The one that got away: missing out on buying the house you love

I still think about the one that got away. It was a charming two-storey terrace house in Newtown with a desk nook tucked under a stairwell and a tiny patch of green that passed for a backyard.

Maybe it was the address – Angel Street – that made it seem so perfect. Or the fact property prices in that part of Sydney have trebled since I went to the open home more than a decade ago. For whatever reason, that house has stayed with me as the one I let slip through my fingers.

In reality, that home was never within my reach. I was living in another city, finishing a degree while starting a cadetship. The house hunt was for a (now ex) boyfriend who had just returned to Sydney after a stint overseas.

Since then, I’ve accumulated a husband, a couple of children and a mortgage of my own. So why has that house stayed with me? Is it a symbol of a path I never took, a life I never lived? Regret is too simple a word for it but a certain nostalgia flickers across my consciousness now and then when I think about that place in Angel Street.

Perhaps the feeling of missing out is inherited. My Sydney-born-and-bred father remarks so regularly on the grimy past of now-fashionable inner-city suburbs that we have a running joke about how he could have bought all of Surry Hills (and half of Redfern) if only he’d invested more wisely.  

His father, who fled crushing poverty in rural Ireland in search of a better life in Australia, had his own tale of loss. (Not that we ever discussed real estate before he died when I was 11 – he was too busy teaching me how to roll cigarettes and letting me sip the froth off his Guinness.)

My grandfather worked a series of blue-collar jobs, from driving a taxi to assembling auto parts. After his marriage collapsed, he invested money from the sale of the family home in the stock market, buying shares in an obscure nickel mining company.

The stock boomed. When my grandfather learned smoking and drinking were about to be banned in the boarding house where he was living, he offered to cash in his shares and buy the entire building. But a temperance group had already purchased the property (hence the new rules), so he held onto the shares. Poseidon went down as a one of the great collapses in Australian corporate history. My grandfather’s paper profits turned to dust.

Writing on romance last year, the English author Jeanette Winterson described nostalgia for lost love as “cowardice disguised as poetry”.

“It is easy to imagine that if life had moved a degree in a different direction, then the one that got away would be by our side, and we would both be living happily ever after,” she wrote.

But sighing over fantasy, she warned, “drains energy from reality.”

Bob Montgomery, an honorary fellow at the Australian Psychological Society, says it’s normal to have regrets about mistakes such as not taking an opportunity when it presented itself.

“It’s just such an ordinary part of life,” Montgomery says. “But the more you focus on and stew over your mistakes and your failures, the more quickly you will make yourself depressed.”

The best course is to come to terms with the past, learn from it and move on. And what of the next potential dream home?

“Weigh up the pros and cons, because impulsive decisions you will often regret,” Montgomery says. “Do some reasonable background research and when you get to the point where you think on balance this looks right, you owe it to yourself to take the step.”

Of course, the anticipation of an event is often more enjoyable than the reality. I never did check whether Angel Street was under the flight path.