Dating over 50: an expert guide to finding midlife love

So you’re single again at 50-plus? Congratulations, you’re right on trend along with a record number of baby boomers.

We know that dating again after a long-term relationship can feel daunting. In fact, according to research from dating site Ourtime, and Debrett’s, the authority on modern etiquette, a huge 60% of 50+ Brits feel less confident dating now than when they were younger.

So that is why we’ve called on the expertise of the UK’s top over 50s dating experts to help you navigate this tricky new world and maximise your chances…

The ‘old fashioned’ approach: meeting in everyday life

There are so many places you could potentially meet a new partner. Relationship coach Susan Quilliam suggests spending less time in ‘babbling brooks’ (places people go to chat but where dating is not the overt agenda, such as a neighbour’s party) and ‘stagnant pools’ (where you see the same people week-in week-out, such as evening classes).

Instead, look for ‘slow river’ activities such as walking groups, meet-ups (search online for events in your area) or dance classes, which deliver a stream of new people.

The ‘more modern’ way: older dating online

Choose a site that suits your interests or style so that you’re fishing in a place with the most like-minded people. Muddy Matches is great if you’re a country type, while My Single Friend and even My Lovely Parent will get you out of writing your own profile, as your friend or children do that for you.

MORE: Jojo Moyes Picks Her 5 Most Romantic Reads

There’s a dating site for almost every niche these days, including the over fifties (Our Time). Have a look at the other profiles on there and follow your gut instinct if it’s right for you.

The same goes for dating apps such as Tinder and Bumble, which are fast moving, fun and flirty – but also brutally superficial. Try them if you’re feeling brave, but since 83 percent of Tinder users are under 35, know they offer fairly slim pickings for anyone born before the Internet was invented.

Creating an online profile

Almost half of those in Debrett’s research (48%) admitted they struggle to write a positive online dating profile.

“I tell my clients, show don’t tell,” says midlife dating expert Rebecca Perkins, who met her own partner online when she was in her fifties.

Give a snapshot of your life that shows who you are. “That might mean describing a day on holiday in your favourite location, or a conversation you’ve had with your teenage son about whether you should go kitesurfing, anything that makes you stand out.”

However, it’s key to ensure that the photo is the right one – specifically, a recent one, so no one is left disappointed! Debrett’s suggests,  “Recent photographs, should be no more than a year old, when creating your profile. There’s no point trying to mislead your date if you ever hope to meet in person.” Another pro tip – “Make sure you’re the only person in your photographs – an innocent friend or family member could easily be misinterpreted as a former flame.”

Sitting photo

Ourtime dating expert Kate Taylor also recommends to “write your profile like you’re introducing yourself to someone at a party, keep things upbeat and avoid divulging health issues and innermost thoughts at this stage”.

Also, “Don’t be creepy, though: it’s far too early for come-ons or innuendo”. According to Debrett’s, a quarter (24%) of over 50s would be put off a potential date if they used too many emoji’s.

What to expect on a first date

First of all – when do you suggest a date if you started chatting online? Debrett’s found that one in five of us would wait at least ten messages before even suggesting meeting up.

However, Debrett’s suggests there’s no need to even wait that long. They say, “Once you’ve surpassed the five-message mark, it makes sense to take the initiative and propose a date. Tailor the date around a shared interest, like a visit to an exhibition.”

There’s also nothing wrong with suggesting a daytime coffee rather than an evening meal initially in case you want to make a quick escape. Though if you’ve been getting on really well chatting online, you might want to extend this to lunch.

The key thing is to let go of expectations, stop worrying about what might happen next, and just enjoy the date for its own sake. Try to stop thinking that you’re here to meet your next life partner; instead, that you’re here to have a nice chat and possibly make a connection.

Text etiquette

While ‘courting’ largely happens by text and email these days, Quilliam advises scheduling an old-fashioned phone call before you initially meet, and meeting within three weeks of the first message.

According to research, dragging out an email or text exchange will increase your chances of feeling disappointed when you do finally meet in the flesh.


There are no rules here. “A lot of men will be coming from long marriages where the sex has dried up and the can be a bit like teenage boys,” advises relationship therapist Andrew G Marshall. “Bit that doesn’t mean they’re only interested in sex.”

But there’s no need to feel alone if you’re feeling anxious. According to Debrett’s research, only 24% of over 50’s would have sex in the first week of dating.

You’re a grown-up, you decide and do whatever feels right – but don’t feel pressured.

And most importantly, enjoy your dating life!

Words: Sharon Walker and Amy Hunt

Most Popular