What I Learned About Love From Dating a Wyoming Cowboy

Jason Hoffman/Thrillist
Jason Hoffman/Thrillist

Your early 20s: the perfect age for dating clichéd men and women in order to learn valuable life lessons. There's the tatted-up rebel, the doofy jock, the pretentious hipster, the real-life cowboy... oh, was that last one just me? I’ll start from the beginning.

At the time, I was an uninspired beauty editor in NYC looking to discover beauty in something bigger. I craved more excitement, creative fodder, passion. In my time of ambivalence, I fell for the pursuits of my best friend of eight years, Jack, who had moved out to Wyoming to live life as a wrangler. A long-distance relationship with a guy working on a dude ranch two timezones away? My naïveté never shied from the impractical. We decided to give it a go.

When I visited Jack out in Wyoming, I was awestruck by the idyllic scenery and notion of it all, and dutifully walked around with a notebook and pen the whole time. Times Square has nothing on the ripple and sprawl of the badlands. Perhaps I’ll move here, mused my 23-year-old self. I could become the next Annie Proulx. I could ride my horse to breakfast each morning. Jack would be my cowboyfriend and we would have a perfect life together.

Or -- as it thankfully turned out -- the relationship could just provide invaluable lessons learned for the future. Jack taught me a lot... about when to move on.

If you always come second to the job, you're screwed

Jack’s workday started at 6am. He led trail rides, lunged horses, made repairs around the ranch... you get the idea. I didn’t question his exhaustion by day’s end because ranching was clearly a taxing job. But when your boyfriend frequently claims he only has energy for an hour of catch-up over Facebook Messenger -- the Roy Rogers of communication forums -- you pour another glass of pinot grigio, cry, and ask yourself how that’s fair. The thing was, my busy day also began at 6am. It didn’t matter that I spent it interviewing Heidi Klum for an article before heading to an event at the Plaza Hotel. For me, talking to Jack was always the highlight. Never a chore.

The same guidelines apply to all guys I’ve dated since -- especially the button-up who frequently canceled our plans and got high off closing deals for JP Morgan at 10pm on a Saturday. Someone who wants to make time for you, will.

Dating your best friend has its consequences

When Jack and I were just buddies hanging out and he muted a girlfriend’s phone call with an impartial, "Eh, I’ll text her later," I didn’t stand on my "girl code" soapbox to sermonize about how much that shit upsets women. Funny how those tides turned once I became the lover he scorned. I didn't shrug off the way he ignored my calls. When he made "casual dinner plans" with an ex -- something I would’ve once advised him against as a pal -- I considered them treacherous and unforgivable. But fighting and breaking up with Jack seemed scary. The question arose: could we be friends again after that?
No. We couldn't.

"Boy friends" and "boyfriends" are best as separate categories. There’s too much to lose.

Never change for someone

Jack loathed the hustle of NYC and said I’d have to move out West if we were to be together. He also insisted I leave behind my metropolitan wardrobe. "Don’t be that girl wearing heels in a jeans-and-boots ranch town," he said. "That’d be embarrassing."

Look, I’m not that girl -- I loved rocking cowboy boots and sipping whiskey at his local (read: only) tavern. But I also love wearing stilettos and a dress to a wine bar in the West Village. That’s not embarrassing. If a relationship should bring out the best, truest version of you, why should I box up a huge part of my persona to fit someone else’s mold? I shouldn't. None of us should.

Common interests aren't the same as common goals

Jack and I seemed like the perfect match. Aside from our mutual love for all things horses, we both also enjoyed country music, quoting Family Guy incessantly, and gargoyle-ing to the coffee pot each morning.

But over time, I saw all the red flags. Jack had no plans to leave the one-room Wyoming cabin he called home. His views on marriage were unclear. He didn’t ever want children. Yet even if I accepted those magnificent mountains in view as my landscape, the picture of my future still included a Pinterest-style wedding, two kids, and a colonial house with plush white sofas and a china cabinet. Bottom line? Our futures didn't line up at all.

But then I realized my life was not a Taylor Swift song from 2004.

Of course, I hesitated to bring this up with Jack. Talking about the future felt too... aggressive. But after a certain amount of energy and time, discussing long-term goals eventually isn’t too aggressive. It’s crucial. I missed the boat on that and suffered dearly for it.

I’m not saying that I’ve made every first date since Jack play M.A.S.H. with me on a cocktail napkin. But Johnny Cash and Peter Griffin aren’t strong enough glue to make a relationship stick.

Don’t get swept up by the idea of someone

Sitting on his front porch the last night of my visit, Jack crooned Old Crow Medicine Show lyrics while strumming his guitar, a fifth of Buffalo Trace next to his Tony Lama boots and a Stetson on his head. I imagined us galloping off into the saccharine Wyoming sunset together, forever.

But then I realized that my life was not a Taylor Swift song from 2004. The idea of it all was exhilarating and the shock factor was certainly there; but once that wore off, I’d still be in a relationship with someone who was already living out his dream, solo. I could join, or he could be happy without me.

And with that, I chose to board my return flight home to LaGuardia, happily knowing the next sunrise I’d see would be coming over Manhattan.

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Brooke Sager is a contributing writer for Thrillist. She’s still living in NYC with one pair of cowboy boots and her entire stiletto collection. Her Twitter handle should now make sense to you: @HIHEELZbrooke.