One gorgeous Autumn evening in Boston, probably in 2009, Cathy and I were at Fenway watching the Red Sox. I got a text from a friend with whom I hadn’t spoken in a while, Chris Powell. Chris and his wife Steph were old friends from high school. We loved them dearly. The text read, “Spend New Year’s in Vegas with us!”

My immediate thought? Hell, yeah! I think I might have even responded with a “Hell yeah.” I showed it to Cathy. She smiled. “No, I don’t think so,” she said. Neither of these reactions came as a surprise. Cathy and I do well at balancing each other out. She has more of a “save it” mentality when it comes to money; I have more of a “spend it.” This is just one of the 200 ways in which we land on opposite sides of important matters. It’s what makes us so adorable.

I have no doubt that these tendencies of ours come straight from our parents. Cathy’s parents didn’t spend a lot as she grew up. There weren’t many family vacations, there weren’t a ton of toys cluttering the house. Rich and JoAnn both came from families that either didn’t have a lot of money or didn’t do anything with the money they had. These things tend to get passed down.

My parents on the other hand, had a…unique relationship with money. We were squarely middle class. They were both educators, which gave them summers off. And I remember that we definitely made the most of them. Growing up in central Arkansas, we traveled to see both sets of grandparents — one in Florida, one in Texas — quite often. I also remember trips to Cancun, Puerto Vallarta and the Dominican Republic. This is not by way of bragging or comparing myself to anyone. It’s more to establish the kind of relationship with money I had growing up.

Anyway, after the game that night, as Cathy and I rode the Green Line back to Brookline, we talked about the idea that Steph and Chris had presented us. “It’s going to cost a lot,” she said. “We’ve already been to Vegas. I don’t need to go back,” she said. I had no legitimate responses to these points, other than to say, “But it’ll be so fun!” We didn’t have kids at that point. We were both gainfully employed. “Come on!” I said. “No,” she said. And she eventually wore me down.

I know I’m making her sound like a stick-in-the-mud, and I know she doesn’t like it when I tell this story. But I think it’s important to remember this one, as it has always stuck with me. The trip, I assume, would have cost around $1,000. Maybe more, maybe less.

I’m not sure what we did with that $1,000. Maybe we saved some, maybe we paid some bills, maybe we bought some nice Christmas presents for our family members and ourselves. I don’t know. But what I do know is that I can’t sit here right now and tell you the story about the one time we dropped everything and spent a crazy New Year’s in Vegas with two of our best friends. Those memories, those stories are worth more to me than any dollar amount I can think of.

There’s a danger in being too careless with money, but I also believe there’s a sadness in being too careful with it. The memories you make and the times you spend having fun with your friends end up shaping your life. Those are the moments you look back on, the ones that fill your heart and give you a real sense of love and comfort.

So get out there, god damn it. Go see your friend in Chicago, the one you haven’t seen in ten years. Live your life. it’s gonna be gone before you know it.

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