I wish I'd never split from my rich university boyfriend... then I'd be married to someone who enjoys life instead of my reserved, frugal husband

As I pushed my trolley around Aldi looking for the cheapest rice and pasta I could find to feed the family, I thought wistfully, of my first love, Rupert.

He has, I spotted on Instagram, just returned from a sailing trip in Greece where I imagine he stayed with his beautiful wife and children on a chartered yacht with a personal chef and a skipper.

We, on the other hand, spent our last holiday in rainy Wales in a tiny bungalow. We didn’t go out to eat once because my husband said we couldn’t afford it.

As for foreign holidays, it’s been three years since we got on a plane and I have no idea when we’ll be able to afford to go again.

It’s hard not to compare, and quite frankly, regret the romantic choice I’ve made. I broke up with Rupert 25 years ago, but I still torture myself with what might have been...

I think about how much easier life would be if I wasn’t worrying about energy bills or how we are going to pay for our daughter’s school trip.

I daydream about how wonderful it would be to be married to someone who knew how to enjoy life and didn’t spend half his time fretting about his pension.

I met Rupert on my first day at university in the late 1990s. He was that tall, dark and handsome cliché, beautifully dressed in a Ralph Lauren shirt and preppy chinos. I plucked up the courage to chat to him and, later that night, we ended up kissing.

The next morning he knocked on my door and we went for breakfast. I was completely smitten.

I didn’t realise at first how rich he was. He casually mentioned a flat in Chelsea and then, one weekend, took me back to his parent’s house, a huge Tudor pile with wooden panelling in the hall, in an affluent enclave of Surrey.

Their neighbours included an A-list celebrity and a Premier League footballer. It was a world away from my life, growing up in the suburbs of a small town in the Midlands.

When we were still students, Rupert took me to a restaurant in London’s Knightsbridge, which, he told me, was one of Princess Diana’s favourites. He flew me out to his parents’ holiday house in Palm Springs — to this day, the only time I’ve ever flown first class. The whole thing was hugely exciting. Not having to worry about money gave him a charm and a lightness which I’ve never encountered again in my life.

Yes, we were only 18 and we obviously didn’t have much to worry about, but I loved the fact that he didn’t take life too seriously.

That’s pretty much the opposite of my quiet, reserved frugal, husband, a grammar school boy from the North. He is a saver rather than a spender and everything, even a day trip with the children, has to be planned weeks in advance.

Our daily life is hardly what I would call a struggle, but even though Daniel earns a good salary, we are constantly worrying about money.

My part-time job doesn’t go far so we are mostly reliant on his income.

Every time I suggest doing anything spontaneous, like visiting a theme park or even going to the pub with the kids, he makes some sort of an excuse not to go. I find myself wondering how did this end up being my life?

I have to admit to looking up Rupert’s wife online, too.

I Googled her and found a work video of hers, which I’ve watched several times. She actually looks a bit like me and she doesn’t seem, from what I’ve read, to be that posh either.

I wish I had realised how lucky I had been and hadn’t let my insecurities get the better of me. Rupert never mentioned money, but I remember being embarrassed bringing him back to our boring, red brick house. Lots of people would probably have been proud of it but I felt it was tiny and cramped compared to his mansion.

I ended up self-sabotaging the relationship by kissing the captain of the rugby team, whom I didn’t even fancy, one very drunken night. Rupert dumped me the next day.

I sometimes fantasise about what it would be like if we ever met up again.

Years ago, I did see him, at a mutual friend’s 30th and we had a lovely chat. I got a bit drunk and flirty and I remember him gently putting his arm around me to steady me after I stood up suddenly to say hello to someone.

He looked just how I remembered him and we chatted like old friends.

I know that by now, more than two decades later, I really should have moved on, but I haven’t. It’s one of those Sliding Door things.

Logically, I realise that if we’d gone on to marry, there would probably have been things about Rupert that would have driven me mad. He probably snores, spends ages on the loo and forgets to pick up the milk on the way home, like my husband.

But I bet he isn’t permanently filled with angst about money — and I bet his wife doesn’t have to put back any luxuries, even in Aldi.

You live and learn, as they say, but if I could go back in time, I would tell my 18-year-old self that she should never let him go.

*Names have been changed