My 4 Biggest Regrets from This Decade

#1 — Not Getting Married Sooner

If there is a word which gets you blackballed in small talk, shunned at parties, and avoided in the hallways, it is the word “regret.” To speak of regret is a conversational sin. Nobody wants to look bad in front of their friends. Nobody wants to revisit the pain of bad choices.

Luckily for you, I don’t have many friends to look bad in front of, and the pain of past choices accompanies me most days whether I like it or not.

I write about regrets because I’ve learned a ton from watching other people fail. I try to study the regrets of others to be wise. It seems fair to return the favor and tell you about mine.

Maybe you won’t make the same mistakes I did.

And I got married at 23.

Here’s the only way I know how to explain the reasoning behind that:

Kate and I started living together before we got married. She worked as a server at an Italian restaurant. I worked at the school newspaper. I remember the first night we spent in our first apartment. She went to work. I watched cartoons. Six hours later, she arrived home with a Greek pizza. We chewed feta and bread and olives. Halfway through dinner, she said “Oh my god. I forgot to bring ketchup to table seven!”

That’s when it clicked. She had worked hard to pay for the food I was now stuffing in my mouth. During her shift, I’d watched 6 hours of Family Guy. I dim awareness flickered in my brain: she didn’t say a word about this imbalance. She never talked about it. Another thought exploded in my neurons with the force of an atom bomb. She didn’t mind sharing her money with me, a scrawny, goofy kid with pipe dreams about writing. In that moment, I got a taste of what life could be like if she never left.

I knew I should marry her.

I knew it that second.

But I dawdled about buying a ring. I dawdled about asking her parents. I dawdled about proposing. I don’t know what I was afraid of. Maybe it was her father. He still scares me.

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