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 cart through Aldi looking for the cheapest rice and pasta I could find to feed the family, I thought wistfully of my first love, Rupert.

I saw him on Instagram and he just got back from a sailing trip in Greece. I imagine he was there with his beautiful wife and kids on a chartered yacht with a personal chef and skipper.

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

As for foreign holidays, it’s been three years since we were last on a plane and I don’t know when we’ll be able to afford to go again.

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

I think about how much easier life would be if I didn’t have to worry about the utility bill or how to pay for our daughter’s school trip.

I fantasize about how great it would be to be married to someone who enjoys life and doesn’t spend half their time worrying about retirement.

I met Rupert on my first day at university in the late nineties. He was one of those tall, dark, handsome clichés, dressed beautifully in a Ralph Lauren shirt and preppy chinos. I plucked up the courage to talk to him and later that night we kissed.

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

I didn’t realise how rich he was at first. He mentioned a flat in Chelsea in passing, and then took me back one weekend to his parents’ house, a vast Tudor pile with wood-panelled hallways in a wealthy enclave of Surrey.

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

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

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

That is quite the opposite of my quiet, reserved, frugal husband, a high school boy from the north. He is more of a saver than a spender and everything, even a day out with the kids, 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 worry about money all the time.

My part-time job is not far away, so we rely largely on his income.

Every time I suggest doing something spontaneous, like visiting an amusement park or even going to the pub with the kids, he makes some sort of excuse not to go. I wonder: how did this end up being my life?

I have to admit that I also searched online for Rupert’s wife.

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

I wish I had realized how lucky I was and not let my insecurities get the better of me. Rupert never talked about money, but I remember feeling embarrassed when I took him to our drab red brick house. Many people would probably have been proud of it, but I thought it was small and cramped compared to his mansion.

I ended up sabotaging the relationship by kissing the rugby captain one very drunken night, whom I didn’t even want to kiss. Rupert dumped me the next day.

Sometimes I fantasize about what it would be like if we ever met again.

I saw him years ago, at a mutual friend’s 30th, and we had a nice conversation. I got a little drunk and flirty and I remember him gently putting his arm around me to calm me down after I suddenly stood up to say hello to someone.

He looked exactly as I remembered and we chatted like old friends.

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

Logically, I realize that if we had been married, there would probably be things about Rupert that would have driven me crazy. He probably snores, spends ages on the toilet, and forgets to pick up the milk on the way home, just like my husband.

But I bet he doesn’t have constant money worries, and I bet his wife doesn’t have to buy luxury items anymore, not even at Aldi.

You learn everything, as they say, but if I could go back in time, I would tell myself never to let him go as an 18 year old.

*Names have been changed