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Reading: ‘I’m done with grumpy old men’ – woman celebrates toyboy romance with partner 33 years younger
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Need To Know > Lifestyle > ‘I’m done with grumpy old men’ – woman celebrates toyboy romance with partner 33 years younger
LifestyleSex

‘I’m done with grumpy old men’ – woman celebrates toyboy romance with partner 33 years younger

Andy Crick
Last updated: November 11, 2025 3:57 pm
Andy Crick Published November 11, 2025
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Elaina St James isn’t interested in men her own age – and she’s not apologising for it.

The 56-year-old model from Chicago has sparked a storm online after declaring she only dates men in their 20s, insisting older guys simply can’t keep up.

Her current boyfriend is just 23 – making him 33 years her junior and the youngest partner she’s had so far.

But according to Elaina, he’s also the most exciting.

In a viral Instagram video that’s been viewed nearly 28,000 times, she explained exactly why she’s sworn off dating men her own age.

Speaking to Nude Newz, she described her younger lover as sweet, laid-back, full of energy – and blessed with a great physique and a full head of hair.

For her, younger men bring a sense of playfulness and vitality that their older counterparts have lost along the way.

While she won’t date anyone under the legal drinking age, she says she can’t imagine being with someone over 40 again.

‘They become grumpy old men,’ she said, according to Nude Newz.

Elaina previously dated older men but grew fed up with the monotony, health problems and lacklustre intimacy.

‘It was just the same thing over and over – one position, no spontaneity,’ she said.

‘Sex felt like a chore.’

By contrast, she claims her younger partners are enthusiastic, attentive and genuinely thrilled by her body, which she describes as ‘exotic’ to them.

She’s even embraced being labelled a ‘milf’ or ‘cougar’, saying it’s empowering to still be seen as a sexual being in her 50s.

But it’s not all about the bedroom.

Elaina says younger men come with far fewer complications.

‘Older guys are worried about retirement, alimony or grown-up problems,’ she said.

‘Younger men have fun money, want to go out and enjoy experiences.’

READ MORE: Super fit gran, 65, feels ageless after key diet change

While she’s not looking for marriage or anything long-term, she insists these flings are exactly what she wants right now.

The model recently posted a video listing her top five reasons for dating men in their 20s – including being healthier, more active, less dramatic and more open to older women.

Unsurprisingly, social media was split.

‘I support this decision! I’m 25,’ one commenter wrote, while another replied: ‘Yeah, good luck with that.’

Others chimed in with flirty messages, though some questioned whether the dynamic would really last.

For Elaina, though, the message is clear: she’s done with dull relationships and is embracing her desires unapologetically.

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