“Em and I broke up.”

Cyrus tells me this as we sit in the terminal of Boston Logan. It’s a throwaway response, the lowest common denominator to Dustin’s prodding “Did you tell him yet?” The words linger in the air for a moment before I respond with a worthless “sorry”, the sole word I can think of in my dumbstruck state. “How?”

They dated for four-and-a-half years, the entirety of Cyrus’s college career aside from the few weeks that remain after this fleeting spring break trip. They were supposed to be perfect for one another. But then I remember the photos they took: always looking candid, it took a true friend to know they were staged, the two of them freezing their expression the moment before the shutter popped, aiming to suspend their happiness in time. It made me think about all those times he said he didn’t want to have kids; maybe it was less about him and more about her.

“Yeah, so that means you have to help me talk to girls,” Cyrus says. I stare at Cyrus, my eyes blinking as if seeing for the first time.

That could be difficult: Cyrus has a mustache. In fact, we all have mustaches. Dustin had the wonderful idea of us getting “travel-staches” for this trip, and we all bought into it. Cyrus usually wears a beard. Combined with his short hair, he often looks like a well-groomed version of me. Not to worry though: Andy’s looks the worst. It’s much too wide, and when I relay this to Dustin, all he says is, “I knew that would be the best part of the trip.”

Despite his facial hair, Cyrus has the wind at his back; today’s college graduates leave many more women in the sea than men. Unfortunately, since he hasn’t been on the market since high school, he needs helps navigating the world of women who are not in secondary education. I sometimes fear us men are digging ourselves into a hole.  The picturesqueness of Instagram and promiscuity of Tinder leave reality distorted. We believe the only women worth talking to are goddesses and that any sign of engagement signals sexual attraction. Who are we men to think so highly of ourselves?

I sit beside Cyrus as we drive across New Hampshire. The White Mountains undulate beyond the windows of his ancient Civic. He’s never more himself than in the northern reaches of the state. Our conversation endlessly winds between topics, up hilltops and down valleys. Like the sun bounds the Earth, the subjects of women and dating always keep us within their orbit. Cyrus blazes through a monologue on female communication methods, hypothesizing about the body language, the text messages, the pillow talk. Exasperated, he throws his hands off the wheel, sending them thumping against the roof in defeat. I want to help, but I’m often just as clueless as he is.

 

From our plane in Boston, we reach America's other north. In Seattle, we leave behind the woes of New England for the awe of Puget Sound. Everything here looks like home beneath a magnifying glass: the buildings taller, the mountains steeper. By day, we glide up and down the slopes of the city. We push through the congested aisles of Pike Place Market, chewing blackened halibut sandwiches and thumbing through pages at the apothecary. We inhale long, slow breaths of marijuana on our “substance-free” kayak rental, standing on the arboretum that acts as the dividing line between the University of Washington and Seattle University. But by night, the universe collapses to a single reality: talking to girls.

Cyrus and Dustin’s interest in this topic verges on obsession. Andy and I deem them fit to psyche themselves out with their banter (Cyrus, you’re gonna need to find somewhere else to sleep tonight.) but they view it as practice. We meet up with two of Dustin’s friends, here on an unrelated trip, and play shuffleboard in a wooded bar basement. Cyrus wears a checkered-print button-down, attempting to sip his beer with the same suaveness that the Marlboro Man lights his cigarettes.

Dustin’s friends suggest another bar and we all stride into the windy night. They tell us it’s one of the best-known spots in Seattle. Cyrus trails at the back of the group, wide-eyed at the expectation of women. “The Cuff”, I read as we saunter towards the entrance. An older gentleman, leaning against the building while smoking a cigarette, motion us to go in as we approach. “Go in, have some fun!” he says. We heed his advice, and upon entering we find ourselves in a black-lit room surrounded by middle-aged men. We promptly exit and some clubfooted gay man hobbles after us, trying to convince Dustin to have some fun. It turns out “The Cuff” is a gay bar and sex shop, a place as renowned for its lack of women as it is for its cock ring selection.

 

Cyrus has this weird dance move. He squats like he has polio, his knees bending into one another. With his fingers pointed like two pistols, his torso swivels back and forth. It’s funny to watch, but you have to admire his enthusiasm. I feel like that’s often our favorite part of our friends, the goofy side that not everyone gets to see. However, using this approach with strangers – especially women – is hit-or-miss.

 

We find another club. It’s early, so we wander upstairs to some plush chairs and a couch overlooking the dance floor. We figure it’s a ripe time to get high again, and we each eat a pre packaged brownie as we wait for the millennials to arrive. Cyrus stares at some woman down there, trying to get all of us to agree with him that she is the best-looking girl in the place. He and Dustin start to get antsy being upstairs, and they decide to take action. We bestow upon them the “rah-rahs” of courage and wish them the best of luck.

Cyrus and Dustin make their way down to the dance floor. Cyrus sees her amongst the crowd, blonde and in a white dress. Not wanting to come off as desperate, they don’t walk immediately up to them but shuffle their way across the dance floor. Cyrus starts to get nervous, but refuses to be deterred; he has to do this. As they get closer, he realizes he doesn’t know what to say. So long he’s avoided flirtation it’s as if all that data has been erased from his mind. “Hey!” or “What’s up?” is much too casual, likely to receive at best acknowledgment and at worst rejection. Cyrus looks around; Dustin has disappeared, receded back into the safety of the crowd due to his own nerves. Cyrus and the girl make eye contact. He can feel himself start to sweat. Be funny, he thinks, knowing humor is the quickest way to a woman’s heart. He remembers the ordeal he’s just been through and runs with it.

“Is this a gay bar?!” he yells over the music.

The girl looks at her friends, a puzzled look on her face. They all laugh, and then they walk away.

 

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