9 things to expect from midlife dating

Cosmo Landesman explores the pitfalls of returning to the dating scene

“I’d rather live the rest of my life as an unloved, untouched, lonely and sex starved spinster with red lipstick on my teeth than do that again.”

There’s a scene in the classic rom-com When Harry Met Sally where newly attached Marie (Carrie Fisher) has been talking to her distressed single friend Sally (Meg Ryan) about finding romance. Fisher hangs up the phone, turns to her boyfriend and says: “Tell me I will never have to be out there again.”

Ah yes, the great Great Out There! I know women who in midlife found themselves single and went back to the Great Out There in search of love – and within weeks left licking their wounds. Never again! they declared. As one friend put it: “I’d rather live the rest of my life as an unloved, untouched, lonely and sex-starved spinster with red lipstick on my teeth than do that again.”

What’s dating like in midlife?

If you’re about to head out to The Great Out There you might be wondering: it can’t be that bad, can it?
The short answer is: yes.
The long answer is: yes and no.
And the honest answer is: It all depends on you. Are you determined to find love? Are you bullet proof? What is your capacity for boredom? Can you laugh at a man who makes you want to scream?

Are you determined to find love? Are you bullet proof? What is your capacity for boredom? Can you laugh at a man who makes you want to scream?

These days you hear lots of negative stories about the horrors of the dating scene. Our ancestors used to sit around campfires telling spooky stories of ghosts and monsters. Now women sit around dinner tables (or on video calls) telling each other spooky stories about being ghosted and the monster men they’ve dated and the frauds they fell in love with.

For every tale of romantic disaster a girlfriend may tell you, I can match with a story of romantic triumph.

Don’t be put off by dating disaster stories

For every tale of romantic disaster a girlfriend may tell you, I can match with a story of romantic triumph. Trust me. I know a little bit about the Great Out There. After the end of two marriages and numerous long term relationships, I’ve had to go out there and do a spot of reinvention myself. Plus, I was The Sunday Times dating columnist, a job that involved at times three dates a week. So I know all about the highs and lows to be found in the The Great Out There.

1. Things have changed…somewhat

One of the biggest obstacles to starting over again is fear of change. “It’s a different world from when I was young” is something I often hear from women. They’ve heard all the scary dating stories and are left scared. They worry that the rules of romance have been written all over again and they haven’t a clue as to how to play the game.

If you’ve not been out there for a while let me reassure you that yes, there have been big changes – good and bad – but as the old song puts it: the fundamentals still apply, as time goes by. Technology – in the form of dating apps – has given us more choice than ever and that can be confusing. And the relaxation of moral norms – when it comes to sex and sexuality – has given us more personal freedom and that can be liberating.

2. Yes, dating apps are for midlife

Perhaps the biggest misconception that women over 50 have is that dating apps are for losers or sex-mad-porn-infatuated twenty-somethings. Not so. Used carefully, dating sites like eharmony and SilverSingles can be an invaluable aid to finding a partner. I know three blissfully happy women who found great men online. Ok, they had to kiss a lot frogs first, but they found their prince in the end.

After 50, goes this common tale of womanly woe, you’re finished. You have become an “Invisible Woman.”

This is not true.

3. Dating older men is a new reality

There’s no way I can sweeten the bitter reality of the modern man hunt. Going to the Great Out There is a bit like one of those SAS/Navy Seal survivor courses that test you to the limit. But those guys have it easy to compared to what you will have to endure out there: men with halitosis of the soul; men who are so boring, narcissistic and self-indulgent you will try and pluck your eyes from your sockets to stay awake.

From what female friends have told me, the modern male seems to have lost the art of conversation. Today his favourite topics include: the evil ex-wife, the psycho-ex-girlfriend, the ungrateful teenage children and the bodily aches and pains he’s currently suffering. (Painful knees are a particular favourite of the over sixty.) One poor woman I know was trapped at a dinner with a man who insisted on sharing the history of his hernia with her.

4. …not so different from the ‘good old days’

Has the actual dating experience itself changed for the worse? It’s a mistake to assume that things were better when you were young. That said, we didn’t have to sit across a candlelit table in a restaurant trying to make eye contact with someone who keeps checking their mobile phone.

…they had to kiss a lot frogs first, but they found their prince in the end.

5. May-December romances aren’t rife

One modern myth we need to tackle is the idea that the dating scene is full of men who are only interested in younger women. After 50, goes this common tale of womanly woe, you’re finished. You have become an “Invisible Woman.”

This is not true. Yes, you will encounter plenty of these sorts of men but give thanks that you don’t have to waste your time on this sort of vain and vacuous man. Such men aren’t looking for love, they’re looking for admiration – usually from other men. If you’re sexy, smart and fun to be with at 40 you will be as just as attractive at 50 and beyond.

For many women the prospect of restarting a sex life with a new partner is the stuff of nightmares.

6. Your body is still sexy

Ok. So you’ve found a man with his own teeth and hair and he’s smart and funny – what about S.E.X? For many women the prospect of restarting a sex life with a new partner is the stuff of nightmares. When I asked a friend – who is 58 – what worried her about dating again after so many years she said, “taking my clothes off in front of a stranger.”

Most divorced women have been taking their clothes off in front of a stranger for years – they’re called husbands! When I said this to a friend she quipped, “Yes, but he never noticed when I was naked. Hence our divorce.”

There’s a very simple cure for body image anxiety and it has nothing to do with diets, exercise, surgery or using a blindfold on your partner. I really don’t mean to be patronising when I say this, I just know it is true and want you to believe it: There is nothing sexier than having confidence about the way you look and carry yourself.

One of the most erotic times of my life was while I was seeing a woman in her mid-50s who’d had three children. She had saggy breasts, celluloid galore, a drop bottom, a bulging tummy, bits that wobbled – and that woman was pure sex on two legs! Naked she would strut around the bedroom with such cool confidence it was a total turn-on. Her attitude was: if you want to date a 25-year-old Barbie Doll, then piss-off!

7. His body can be too (despite the nose hair)

“I’ve seen it all,” says a friend. “Stay calm and keep smiling!”

That said, you’d better be prepared for seeing a new and naked male body, ravaged by that vandal called time. “Saggy male boobs, scrotums dangling so low you might step on them, ancient pubes and nose hair from hell! I’ve seen it all,” says a friend. “Stay calm and keep smiling!” is her advice.

8. You need a pubic hair philosophy

What about sex? The biggest change to the sex life of the nation over the past two decades has been due to the impact of pornography. We hear much about the effect pornography is having on the young – particularly young males – but no one mentions porn’s impact on the mature. When my friend Tina, who found herself single after 14 years of marriage, asked one of her girlfriends for advice about getting back out there she was told: “lose your bush and be prepared for anal sex!”

“Oh my God!” I screamed. “Who did this to you?”

I saw this impact up close and personal in 2004 when after six years of marriage I found my self single again and went to bed with a 54 year old woman who had no pubic hair. Not one tiny strand. Zero. “Oh my God!” I screamed. “Who did this to you?”

She patiently explained that women of her generation were starting to wax. And now a lot of older women fresh back on the dating scene wonder what to do: wax or relax? Men of a certain age (oldies like me) grew up at time when pubic hair was the norm. That’s why when Vogue magazine in 2018 declared that the “full bush was back”, men of my age – and I suspect many women – cheered with delight. Ultimately, it’s up to you. If you’re dating a young man then they’re going to freak-out at the sight of a bush. For older men it’s like seeing an old friend.

Is romance a thing of the past?

Given this pornification of sexual practice you may wonder: Is romance a thing of the past? That depends. There are men who will send you flowers and men who will send you pics of their dicks. Men who will send you nice texts and men who never text at all. The trick is to be able to spot the difference early on.

9. You can find love again

Yes, it’s not easy for women over a certain age to find love – but when has finding love ever been easy at any age? Think back to your teenage years and mid-20s. Getting laid was easy, but finding love? No it’s always been hard for most of us.

When has finding love ever been easy?

Yes, finding a good man is hard. But as a man it is also hard to find a good woman. Delissa Needham, a love coach and author of How To Find A Man, believes that it can be done. Women just have to be “prepared to put the work in” and be “flexible”. Delissa tells me, “You can’t expect a man to fit around your needs and life all the time.”

The Great Out There can be a scary place – but only if you let yourself be scared.

The Great Out There can be a scary place – but only if you let yourself be scared. Remember, disappointment and disaster comes with the territory – but there’s no drama that a strong dose of humour can’t deal with. At worst you will have a funny dating horror story to tell your friends – at best a happy ending with a man  you like to cuddle up with. What’s to lose?

– Cosmo Landesman

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