4 tips on dating as you get older


It can be quite a shock to the system, being in the dating game again decades after you were “single and ready to mingle”.

After years of the comfortable companionship that marriage can provide, finding yourself suddenly single and out there trying to meet people can be nerve-racking and leave you feeling vulnerable and unsure of yourself. Whether you’re single again due to death or divorce, dating later in life has unique challenges.

A reader recently shared her feelings about her first date with a man she’d been chatting to on WhatsApp for a while but hadn’t met face-to-face. And many women who’ve started dating again after years of being part of a couple can relate to her lament.

“As I nervously tuck my hair behind my ear, I wonder how I got here. I used to be happily married – or so I thought – until I discovered my husband had met someone else,” she says.

“Now I’m having to relearn dating – to meet men in a world that’s so different to the one I lived in when I was young and pretty.

“A world where you meet someone on the internet, and no longer through mutual friends or at a reputable establishment. A world where you get to know each other through WhatsApp messages and hear the other person’s voice for the first time only once you finally get around to meeting each other face-to-face over coffee

“And suddenly I’m faced with someone I barely know because he doesn’t resemble his profile pic. I fake a smile and take a breath. But in my heart I’m crying because at my age I should’ve been settled with my husband and my children but instead I feel alone and lost.”

There are all sorts of things you probably didn’t have to consider when you were younger – the baggage from previous long-term relationships, family concerns, children or health issues – but dating later in life can still be rewarding and provide the companionship, affection and support you’re looking for.

Here’s advice on finding love at a later stage in life and tips on how to cope with the challenges this presents.


Experts agree that getting back into the dating scene after many years “off the market” can be daunting.

The first step is just getting out of the house and venturing outside your comfort zone, says Durban psychologist Carol-Ann Dixon. “Go to places where people your age might get together,” she says.

A good place to start would be getting involved in hobbies or group activities that interest you, Johannesburg life coach Siobhan Jonker says. “Do something you love, whether it’s a sport or a hobby,” she says. “If you’re having fun, you’ll radiate the kind of energy that attracts people to you.

“Meeting someone through family and friends is also a great way to connect with others,” Jonker says. The advantage here is it’s a safe space to meet new people.

Before jumping into the jungle that can be online dating (see box on next page), ask friends and family if they know anyone they think you might like and could introduce you to. This might be a better option than online dating where you’re essentially confronted with lots of strangers, which can be unsettling.


Let’s be honest, when you’re no longer a kid, you’re more likely to know what you like, what you don’t like and what you expect from a partner.

“So you may be less open to simply meeting someone and just seeing what happens,” says psychologist Dr Louise Olivier.

This can make dating difficult because you’re too quick to decide someone isn’t for you. Jonker says you need to give yourself time to get to know new people without expecting each new person to be exactly what you’re looking for.

“Approach your date expecting to find out who they are as a person, rather than viewing them solely as a potential mate. That’ll help prevent unrealistic expectations,” she advises.


When you’re older you might feel time is of the essence and not to be wasted, so there might be added pressure for the relationship to advance, Dixon says. 

But try not to rush things. Keep in mind that both of you might be dealing with unresolved emotional issues after the death of a partner or a divorce.

“Being older means knowing people often carry the baggage of their past experiences,” Olivier adds. You need to make allowances for this.

Also, realise that while the idea of being measured in the light of past experiences isn’t always encouraging, it goes both ways. Give the other person the same understanding you’d expect, and realise that this understanding takes time.

“It also means that you need to understand where your own emotional baggage is coming from,” Johannesburg life coach Lindelwa Khoza says.


Being keen to date again doesn’t mean you won’t be anxious about the prospect of meeting new people, says Susan Eksteen, a relationship therapist from Krugersdorp in Gauteng. In fact, it can be quite the opposite when you’re older because you know your body isn’t what it used to be. This brings with it the fear of rejection, Eksteen says, particularly when it comes to intimacy.

When Deborah Moggach, whose novel These Foolish Things was turned into the film The Best Exotic Marigold Hotel, found herself dating again in her sixties, it brought her face-to-face with the realities of ageing

“In a long marriage you and your partner age together . . . you hardly notice the wrinkles and the thickening waist,” she writes in an article published in The Telegraph. “It’s different for people in my position.

When I meet a man he mirrors back to me my own mortality. It gives me a shock to realise I’m that old.


It’s not uncommon for grown-up children to struggle with a parent dating later in life, fraught as the idea is with complex feelings about loyalty towards their other parent and concern for your wellbeing. But they do need to understand that the human need for intimacy and companionship doesn’t change, no matter your age. Don’t exclude your children from your private life or avoid the topic, Durban psychologist Carol-Ann Dixon says. “Talk to them and explain that you’re lonely and would like to meet someone. Adult children can complicate matters by wanting to give their stamp of approval for your new partner.” Tell them you understand their perspective and fears, but don’t be embarrassed by your desire to have a fulfilling relationship. Also bear in mind the reactions of your potential partner’s family. Counselling for blended families is sometimes needed.

And he’s probably thinking just the same.” She goes on to talk about all the physical stuff – “holding your stomach in, embarrassment about wrinkles, bingo wings and so on” – that can make you feel self-conscious and insecure.

But the amazing thing is that “love does work its old magic”, she says. She found someone new.

“He doesn’t mind wrinkles, but then he’s got some himself. We’re both veterans of the romantic merry-go-round and have the scars to prove it.” It’s important to be comfortable with yourself, says Khoza.

“The more you like yourself, the better the chance that others will like – and even love – you too.

Do’s and Don’ts


Be honest – with yourself and the other person – about your expectations.

Be flexible without straying from your principles.

Make your time together fun and exciting and not simply a session in which the other person is being interrogated about his or her life.

Tell your prospective new partner if you’re an involved parent but talk about things other than your kids as well.

Give yourself and the other person time to get to know each other without expecting a serious love affair at the drop of a hat


Compare your date with your previous partner.

Fear rejection.

Get discouraged too early in the process.

Get clingy too quickly – it will scare prospective partners off.

Discuss your financial affairs with the other person early in the relationship – trust must be earned.

Think you can change someone’s habits – be willing to take them as they are.

Become intimate too quickly because then it’s difficult to backtrack and allow the relationship to grow gradually.

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