After my second divorce, I turned to online dating – and it wasn’t what I expected

Dating after divorce: "The whole business of romance had changed since I was last single." Photo / Getty Images

Over the years I’ve noticed that whenever a character turns up in a new television series or film who is American, Jewish, grumpy, neurotic, starved for sex and desperate for love – for example, Larry David, Jerry Seinfeld, Woody Allen – friends always say: “He’s just like you!”

The latest fictional incarnation of me – or so I’ve been told – is Toby Fleishman (played by Jesse Eisenberg), the protagonist of a new American drama Fleishman Is in Trouble, on Disney+.

The series is based on the 2019 best-selling novel of the same name by the award-winning New York Times journalist Taffy Brodesser-Akner. Toby Fleishman is a 41-year-old doctor, living in New York, who after 15 years of marriage is divorced from his materialistic, career-driven wife Alice (Claire Danes), with whom he has two young children.

We first meet Toby – a few months after his divorce – discovering the world of dating apps, which he finds surprisingly erotic.

But his cornucopia of carnal delights is interrupted when Alice dumps the kids with him for an unscheduled stay and then mysteriously disappears. Poor Toby; he has to juggle the demands of work, the demands of being a single dad and the most demanding of all his demands – his newly awakened libido.

Fleishman Is In Trouble seems a throwback to a pre-woke world of Woody Allen’s Manhattan. Let’s face it, the trials and tribulations of affluent, white, divorced men have not exactly been a fashionable topic of late for fiction. But how true to life – at least my life – is this new series?

I was roughly the same age as Fleishman when my first marriage ended in 1996 after ten years. Back then we had no dating apps to turn to for comfort or distraction.

Our 10-year-old son Jack lived with me in the family home and so I did what mums have been doing since time immemorial – cleaning, cooking, laundry, fussing over him – and I loved it.

Jesse Eisenberg and Claire Danes in "Fleishman is in Trouble". Photo / Getty Images

It was dealing with the emotional aftermath of our divorce that was much more difficult for him and me.

There was a new sound in the home: the silence of her absence. He loved staying with his mum and when I went to bring him home after a weekend, I felt I’d dragged him from the fun fair back to the orphanage.

But Toby Fleishman never seems to worry about his parenting skills or his inability to protect his children from the fallout of his divorce. Where is Toby’s guilt? His regrets?

I’ve never met a single dad who did not regularly beat himself up for being a crap or useless father.

It was only in the years following my second marriage that I began to hear about these newfangled things called dating apps. I was suspicious – weren’t dating apps for love’s losers?

And then, having had no luck in finding off-line love, I discovered I was one of those losers. So I signed up to Tinder.

In episode one, Fleishman starts internet dating and straight away discovers a vast army of sexy women who can’t wait to have sex with him. But what the series misses is that sense of trepidation that any divorced person – male or female – feels when they first step into that jungle of digital dating.

Toby Fleishman is like a greedy kid in a sweet shop; I was more like a nervous, sweaty teenager on his first date, but I soon got the hang of it.

When it comes to online dating, Toby Fleishman is like a greedy kid in a sweet shop; I was more like a nervous, sweaty teenager on his first date, but I soon got the hang of it. Photo / Getty Images

I tried different dating apps – OkCupid, eHarmony, Hinge, Our Time – and it wasn’t long before I was going out on dates two or three nights a week.

I met a bondage expert who wanted to put the cuffs on me and a New Age witch who put a curse on me.

The first thing you discover is that all this dating is expensive and exhausting. The second thing I discovered was that the whole business of romance had changed since I was last single.

That said, I must have been the only heterosexual male in the UK to have been on Tinder, but never to have sex. I’m not sure why. I became more interested in the stories of the women whose pictures I saw than in sex or dating them.

It was the little details that intrigued me more than their vital statistics or hot promises: The family photos on the mantelpiece, the crumpled undergarments hanging out to dry, all those sad eyes and brave smiles of lonely women longing for love.

Jesse Eisenberg in 'Fleishman Is in Trouble' in New York City. Photo / Getty Images

The irony of dating apps is that they’ve made romance more possible and, at the same time, they’ve made people less romantic. Men once sent women flowers; now, I have discovered, they sent pics of their privates.

Toby Fleishman gets sent all sorts of sexy pictures from women – bottoms, side boobs, full boobs – whereas I only got pictures of the family dog, cat, goldfish, gerbil and an assortment of holiday snapshots.

And I soon discovered the new rules of the world of digital romance – whatever you do don’t get too gushy or too interested, or you could get labelled a “stalker”.

Fleishman is not looking for true love, he’s after true lust and finds it.

And yes, I confess I had a few one-night stands, which was good for my bruised ego but did nothing for my broken heart.

The thing is that, after a marriage, you become utterly convinced that no one on Earth will ever want to have sex with you ever again.

I’m amazed that anyone in New York would have wanted sex with Toby Fleishman – he’s an angry, bland, self-absorbed ex-husband with a criminal taste in checked shirts.

I did online dating – on and off – for nine years. I found lovers, but I never found love.

Fleishman Is In Trouble has plenty of smart lines and a serious side too.

It tries to deal with the question that every divorced man and woman wants to know the answer to: what happened? How does a happy marriage that starts with love end in anger and tears?

To be honest, I’m still trying to figure that one out.