13 Things To Know About Dating As An Older Woman



It can be daunting when you’re dating as an older woman in your 40s, 50s, 60s, and beyond. You’ve found yourself newly single, for whatever reason, but dating has probably changed a LOT since you last did it. Online dating seems terrifying, the dating pool appears to have run bone dry, and you’re much more set in your ways at this point, which can make the whole prospect of finding a good match seem near impossible.

Over a third of Baby Boomers are not married, and of those who have been (or are), there are higher rates of separation and divorce. It’s no secret that we’re all living a lot longer these days, which has also led to a consistent increase in the divorce rate for those over 50. Those stats can be a total downer if you take them too seriously, so we’re just going to park these right here for the rest of this article.

Stats aside, I want you to know that while dating might be different as an older woman, it can still be exhilarating. I’ve helped countless women in their 40s, 50s, and 60s find love—even when they thought they were too late to the dating party—and I’m confident that you can find love too.

So, if you’re feeling a little overwhelmed and need some solid dating tips before you jump back in, keep reading.

Dating as an older woman? Here’s what you need to know

1. This journey will be uncomfortable

The longer you’re in a relationship with someone, the more comfortable you’re likely to feel. So when that security blanket gets ripped away from you, it can feel as shocking as being thrown into an ice bath. You’re waaaaaay out of your comfort zone. Life has dramatically changed. It feels like you’re beginning again from scratch.

But here’s the deal: this isn’t a bad thing. In fact, it’s a beautiful thing. The best things happen when we push out of our comfort zone. Discomfort = growth. So remind yourself of that every time you feel lost or fearful of what lies ahead. Trust that you’re on this journey for a reason. Embrace feeling uncomfortable.

2. Learn to love yourself inside & out

Self-confidence and self-love are things I know all women struggle with at all ages (us guys have our fair share of those hang-ups too, but there’s less pressure on us). Sometimes women reach that middle stage of their life and feel more comfortable in their skin than ever before, while others struggle to accept the natural changes their body has gone through. If you’re in the latter, do your best to forget about how you “should” look (WTF does that mean anyway?!). Practice self-acceptance for the way you are today.

By all means, start moving your body more—if you want to. Get a makeover—if you want to. Have a complete overhaul of your wardrobe—if you want to. But turn down the volume on your inner critic and start recognizing your value. Think about all of your gifts, your talents, and the amazing qualities and quirks that make you, you. Little Love Step #1 is all about building your sexy confidence before you start dating so that you can begin positioning yourself as a high-value woman (because you are one, whether you realize it yet or not).

3. Stop thinking you’re going to die alone

woman on sofa

Yes, dating might have changed since you last did it. Yes, lots of men are happily married with kids. And yes, you might have to go on some crummy dates with some guys that don’t meet your love vision.

But stop focusing on the negatives. We attract what we think about most into our world. So instead of focusing on what you don’t want and all that could go wrong, start thinking about what you do want and everything that could go right.

Anyway, the reality is we’re ALL going to die alone. We come into this world alone, and we leave this world alone. That’s life. There’s nothing to fear about it.

This is your much-needed reminder that you are worthy of a remarkable man, and you will find your way to him in time.

4. Let go of the stigma of being single

We live in an extraordinary time where single people (particularly women) are met with sympathy and pity, while those coupled up or married are put on a pedestal by default. Statements like, “I can’t believe you’re single” are thrown around with good intentions, but would we ever say the equivalent to our married friends?

We automatically assume that one is better than the other, but it’s not. And even though your intentions are to date and eventually find a long-term relationship, please remember there is NOTHING wrong with being single!

“Being single isn’t wrong. Sit with that a while. Because when you do, singlehood starts proving its worth to you, starts showing you all the little pleasurable pockets you haven’t been able to see before. If you give a happy, valid singlehood a chance, I think you’ll like it. I think you’ll give fewer bad actors in the dating space the chance to negatively impact how you feel, too.”

Shani Silver, author of A Single Revolution.

5. Make friends with other single women

dating as an older woman

When you’re dating as an older woman, one of the things that can be the biggest obstacle to your success is surrounding yourself with happy couples. I don’t mean you have to ditch all your married friends, but if you don’t have any single girlfriends, it’s time to make some.

You’re in a different place in your life now. The last thing you want is to feel ostracised by all your coupled-up girlfriends. So make a point of spending plenty of time with other singletons. People who want to join you on speed dating nights and wing-woman you at the bar and swap crazy dating stories.

Join a local singles group, pick up some new hobbies, or join one of the many apps designed to help people make new friends.

6. Dating has probably changed a lot since you last did it

dating as an older woman

Hello, online dating.

Everyone has an opinion on it.

Love it or hate it, I think it’s safe to say that it’s here to stay. According to Katie Sheppard, director of relationships at Match.com, online dating is now the second most common way couples meet across the UK after being introduced by mutual friends or family.

My advice when it comes to online dating is to choose a site or app focused on helping single people find long-term relationships instead of something casual (unless that’s what you want). A few of the ones I recommend to my Love Accelerator clients are Bumble, Hinge, Zoosk, and Match.com.

I know many people want to meet their partner in real life and have a meet-cute moment, but waiting for love to come and find you is a mistake. You’ve got to take the initiative and start taking conscious steps towards what you want.

If you need a little help when it comes to the tech side of getting your profile set up, ask a friend or family member to help you out. And remember to be vigilant and watch out for potential scams—there’s a lot of people online who are not who they say they are.

7. Accept that you might have “baggage”

mother and daughter

Nobody gets to their 40s, 50s, or 60s without a healthy amount of baggage piled up. Exes, divorces, kids, grandkids, health issues… whatever you’ve got going on does not phase me in the slightest. And here’s what I want you to wrap your head around—all the men you’re going to be dating will have their fair share of baggage too.

So quit being embarrassed by it or feeling like it’s going to hold you back from finding love. That’s all in your head.

I’m not too fond of the term baggage anyway. I think of it as living life. If you feel like you’ve got a ton of baggage, that means you’ve done a lot of living, and that’s a beautiful thing. Accept who you are and where you stand today. Don’t be afraid to be upfront about your circumstances from the beginning when dating someone new. The right person won’t be put off by “baggage.”

8. But with that comes plenty of experience

Following on from what I just said in the previous point, by the time you reach that middle phase of your life, you’ve racked up a ton of experience. Think about how far you’ve come over the past year, five years, or the last decade. You’re smarter, stronger, and wiser.

One of the common fears about dating as an older woman is that you’ll be competing with younger, more “attractive” women in their 20s and 30s. While those women might look more youthful, you can still radiate youth in the way you behave. Get in touch with your playful, childish side and commit to having fun while getting to know new people. After all, age is no more than the number of candles on our birthday cake each year.

Focus on all you have to offer someone, and you’ll quickly realize there’s a lot.

9. Practice your flirting game

If it has been a hot minute since you last dated, then it’s normal to feel like you’ve forgotten how to flirt. But like anything, it can be learned, and learning how to flirt again can be incredibly empowering and liberating.

Here are some simple tips to get you started:

  • Pay attention to your body language. For example, make eye contact with men you’re interested in and smile (these two things alone can make a world of difference).
  • Don’t be afraid to compliment him on something.
  • Joke around, tease him (gently), and laugh with him.

If you feel self-conscious or nervous about flirting with men you’re attracted to, start practicing with men you’re not attracted to. Flirt with the guy at the grocery store, the guy who makes your coffee each morning, or the guy who’s fixing your car at the garage.

The more you flirt, the more natural it will start to feel, and the more fun it will be!

10. Don’t limit yourself

When you’re dating as an older woman, it’s essential that you don’t close yourself off to new possibilities or be so specific in the kind of man you’re looking for that no one comes close. Of course, set the bar high and have your boundaries and values, but at the same time, don’t rule anything out before you’ve given it a fair chance.

You might have a limited or fixed idea of what the perfect man or relationship looks like. For example, maybe you want someone between a specific age range or someone who has kids because you also have kids. But what if there’s a guy out there who matches your love vision (Little Love Step #2) but is two years younger than your ideal age? Or what if there’s a guy who is perfect for you in every other way, but he doesn’t have kids?

This is why I encourage you to be open to all kinds of men from all walks of life. Because who knows who you’ll end up building a deep connection with?

11. Don’t settle for less than you deserve

This relates nicely to the last point. While it will absolutely benefit you not to close any doors until you’ve explored what’s behind them, it’s equally important not to lower your standards or settle for someone who doesn’t treat you well.

You’ve gotten to where you are right now without a man, and you’re doing fine, right? You don’t need a man, but you’d like one. There’s a big difference there. So remind yourself that you don’t need anyone when you’re dating. You don’t need to settle for the first guy who walks into your lie out of fear of not meeting anyone else. Take things slowly, and don’t commit to anything that doesn’t feel right.

12. Get comfortable making the first move

dating as an older woman

This one applies to all women, no matter what age bracket you fall into. If there’s a guy you’re interested in, it’s okay to be the one to strike up a conversation or ask him out for a drink. Similarly, when you’re dating someone, it’s okay to ask questions about where you stand, where the relationship is heading, and say that you’re ready to be exclusive (if you are).

You don’t have to leave everything up to the man. Some guys are genuinely shy. Others might think you’re the most beautiful woman EVER, but be too intimidated to ask you out. So if you’re feeling it, go for it.

13. Let’s talk about SEX

Finally, on my list of things to know about dating as an older woman is to be safe in the bedroom. I don’t want to sound like an old man, but I’m prepared to wear that label if it means you’re taking care of yourself as you start dipping your toes back into the sea of dating.

Just because you’ve already been through menopause, it doesn’t mean you can forget about protection! Regardless of whether you’re 20 or 50, it’s important to use contraception and make sure you trust your partner enough before taking your relationship to that next phase.

So, to recap: enjoy having sex, protect yourself, and respect your boundaries.


I hope this article has helped calm your nerves (a little), stoked the fire within you, and left you feeling excited about this next chapter of your life. Who knows who you’ll meet, where you’ll go, and where this journey will take you over the coming weeks, months, and years?

Remember, there’s no pressure to start dating again if you’re not ready yet. So take your time. Make sure you’re at peace within and prepared to welcome in someone new.

What are your biggest fears or reservations about dating as an older woman? Let me know in the comments below.

dating as an older woman

PS. If you’re ready to start making men pursue you for love, then join me on this free webinar to discover the 3 steps to building emotional attraction – Register here to get started (it’s 100% free).