Oh boy! ‘Why I’m only dating younger men from now on’


Six months ago, I was waiting for a date in London when I had a text from the expected man, apologising in advance for wearing a tracksuit. He’d “cycled straight from school”, he said.

“Oh God,” I thought, leaping up and locking my door, wondering if I was about to be arrested. We’d met on the dating app Feeld and I couldn’t remember how old he was. Legally to be on the site he had to be 18, I told myself, maybe even 21 given the filthier side of Feeld. When you’re dating casually, age feels less important than it does when you’re looking for something ‘serious’ so I hadn’t really checked. He couldn’t be school-age, surely, although I suddenly felt like Humbert Humbert.

It turned out he was 24 and at “acting school”, but he was still the youngest person I’d ever met for a drink in a dating capacity and while it was the start of something new in my love life, it wasn’t a great start — he was wearing sliders.

“We’d met on the dating app Feeld and I couldn’t remember how old he was…” Lucy Holden is only dating younger men from now on

/ Matt Writtle

For a long time I thought older men were the answer to everything (the biggest age difference was 15 years). I thought they’d have their lives completely together and when they didn’t, I felt let down. I expected them to know where they were going in their careers, and expected that this would make them easier to be with as a result.

I quickly saw, though, that they were just as clueless as I was. Most hadn’t managed to get rid of toxic friendships and had sat in the same job for years and years, often wanting change but having too little confidence to make it happen. They had mortgages and needed to prioritise safety over boredom and regret. On the one hand they were more likely to own their own place, but on the other they were way more jealous than younger guys (most seemed to assume I was more likely to be chatted up than them). On top of more obvious flaws, they brought loads of baggage from past relationships to the table. There were more exes, and sometimes even kids.

Plus, most seemed to want me to fall at their feet. They wanted to take control of my life, dictate my friendships and make me bow to their careers advice. Possibly it was the kind of older men I was going for; The three I dated were so egotistical that the relationships just felt very negative. One was a horrible misogynist who cried when I told him I’d slip (10 years ago) with one of my male friends. He’d wanted to know, then claimed it was heartbreaking because he’d gone to a school that taught ‘no sex before marriage’. “What about all the women you’ve slept with outside of marriage?” I thought, shocked. In the long run, it all got a bit demoralising.

I had a text from the expected man, apologising in advance for wearing a tracksuit. He’d ‘cycled straight from school’, he said.

It wasn’t until late last year that I dated anyone younger than me, but now I’m a convert. Partly it was out of necessity. At 32, a lot of my friends have recently been getting married and having kids. At the beginning of the pandemic I left the person who I thought I’d be doing all that with, so now I’m a few steps behind. Though I’m trying not to see it like that. Instead I’m enjoying being single for the first time. But the thing about being in your early thirties and still quite far away from “settled down” is that you have to seek out younger friends, people who are less “M&S Dine In For Two” and more “let’s see where the night takes us “.

Before I even realised it, most of my new, post-break-up friends were younger than me. They started saying things like: “You’re 32? I thought you were my age.” Obviously, I wondered if that was a good thing. During the pandemic I had moved home to live with my parents which left me feeling like I’d failed at all sorts of things: the most serious relationship I’d ever had, freelance life, standing on my own two feet. Did coming across as 25 when I was 32 make me tragically immature?

But then I started dating and thought ‘who cares?’. Culturally, we are in a golden period for age-gap relationships — Kim Kardashian (41) and Pete Davidson (28), Priyanka Chopra (40) and Nick Jonas (29), Sienna Miller (40) and Ollie Green (25), Sam Taylor-Johnson (55) and Aaron Taylor-Johnson (32) — a coterie of empowered women who’ve found themselves invigorated by the powers of younger men.

“Culturally, we are in a golden period for age-gap relationships — take Kim Kardashian (41) and Pete Davidson (28)…”

/ Getty Images

Admittedly, Sliders was a write-off (not grown up enough to know that you should top up someone else’s wine when you top up your own — especially if you’re on a date, especially if the date bought the wine). Afterwards, I went on a date with a 26-year-old pea farmer who knew his way around a pheasant, plucing two for my dinner. In every other way he was utterly lost. He asked me to be his life coach, in bed, which was quite bolstering. Plus, he wanted to know what I thought about everything, rather than just telling me what he thought. Sadly, his immaturity with hangovers killed the passion. I’d been operating fine on them for years and he hadn’t learned the skill yet. The final straw was his mum taking away his car keys when he “basically parked in the house” after a night out. Quite right, I thought, shutting my mouth before he realised I’d probably get on better with his mum.

Sam Taylor-Johnson and Aaron Taylor-Johnson are age-gap pioneers

/ Alamy Stock Photo

After that came The Pianist who reminded me of another perk of young men: they dream big. Life, insecurity and ruinous baggage hasn’t caught up with them yet and so idealism flows. Having been the younger one for a decade and found my dreams “monitored” by older, “wiser” men, I let the young ones I date run all their business ideas past me and then tell them that they can do it all. The Pianist (who, by the way, came to my parents’ house and played an improvised concert on their piano) had started up a company in Bristol to make one of the world’s first flying cars. He’s 28 and it’s a big dream, even for an aerospace engineer — but I believed he’d do it because he was that inspiring.

As he was a young millennial, he didn’t want to sit around and get pissed all the time like the older ones. He wanted to do stuff. Yes, that included taking me to an orchestral showing of Return of the Jedi and to a ceilidh in his students’ union bar but it was fun. After plateauing in bars on dates for so long, this was all refreshing. The only problem with The Pianist was that he wouldn’t hold my hand in public (not cool, apparently).

You have to put up with the constant buzz of Snapchat, they watch TikTok on the loo and you have to explain most cultural references pre-S Club 7

Most recently there was K, who suggested we go skydiving for our first date. He’s 25, also has big dreams, isn’t scared of affection and doesn’t want to sit in pubs all the time. For his birthday — when we were just friends — he wanted to go bowling. I hadn’t been bowling since I was about 13. Now at 32, I got fewer strikes, but could have a pint so a net win I thought. We also went to play darts in a hysterically grotty local social club in matching tracksuits, just for the craic. He asked me to be his girlfriend, cutely playground-style, and I put it off because initially I couldn’t get over the fact he was seven years younger.

I found I was bringing it up all the time in the same way those older men were always mentioning it to me: “Oh my God I’ve just realised that when I was 20, you were five.” To me, that quickly began to feel creepy, like they were revelling in the fact I was “so young”. K asked me early on why I kept talking about it and I tried to work out it out. Perhaps it was just the shock of switching teams from being the younger to being the older. Now it doesn’t matter to me much at all.

I do wonder whether I’m shooting myself hugely in the foot, whether I’ll fall in love with someone much younger who doesn’t want to settle down when I need to. At 32, fertility is something I still think about only vaguely, and ideally I don’t want kids before I’m 35, but with at least a year until I have to start really worrying about it, the younger man thing has kind of blow me away. There’s just something about feeling like Oz Clarke in a supermarket wine aisle just because you know what Vinho Verde is that really works for me.

Priyanka Chopra Jonas and Nick Jonas

/ Getty Images for dcp

Obviously it’s not all highs. You have to put up with the constant buzz of Snapchat (they still use it); they watch TikTok on the loo and you have to explain most cultural references pre-S Club 7. On top of that, you get the older sisters checking out your Instagram, and asking if you’re only dating them for your dating column (what ?). There’s also the Netflix watch history, which bleakly includes the kind of “adult” cartoons people only watch when stoned. You have to choose most of the films, and they always refuse subtitles. Did I mention they get stoned still? The compliments are also a bit unusual. One told me I looked like a painting of what women used to look like. I actively avoided what exactly that meant but I suppose it had something to do with being ‘real’, not hyper ‘done’.

On the flipside, there are way fewer games — and they’ve not used up all their energy trying to impress other dates yet. One of my younger men sent tiramisu to my place of work because he knew I loved it. Their communication styles can be patchy but in exchange you get abs and a full head of hair, and really what more could you want? It’s just all a bit simpler, with the younger ones.



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