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I’m 40 and date men in their 20s – it’s not as liberating as I thought

40 0
03.04.2026

When I tell people that I only date men younger than me, they often look at me with pity, disdain, or ask if I’m having a midlife crisis.

For the record, I’m not. I’m a 40-year-old fabulous geriatric millennial who went from never being allowed a boyfriend to someone’s wife, aged 19, through a forced marriage and then a long-term relationship and a revolving door of “situationships”.

I’ve only ever been single for a grand total of 18 months in my entire adult life. So when I hit my late 30s I finally realised I didn’t really want any “ships” at all. Which is why dating men in their mid-twenties to mid-thirties works perfectly. No strings attached, no future, no emotional admin – just the way I like it.

Part of the appeal is that they’re not looking for anything serious, either. Most younger men I meet are in no rush to settle down. They get to go out with a “hot cougar” (their words, no offence taken), and I get to channel Leonardo DiCaprio. If he can do it, so can I.

What I didn’t expect was what dating younger guys would reveal. Most of them are operating from the same unspoken “Lad Code” playbook.

Of course it’s #notallmen – a lot of them are often funny, kind and emotionally literate – but I have noticed, particularly in the 23-28 age range, they tend to follow the same script. On dates, I hear variations of the following lines:

“Most girls aren’t into that,” when I mention ethical non-monogamy.

“Girls can’t be hot AND fun so you must be hot and crazy” – in response to my dating profile, which is admittedly a work of art .

“You are so confident” – said like a compliment, but often landing with a........

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