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WHEN IT COMES to things I've consistently done on an annual basis, for most of my life it's been limited to 'Go Home to New Jersey for Thanksgiving,’ 'Go Home to New Jersey for Christmas,' and, well, that's about it. That changed around a decade ago.

The first time I went to Las Vegas, it was technically for a work trip. It was early in 2017, and I was shadowing a celebrity for a profile story. When I came back and said it was a pretty good time, my friend—who I’ve known since kindergarten—had a moment of inspiration. We decided that we'd head back to Nevada together. Because why not? We pegged our first Las Vegas trip to the first weekend of the NCAA March Madness tournament.

We knew we wanted to stay on the Strip, because that's the image that comes to mind when you think of Vegas. So we found one of the cheapest places to stay, using the age-old adage: It's just a place to sleep. And that we did. The best way to describe that first hotel room is through another well-worn expression: You get what you pay for. The room was 100% outdated—the kind of hotel room you might find in an ‘80s action movie, where the henchmen are holed up on the road waiting for their next instructions. We’re talking peeling stucco ceilings, sticky comforters, and carpets that look like they’d give you a fungal infection.

Sports betting area with multiple screens displaying live games.
Evan romano
At a Las Vegas sportsbook, you can watch every March Madness at the same time. This one is at The Venetian.

But it didn’t matter, because we weren’t trying to spend much time there. We’d grab beers for the road and drink them as we walked on the Strip (something you can do in Las Vegas—even still) and spent most of our time in the nicer hotels we couldn’t afford.

At the time, betting on sports wasn't legal anywhere else—so the idea that I could put actual money on an actual game was as wild as stepping onto a Star Wars planet. My mind was blown. And that was before I walked into Caesars Palace for the first time and saw about 20 different massive TVs playing every single college basketball game happening all at once. Something must have clicked. I knew this was something I'd be doing over and over and over again.

Indeed, in the years since, this trip has evolved into a full-blown tradition. A few years in, we managed to recruit another of our childhood friends to join. If you ever figure out some kind of a tradition, let me share a tip I've found from personal experience: The more people you get involved, the more real it starts to feel.

The trip has always revolved around three things: Watching basketball, walking up and down the Strip, and eating In-N-Out. Over the years, more activities have filled out the agenda. Good restaurants have entered the mix. It now includes spa treatments, meditation classes, and even cigar lounge hangs. Now that we’re in our 30s, the stucco ceilings and icky bedding have been replaced by high thread-count sheets and hotels where you can get a $30 glass of scotch in the lobby bar.

Want to know the funniest part of all this? After all these years, I feel like I hardly know anything about college basketball anymore. As a Penn State grad, I was particularly hyped for the first year in forever that our school's team was going to reach the tournament. That year, of course, was 2020. The tournament was entirely canceled, as was our trip.

Fast food restaurant sign
Evan Romano
We’ll never outgrow this part of the tradition.

Over the years, our lives have changed in all the ways they can in your late twenties and early thirties. People move, careers evolve, families and responsibilities grow. My friend has moved back to New Jersey. While we still keep in touch all the time, the IRL hangs have become less frequent. And yet, our annual tradition manages to pull us closer together with each passing year.

It's not just the trip itself, but planning out activities, picking out flights, deciding which movies we'll watch while in the air, and how many times we're going to have In-N-Out over the course of the trip. This year, it was a modest two.

Headshot of Evan Romano
Evan Romano
Culture Editor
Evan is the culture editor for Men's Health, with bylines in The New York Times, MTV News, Brooklyn Magazine, and VICE. He loves weird movies, watches too much TV, and listens to music more often than he doesn't.