating at any age requires openness and vulnerability. You have to get out of your comfort zone, meet new people, and start going on dates.

Love will not magically happen—it’s on you to put yourself out there and make it happen.

You may have gotten into bad habits over the years, but today is the day to break them. Start saying yes to things, be more adventurous, try new hobbies, sign up to a dating app.

Go on nights out, go to restaurants, head to bookstores and libraries, take golf lessons, head to a cooking class, join a hiking group, ask your friends to set you up.

Men are everywhere.

You’ll create a fuller life for yourself and increase your chances of meeting someone fantastic.

9. Look at dating as a way to meet interesting new people.

I don’t need to tell you that not every date will set your soul on fire or give you butterflies. But it’s easy to forget this truth and end up seeing dating as a chore.

What if you took a different approach to dating?

What if you started looking at it as a way to meet someone new, from a completely different walk of life? Instead of viewing it as an interview, what if you relaxed a little and focused on enjoying this person’s company and having fun?

If you focus on having fun, you’ll take the pressure off yourself and are much more likely to have a good time, regardless of whether it’s a textbook “good” date or not.

10. Dating after 50: Reawaken your sexuality.

Many women find themselves in marriages and relationships where their sexual needs aren’t met. And even if you had a great sex life, a breakup can often have a knock on effect on your sexuality.

Ask yourself, do you feel sexy?

If not, when was the last time you did feel sexy?

Just because you’re in your 50s, it doesn’t mean this part of your life is over. You deserve to feel sexy every day. And somewhere inside of you, that desire still exists; you’ve just let it fall into the shadows.

Feeling sexy doesn’t happen instantly—it takes time and requires consistent effort.

A couple of great ways to reawaken your sexuality include wearing things that make you feel sexy, soaking in a bubble bath, exploring your body, trying a sex toy, or reading an erotic novel.

11. Use a dating site for over-50s.

Online dating may be intimidating after 50, but it’s a great way to meet single men who are also looking to find love. There are also dating sites specifically aimed at mature men and women, and these are a great place to start.

If you’re a little challenged when it comes to technology, ask a friend or relative to help you get set up and take a nice photo of you.

And remember to see this as an adventure and a way to connect with new people. Not everyone will be your soul mate, but every date will teach you something about yourself and bring you one step closer to finding true love.

12. Take the pressure off the date.

If you’re nervous about going on a first date, my advice is to keep things casual.

Don’t go for dinner on date number one, because it’ll make the event feel more formal and serious. Go for coffee or a drink or a walk, and see how things go. You can’t predict whether the conversation will flow or not until you’re face to face.

If you’re not feeling, you can cut the date short without any friction.

13. Focus on companionship first.

Another great way to combat first date nerves is to focus on companionship first instead of looking for your future husband.

Finding someone you enjoy spending time with and feel comfortable with is vital. Of course, you want to be physically attracted to him, and your personalities should compliment each other.

But focusing on friendship will help you relax and focus on finding someone you genuinely enjoy spending time with. If and when things start heating up, then you can shift your mindset.

14. Flirt like a grown-up.

You’re never too old to flirt. But what do you need to know to charm a guy?

Keep your body language open and positive, smile (if you’re genuinely having a good time), and make eye contact with him often. Embrace your femininity, use his first name, compliment him, and don’t be afraid to touch him lightly if you’re feeling it.

If you feel out of practice, brush up on your flirting skills with a random guy you don’t find attractive. Keep doing this to build your confidence up. The more you do it, the easier it will become.

15. Make sure the conversation on a date is balanced.

Making sure the conversation is balanced on a date can be challenging. You want to make sure you’re both opening up and sharing about yourself but also taking turns to listen to each other actively.

If you don’t learn enough about each other on the first date, it’s difficult to progress to date number two. Plus, it’s never attractive when someone steamrolls a conversation and doesn’t give anybody else a chance.

So, if he’s talking too much, segue into a new topic that allows you to speak. And if he’s not opening up enough, try and ask open-ended questions that need more than a yes or no answer.

16. Dating after 50: Let him be a man.

You’re a strong, confident, independent woman who can take care of herself. That’s a beautiful thing. But at a biological level, men are wired to want to protect you and be your “hero.” It doesn’t mean they see you as helpless or weak; it’s because he sees you as valuable and worth protecting.

So when you’re on a date, let him be a man. Let him make sure you’re safe and protected and looked after. The feminine side of you might enjoy being supported by his masculine energy.

17. Don’t assume you’re exclusive.

Dating after 50 doesn’t automatically mean every guy is looking to settle down and be exclusive with one woman. Some guys will be keeping their options open, and it’s vital you do this too.

That means go on lots of dates with different guys. See what you like and what you don’t, and decide whether they match your love vision. This will help you build your experience and confidence up and figure out what you want.

Don’t assume you’re exclusive until you’ve sat down and had the talk, and you’re both on the same page. If you’re on different pages, walk away and move on.

18. Go at your own pace.

Just because you’re older, it doesn’t mean you need to rush to find someone and settle down. Let go of the pressure to be coupled up or married again. There is no timeline for anything. Let things happen organically.

Real love takes time to evolve, so resist the urge to speed things up, even if you like someone. Giving yourself time will help you make rational decisions and build a healthy foundation for your relationship to grow.

19. Put your safety first.

If you’re dating after 50, you may be out of practice with the ins and outs of staying safe while meeting new people.

Don’t give your phone number out too soon to men you meet online. There’s no problem keeping things on the app or website until you know you can trust this person.

When it comes to meeting up, always make sure you do it in a public place, and tell someone where you’re going. Never leave your drink or bag unattended. And don’t agree to anyone picking you up or dropping you back home when you’ve only just met.

You can never be too careful!

20. Don’t have sex until you’re ready.

This is just as true when dating after 50 as it was 30 years ago. You’d be surprised how many mature, intelligent and competent women end up having sex before they’re ready and waking up the next morning with regrets.

If you’re not ready to have a conversation about safe sex with this man, then you’re probably not ready to have sex. And if he doesn’t respect this, then show him the door.

When you’re both ready, make sure you’re protected and that you voice your needs and wants in the bedroom. Any man who cares about you will want to make you happy and make sure you get yours.

21. Don’t give up!

Finally, perhaps the most crucial strategy for dating after 50 is to keep going, even when things aren’t going your way.

You might go on several dates and find all the men are terrible matches for you and nothing you imagined them to be. Maybe you end up liking someone who doesn’t feel the same way.

This is all part of dating. Don’t take it personally. And don’t ever give up on finding love—there is a great man out there looking for an incredible woman like you.

Conclusion: That’s everything you need to know about dating after 50.

I hope this article has shown you that although dating may be different after 50, your odds of finding love are just as good as they were 20 years ago.

You’re never too old to start dating again.

Are you a mature woman who’s looking to get back out there and find love? Let me know what your biggest challenges and success stories are in the comments below.