Dating In Your 50s – Things You Should Know

Single Life | | , Copy Editor & Writer
Updated On: July 16, 2022
dating in your 50s

The common assumption that floats around is that dating in your 50s is certainly more challenging than say, dating in your 20s. In your 20s, the dating pool is wider, the stigma associated is less and one, in general, feels more freedom when it comes to pursuing others. Over time, that scenario changes and by the time you’re 50, it’s a wildly different dating world for you.

But even if the dating world doesn’t resemble what you’ve experienced before, it doesn’t mean that single 50-year-olds are still not out and about trying to find someone for themselves. Dating in your 50s as a woman is a challenge but by no means, an anomaly.

To really help you see that even more, read the following account about how a woman helps her best friend to start dating at 50.

Trying To Get My Friend To Start Dating At 50

“Where do I even begin to find a boyfriend for her?” I wailed (typed in), staring at my phone. And clicked on the ‘staring eyes’ emoji several times, to emphasize my point. I was on a ‘battling the post-prandial slump’ chat with my lovely, old friend and inspirator (inspirer? The second sounds like a medical device of some sort.)

When I get bogged down with my virtual red penning, I pick up my phone to text whichever of my friends know how to deal with my mood of the moment. Today was Lola’s turn.

She’s a feisty, fiery, creative polymath of a woman I’ve known for a few years now. She’s an ‘older’ woman, let’s say on the ‘wrong’ side of 50. She’s been happily single for many years, divorced from the father of her sons years ago. Her children are now independent — the last one even has one foot outside of the nest. Apart from regular skirmishes to get the ex to pay his fair dues in alimony, Lola has overcome serious health issues, a temporary estrangement from her own family, and a hurricane several months ago when she lost valuable property.

Related Reading: How To Manifest Love In Your Life – 5 Proven Ways

Not that any of the strain shows in her attitude. Far from it. She’s who I go to for cheering up, or when I need to vent. And she’s always got an unrelentingly positive response to the questions, complaints, or seemingly unsolvable problems I throw at her. She’s literally ‘been there, done that’ in so many fields, that sometimes I simply shrug and roll my eyes when she airily says, “Oh, I did that in 198- or 199-, and then this happened…”

She always challenges me to try new things, because she says everyone should learn one new life skill every year, to keep dementia away. So what was she asking me to do this time that caused me to wail?

Finding a partner in your 50s is no joke, and that’s why she needed me

She needs my help finding a boyfriend for herself. Emphatically NOT a husband, but a good boyfriend. Someone single, about 55 but definitely over 50…and with good teeth, she added for good measure. “Why are the teeth important?” I asked, dazed. “Oh, I don’t know, it’s just my current mood,” she dismissed the non sequitur, and pushed on, “So what are you going to do about it? C’mon now. Help me find a boyfriend!”

I gingerly suggested that perhaps she could be happy with a BOB (Battery Operated Boyfriend)? I know where to find those in SF, I offered, temptingly since that is the only easier option when you’re dating at 50. “Nah! It has to be an actual man. It’s time to find a boyfriend who loves me. I want one.”

finding a partner in your 50s
How am I supposed to find a boyfriend at 50 for her?

To find her a boyfriend is not my cup of tea

If you really know me, you’d know what an impossible and paradoxical task this is. I’m almost the antithesis of a matchmaker. I’ve been known to ask point-blank “Why?” when told about a successful young woman getting married. So you see the irony.

I admit I’m very handy with my thumbs and forefingers when it comes to locating craft supplies, thanks to Google and Amazon. Living in SF gives me the confidence to sally forth armed with nothing but my iPhone and a credit card, and explore the back alleys of the stores, digging up bag-making supplies and tools. But to help my bestie find herself a boyfriend? How? Where? Why?

But I don’t know any single men, 55 or anyone else dating at 50. How do I find a boyfriend for her? Unless you count my 17-year-old nephew. Or my 2-year-old cat (and let’s just say, he no longer has the goods to deliver, er, the goods).

I’ve never even looked at my friend lists and considered who’s single. Did I even know any single men? Nope. Single men dating at 50? Oh, even more challenging. So what is the best way to find a boyfriend? I thought I’d ask some of my other friends.

I asked a couple of my girlfriends for help: “Do you know of single eligible men in the right age bracket?” A friend who loves to rile me up sent me a picture of a man who, she said, would be wonderful husband material. “I said ‘No Husbands!’” I repeated, only to have her text me a looooong list of his qualities. Just in case there had been a miscommunication, I pointed out that I wanted a boyfriend, NOT a husband. She cackled, “I just like having pointless discussions.”

Related Reading: 18 Dating Tips To Find The Right Person

The position is still open if you are dating in your 50s too

I flailed about for many days until suddenly it occurred to me that here at Bonobology I might just have the perfect weapon to hunt down that 55-year-old or so boyfriend with good teeth, who are smart enough not to be intimidated by a strong independent woman. Who can match wits with her and keep her mentally engaged as well.

Where can an older single woman go to find a friend? Again, no husbands need to apply. Do you know of anyone who might work? Are you one yourself? Do write in and help me in my quest of how to find a new boyfriend for my best friend. I need to defend my “Finder Extraordinaire” title.

Tips On Dating In Your 50s

Finding a partner in your 50s is going to be a lot of work, we won’t lie to you. As mentioned before, the dating world has not only progressed, but it has also changed. With the flurry of online dating apps, hook-up culture, polyamorous relationships and so on, don’t go into this expecting an old-school romance that will sweep you off your feet.

The romance is still very much out there, alive and kicking, don’t get us wrong. But there are some things you need to prepare for. Especially, if you’re thinking about seeing someone who might be younger than you. Lucky for you, we have a few tips ready for you already. So without further ado, let’s get right into this dating over 50 advice.

1. Leave the inhibitions around your age at the door

Whether you are looking for a partner who is your age, older than you, or is even younger than you, the only way you can constructively start dating in your 50s is if you stop worrying about your age! If you’re joining a dating app, do NOT lie about your age, your occupation or any of those things. If you’re a mom or a grandma, be proud to say it loud. In fact, why not crack a joke about it in your bio? Something along the lines of, “I have three huge kids but on most days, I still feel like I’m the youngest of all!”

Related Reading: How To Keep A Guy Interested? 13 Ways To Keep Him Engaged

2. Do a little push and pull

Maybe back when you were younger, it was okay and acceptable to fixate on one person or see one person at a time. However, things have changed tremendously now. Just because you went on one nice date, does not mean that you have to ask them out again tomorrow. Space out your dates, play a little game of push and pull, and don’t make yourself too readily available for them.

Moreover, this is your time to explore and experiment. So take your time, meeting and getting to know multiple people! Go out on lots of dates before you finally zero down on the one.

3. When dating after 50, try to say ‘Yes’ to things

This dating over 50 advice is one that we hope you will not forget. You might be feeling lost in this new dating world and you’re probably a little wary of how it works. But the only way to make the most of things is to start saying the word ‘Yes’ when an opportunity comes your way.

A speed dating event for singles over 50? Yes. A double date set up by your friend? Yes. A new red dress, the type that you haven’t worn since you were 28? Hell, yes.

4. Don’t bring up your past relationships too much

As a 55-year-old woman or maybe more, we realize that you’ve dated a lot and have even been married once or twice. That’s cool, we get it, and by no means is it a dealbreaker. But when you ask us, “How to date in your 50s?”, we have to give you this important piece of information. The more you ruminate over your past relationships on your dates, the more unattractive you might seem.

As a woman in her 50s, you want to seem independent, like someone who has seen the world enough and is now living life on her own terms. Isn’t that the best thing about age? So make sure you’re not coming off as a broody, old woman who can’t go to bed without kissing a photograph of her ex-husband goodnight. That will NOT work in your favor.

We hope that this advice about dating in your 50s as a woman was helpful to you. Remember, be confident in your own skin, know what you want, and go out there and own it. This is common advice for all ladies out there no matter how old you are!


1. How likely is it to find love after 50?

Finding love at 50 is really not impossible. Only because mainstream culture has always emphasized young love, we are unaware of people’s stories of dating at 50 or finding a boyfriend or girlfriend at a later time in their lives. It is absolutely likely and much more common than you think.

2. Is 50 too old to date?

Absolutely not and do not let anybody tell you otherwise. If you want to find a boyfriend at 50, you can totally do it! Tell your friends to hook you up or join a dating app. There are many ways you can ace finding love after 50. There is no age to tell you when you can or cannot date or fall for someone.

3. Is dating harder in your 50s?

It might feel like it because perhaps you haven’t dated in a while, but that is not necessarily true.

4. What does a 50-year-old man find attractive?

A man likes a high-value woman. Check out the traits of a high-value woman here.

5. Is it too late to find love in your 50s?

You can find love at 20, at 40, at 50, or even at 80!

When You Find “The One” You Just Know It In Your Heart

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