Home US I wish I had never split up with my rich college boyfriend… then I’d be married to someone who enjoys life instead of my reserved and frugal husband.

I wish I had never split up with my rich college boyfriend… then I’d be married to someone who enjoys life instead of my reserved and frugal husband.

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My husband and I spent our last holiday in rainy Wales. My ex, on the other hand, just returned from a sailing trip in Greece.

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

From what I saw on Instagram, he 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 captain.

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

As for holidays abroad, we haven’t been on a plane for three years and I don’t know when we’ll be able to afford to travel again.

My husband and I spent our last holiday in rainy Wales. My ex, on the other hand, just returned from a sailing trip in Greece.

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

I think about how much easier life would be if I didn’t have to worry about energy bills or how we were 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 their time worrying about their pension.

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

The next morning, he knocked on my door and we went to breakfast. I fell completely in love.

At first I didn’t realize how rich he was. She casually mentioned a flat in Chelsea and then, one weekend, she took me to her parents’ house, a huge Tudor-style mansion with wood paneling in the hall, in a wealthy enclave of Surrey.

His neighbors included an A-list celebrity and a Premier League footballer. It was a very different world to my life as I grew up in the suburbs of a small town in the Midlands.

When we were students, Rupert took me to a restaurant in London’s Knightsbridge that he told me was a favourite of Princess Diana’s. He flew me to his parents’ holiday home in Palm Springs (to this day, the only time I have ever flown first class). It was all very exciting. Not having to worry about money gave it a charm and lightness that I have never found again in my life.

Yes, we were only 18 and 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 Northern elementary school kid. He’s more of a saver than a spender, and everything, even a day trip with the kids, has to be planned weeks in advance.

Our daily life is not what I would call a struggle, but even though Daniel earns a good salary, we are constantly worried about money.

My part-time job doesn’t go very far, so we mainly depend on his income.

Every time I suggest doing something spontaneous, like visiting a theme park or even going to the bar with the kids, he makes some excuse not to go. I wonder how my life ended up like this.

I must admit that I also looked up Rupert’s wife on the Internet.

I googled her and found a video of her work, which I’ve seen a few times. She actually looks a bit like me, and from what I’ve read, she doesn’t look all that fancy either.

I wish I had realized how lucky I had been and not let my insecurities get the best of me. Rupert never mentioned money, but I remember he embarrassed me to bring it back to our boring red brick house. Many people would probably have been proud of it, but I felt it was small and cramped compared to her mansion.

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

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

Years ago I saw him at a mutual friend’s 30th birthday and we had a very nice chat. I got a little drunk and started flirting with him, and I remember him gently putting his arm around me to steady me after he suddenly stood up to greet someone.

It looked just 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 haven’t. It’s one of those things that happens when you’re breaking through.

Logically, I realize that if we had gotten married, there probably would have been things about Rupert that would have driven me crazy. He probably snores, he spends a lot of time in the bathroom and forgets to pick up the milk on the way home, like my husband.

But I bet he’s not permanently plagued by money anxiety, and I bet his wife doesn’t have to give up any luxuries, not even at Aldi.

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

*Names have been changed

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