The dos and don’ts of dating in midlife

Sophie Ziegler’s first go at online dating gave her the idea that would eventually lead to her setting up her own such service - Clara Molden

My husband and I split in 2002. I’d just hit 40 with four young children, and I was the only unattached mum at the school gate with zero friends in the same boat. The sense of freedom soon wore off. I tried dating, running headlong into a “rebound” relationship.

But young children and dating are a tricky mix. Things came to a head when my daughter stowed herself in the back of the car as my “date” and I went out to dinner. We arrived, her head popped up, and she shouted, “You are NOT going to dinner without me!” She was right. Children first, relationships second. Mr Rebound had to go. Nevertheless, I enjoyed being single. With four children (now aged 32, 30, 26 and 24) and a thriving photographic career, I had nothing to prove. I didn’t need anyone.

Online dating was then embryonic. Match.com had begun in the mid-1990s; eHarmony in 2000. The first thing I noticed was how badly men take photographs. Even looking beyond this technical deficiency, I couldn’t envisage a relationship with anyone I saw. Our lives seemed too different.

Then the mid-2000s saw a rash of new dating sites. Plenty of Fish and OkCupid seemed anathema to me. Guardian Soulmates looked more urban, more me, so I ventured forth into the “online” world.

Sophie, pictured with her daughter, found that young children and dating were a tricky mix

Blind alleys and being ghosted

As it happened, my first go at online dating seeded the idea that would eventually lead to my setting up my own dating service. Sifting through Guardian Soulmates with a friend, I came across someone who looked fanciable. “Don’t touch him with a barge pole,” said my friend. “Lethal!” She knew him from way back when. Scrolling down, my friend lit upon a familiar face. I was ahead of her. “Definitely not to be recommended!”

Which just goes to show it is impossible to tell from a 2D image and brief profile what someone is really like and whether they are who they say they are. We pondered a new site, one that wraps the old with the new, where everyone was vouched for. The idea bubbled away in my head.

I managed a few long-term relationships, but I found online dating mentally challenging. Sifting through endless profiles, going down blind alleys and being ghosted, you can take only a certain amount before you feel considerably worse off than before. I managed to avoid disaster-dates but paid for them with tedium. Finally, I struck gold. Three months in, I asked him about Christmas. “I’ve got to fess up,” he replied. “I have a girlfriend. We met just before I met you.

“Women are like buses,” he blundered on. “They all come at once.” I suggested he find another route to use his Freedom Pass on.

Real-life situations

When Covid hit, I decided to take fate into my own hands, and act on that gem of an idea I’d once had. The Otto Connection was born, named after my grandson. Instead of one-on-one encounters, Otto was about meeting real people in real-life situations. How else can you feel the chemistry?

A happy Sophie found her present partner through the Otto Connection - Clara Molden

Eighteen guests showed up to Otto’s debut in 2022, either friends or friends of friends. It grew, all by word of mouth. Now, potential members fill in an enquiry form and then have a Zoom call. One thing that fascinates me about the Zoom call is that I never have any idea what someone will be like at the end of the call based on what they are like at the beginning. That’s one of the lessons I’ve learnt: never to judge on first impressions. I’m interested in people who have something to offer, who are curious, intelligent, fun and unattached. The only no-no is if a candidate is attached.

The monthly subscription is £40. We have academics, bankers, creatives and more, from their 40s upwards. Within this eclectic bunch, some members are happy to stay single; others are looking for The One. We’re now in the hundreds with a 50:50 male-female split, connecting the four corners of England. Next, we’ll go abroad!

There is no “matching” element as such. It is more about putting people together in the same room and seeing what happens. We take part in various informal events which members themselves organise throughout the country, from film trips to lectures, art exhibitions to Perudo matches, quizzes to picnics. We put on foreign trips and throw big parties. The outcome is less important than the event: it’s predominantly about bringing together groups of interesting and interested people who happen to be single.

The Otto Connection puts on various informal events, with the aim of connecting groups of interesting people

I found my “other half” through Otto. Obviously he is our biggest fan, since without it we wouldn’t be together! Rather than banning myself from the events, I’ve made a rule that if a couple meet through Otto they are allowed to remain members, for a while!

But the biggest surprise is it has turned out exactly how I wanted, giving single people a place of their own, a place couples want to join, but can’t! People ask about “success rates”. They mean “people getting together”, and yes, that’s an obvious by-product, but the real success is the sheer joy and happiness of members. I get messages saying, “This has changed my life.” That makes me feel good. But what I’ve learnt in the process has also made me a dating expert – and these are my tips!

Dating in middle age: knowing the terrain

Fancy is tempered by reason and experience; the biological clock falls silent. You have time, space and wisdom to make sensible decisions – only to find a whole new set of headaches to deal with. While youthful dating was an organic, choice-filled experience, you’re now surrounded by smug marrieds who (if they invite you at all) place you at five, seven or nine round the dinner table.

If you’re thinking of exploring dating apps, do so in a spirit of adventure, not “need”. Disastrous dates are a given. Question is: do you curl up in a ball, or cry with laughter? Aim for the second.

Be honest about what you’re looking for. If you want uncomplicated fun, say so in your profile. Be yourself on your dates. Pretence is exhausting, and you’ll never feel truly “seen” or loved.

Life blossoms when we leave fear behind, so be brave. Don’t let fear of rejection rule you. Bertrand Russell was right: “Of all forms of caution, caution in love is perhaps the most fatal to true happiness.” Biases lead to mistakes, but an open mind equals opportunity. Never give up hope; don’t be prescriptive. Love rarely comes as you expect.

Having said that, there are a few rules: avoid mimicking your previous relationship, for one. It failed for a reason. Dump your baggage from that relationship. No one cares about your ex. If you carry the weight of the past, you will fail. Shed all anger and bitterness. Undergo therapy if necessary, but leave that part of your life behind.

There are some sex-specific rules, too. Women… Avoid “mothering”. Men don’t want it. Men… If you insist on seeking a much younger woman, fine, but be prepared to push prams and change nappies.

For both, heed kindness. An overlooked quality in one’s youth, kindness is an essential attribute in later life. Find someone you can laugh with. Looks fade, money comes and goes, but laughter will see you through.

In the era of #MeToo, men are expected to be strong but vulnerable, driven but sensitive; they are expected to take the lead but not be controlling. Give them credit for trying.

Finally, don’t ghost people. It’s cowardly and rude. A bit of positive feedback never goes amiss.

Dating in your 40s

People dating in their 40s should avoid rebound relationships and not settle out of fear of being alone - FluxFactory/E+

• Most divorces happen during this decade, but singledom doesn’t necessarily bring independence. Romantic prospects are liable to be intercepted by child care and career. Coming second to your partner’s children is normal, not rejection.
• Don’t rush to introduce, still less amalgamate, your respective children. Your partner is dating you, not your children. You’re looking for a partner, not a father/mother to your children.
• Let things unfold slowly. Never plan your entire future on your first date.
• Avoid rebound relationships. Take your time to find what you want rather than rushing into something you might regret. Don’t settle out of fear of being alone.

Dating in your 50s

Those dating in their 50s shouldn’t panic about empty-nest syndrome but see it as a positive step - 10'000 Hours/Digital Vision

• The empty nest looms. Instead of panicking that your busy life is about to become a barren wasteland, try to see this as a positive step. You’ll have freedom and time to tick off life’s to-do list.
• Your adolescent children may be opinionated. While they may assume expertise on the matter, your children probably have no more idea of what makes you happy in a relationship than you do about theirs.
• The present focus on the menopause overlooks the andropause. Communicate and be compassionate.
• Avoid comparison to younger men or women. You are wiser, more knowledgeable and should feel confident: these qualities have force and beauty.
• Be open to different ways of sharing. Communicate how you see your life panning out. Don’t close your mind to how others see theirs.

Dating in your 60s

The marriage rate of people in their 60s has risen by at least 46 per cent since the mid-2000s - Riska/E+

• Everyone’s wobbly bits go south. So what? Chemistry is ageless. Sex appeal is more about confidence and attitude than looks and latitude.
• Be prepared to deal with loss: empty nests, dying parents and retirement. Let it spur you to realise your dreams and more. Venture outside your comfort zone.
• Never give up on love. Don’t believe me? Ask the Office for National Statistics: the marriage rate of people in their 60s has risen by at least 46 per cent since the mid-2000s.
• According to a study in Psychological Bulletin, this is the decade when you are statistically at your most confident and assured. Your experience is a superpower, not baggage.
• Don’t bang on about health issues. Nothing is more boring.
• Keep feeling confident in yourself. You have more knowledge and accumulated wisdom than ever before – so long as you can remember it.

As told to Rory Ross

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