Highway to Hell
Our twenty-first-century rogue tells you how to survive a road trip withan unreformed member of the geek club.
Illustration by Celia Calle

Dear Scoundrel,
I recently bumped into an old high-school friend from Michigan who, like me, moved to New York about ten years ago. I hadn’t seen him since. We were both pretty much dorks in high school, and after I got a hotshot job in finance and learned the joys of swilling Jameson instead of grape pop, I ignored him anytime he’d call to catch up. This time, he mentioned he was heading back to Michigan for Thanksgiving, and when I said I was, too, he offered me a ride. I was so wasted I was like, Hell yeah, road trip! Thing is, other than playing Magic: The Gathering with him during study hall, I barely remember anything about this guy. Now I’m dreading spending ten hours on the road with someone who might as well be a complete stranger. And some sort of computer engineer, at that. I mean, this guy seems like he still plays D&D. I was going to bail, but I lost my last penny in a poker game and Greyhound isn’t even an option. How do I survive this trip without talking about the weather for ten hours?

A road trip is a challenge even if it isn’t the Gumball 5000. I’ve known guys who were best of buds before that trip to Fort Lauderdale, yet when they got back they were sobbing in their respective showers, trying to wash away the weird ness with Irish Spring. Often it’s a case of intimacy overload. The utter lack of hot chicks on the open road means you can’t diffuse uncomfortable discussions (say, about a guy’s mom dying of cancer) by saying, “Dude, check out those jugs.” Sadly, pretty much the only racks you’re going to see will be on station-wagon roofs. And while you can try to turn the trip into one long “In-A-Gadda-Da-Vida” sing-along, eventually you will have to talk to each other. Once you exhaust the two linchpins of roadtrip conversation (sports talk and puking anecdotes), you’ll turn to sex stories, and this is when things can get hairier than a 1970s porn bush. Your bro may just confess that he has a pervy thing for your little sister.

Lucky for you, you don’t have to sweat losing this guy’s friendship—you just need to kill time for ten hours. The majority of those hours should be spent unconscious. I know—fall asleep on an actual friend during a road trip and he’ll use a pencil as an ass thermometer, then stick it up your nose. But in this case you should immediately assert your alpha status by telling the guy you only got an hour of sleep because you were banging these two chicks you took home from Jugs-N-Strokers (an actual biker bar on Long Island). When your sleep aid wears off several hours later, he’ll still be in awe. Act apologetic about drifting off and continue to intimidate him with tales of your über-manliness. Ask him if he’s ever fired a crossbow from a hang glider into the tailpipe of a truck. He’ll realize his life pales in comparison to yours, and instead of bothering you with chitchat, he’ll let you talk about yourself and tell dick jokes, something that passes the time quite nicely, thank you very much.

Just make sure to rein it in at some point, if you want a ride back. During the last half hour you might want to ask him about his family. And his job, of course. Maybe he has some mad tech skills that’ll come in handy.

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