How To Date When You’re Over 50

Dating again in your 50s is often an entirely different kettle of fish to dating in your 20s, 30s, or even 40s. Most people will have been married before, and may potentially be divorced or even widowed.

A survey by the Today Show in America found that only 18% of women will admit to dating in their 50s. It can be a tricky world to navigate, but fear not – it can certainly be done, and can be lots of fun. Sheryl Crow and Sandra Bullock are just two of the fabulous, single women in their 50s. And if they can put themselves out there at 50, why can’t we? There are lots of great dating sites for over 50s, and more ways than ever to meet new people, so now might be a better time than ever before to get yourself out there…

So we spoke to dating expert and matchmaker at dating agency Mutual Attraction Caroline Brearley, and dating over 50s expert Lisa Copeland (, to get their expert opinion on just how to date when you’re over 50…

Caroline said that anxieties can plague 50+ women when it comes to dating. What are some of the most common anxieties she’s found women over 50 have when it comes to dating? “That there aren’t any eligible single men left (there are!), that no men will be interested in them, that they aren’t in shape, and a fear of rejection. They want to meet someone but also want to stay in their cosy safe spot – their comfort zone.” Lisa agrees, stating that, “You think you’re coming to the table as less than perfect, but we forget how awesome we are at 50.”

But despite these worries, Caroline has said that she found that; “Women who are 50+ are much more open and
honest. They don’t try and hide what they’re looking for, but they’re
more willing to compromise. We find in this age group men and women are more likely to go on
second and third dates with someone, as they’re more
willing to take the time to get to know someone.” Perhaps life experience really can help contribute to a better dating life…

So what is the best way to go about dating when you’re over 50? Read on to find out…

If you haven’t dated for ages, say yes to new opportunities – but be realistic

Caroline says, “We at Mutual Attraction find that women who haven’t really dated before (because they’ve been married for years previously, for example) are either totally petrified at the thought of it, incredibly excited, or more commonly a combination of both.”

“I would encourage women who haven’t dated before to just really embrace it, to say yes to meeting new people and new opportunities, and to enjoy it. I do try to ensure that women I coach are realistic though, by telling them that they aren’t going to feel a connection with everyone they meet, and it might take a fair bit of dating before they meet the right one for them – but that’s not necessarily a bad thing. Dating can be incredibly empowering.”

Don’t take knock backs personally

Easier said than done of course! Caroline says “Those who have been dating for a whilst know that not everyone will respond to their message on a dating website, or that their date might not always want to see them again after their first date. It can be a real confidence knocker. But you won’t be everyone’s cup of tea, and that’s okay. Hold your head high, and move forward – there are plenty more lovely people to meet.”

Try out a dating site

They’re an easy, fun, and safe way of meeting new people – dating sites are the perfect way to get yourself back out there. Try Woman and Home’s dating website, Woman and Home Plus One to meet people your age, websites like eHarmony, specialist countryside dating site Muddy Matches, or specialist 50+ site, Fifty Dating. Lisa agrees that “Online dating sites are the best places to get started, as there are a huge range of men on them.”

Make an effort for a date – or what’s the point? 

Caroline says, “Every woman has their own character and personality that shines through in
their clothes and accessorizes. If you aren’t willing to put in some effort to your dating life, then it could be a sign that it’s not the right time for you to be dating at the moment.”

Lisa also recommends having three go-to outfits that you feel great in, saying “Before your date, you don’t want to be dumping and going through your whole closet! Really dress up, with a dress and heels if you want to – why not?”

Make sure to take time to reflect on your life before you start dating

Lisa admits that it’s important to find your own passions again, saying that “Men love women who are really passionate and enthusiastic about something.” Caroline also agrees that it’s important to take time for you before dating again, “It’s really important for a woman to know where she’s at, where she’s heading and the type of person she wants to meet to enjoy life with before she gets on the dating train – especially if she’s previously been married for decades.”

Think about what has worked and what hasn’t in past relationships, to figure out what you really want

“We encourage our clients be open to meeting a diverse mix of people and to throw away their supposed ‘list'”, Caroline says. “Many things that are on a woman’s ‘must have’ list for a partner are things that actually aren’t that important in the grand scheme of things and things that, should an amazing guy come along, they would be more than willing to compromise on.”

“If you have more than 3 things on your non-negotiable list then go back and look at them each in turn and answer ‘Why is this so important to me?’ Often what was important to us years ago isn’t as important now. Don’t miss out on meeting wonderful people for the sake of thinking he has to be tall!”

Lisa agrees, stating that it’s also key to take a look at your previous patterns of men. She says to be careful with this, “As we can often re-attract the same guy”, which isn’t necessarily always a good thing.

Keep your first dates light and breezy – and don’t go into too much detail

Lisa tells us – “The only purpose of a first date is to get to a second. You won’t know if he’s the one, you’ll just be able to work out if you have chemistry with him.”

Caroline says, “First dates are really just a chance to see whether you would like to get to know one another more, so focus on having a laugh together instead. Dating in your 50s is unlike your 20s. You are bound to have a past. You may have a family, responsibilities, have travelled the world, been divorced – who knows! Anyone dating in their 50s is going to know that you have a past, but there’s no need to divulge everything just yet.”

Ask trusted friends to each set you up with one person they know

“You’ll be surprised how willing people are to play Cilla! It’s difficult to meet people these days, which seems crazy given how we seem to be more connected than ever,” Caroline told us.

“But if you would prefer to meet people organically, a great place to start is to ask friends to play matchmaker. Plus, having someone to
talk to and share your dating experiences with, can be the biggest
confidence boost of all. And a big glass of wine at the end of the night can always heal a bad date…”

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