Pros and Cons of Dating: Someone You Went to High School With

by Allison Davis

Pro: His mom still thinks of you as the sweet girl she knew in high school who her son drove home after math club.

Con: You better hope he thinks you took a seminar to learn how to do that upside down spin move, and that it’s not a result of the triple-digit number of guys you’ve banged since senior year.

Pro: You can fart in front of each other waaay sooner than you would be able to in a normal adult relationship. Like, eight months sooner. Just let it go. Same goes for nose picking.

Con: Talk about bringing up old shit. “You’re so inconsiderate. This is just like right after Tupac got shot the first time and you made out with Liza behind Safeway instead of being with me. YOU KNOW HOW I FELT ABOUT TUPAC!”

Pro: You’re instantly part of the family! You’ve already been through the awkward getting-to-know-each-other’s-relatives process, at a time when awkwardness was expected and you were both going through your blue hair/patchwork pants/thuggish exploratory phases. His parents are just glad you blossomed into the wonderful young woman you are now, and you’re relieved to finally not have to explain your batshit crazy uncle/locked-up sibling/three dads.

Con: You’re instantly part of the family. That means instantly part of dropping a couple hundo on Christmas presents, instantly involved in the dinner table family drama, and instantly expected to pick up Mom dukes from the airport when he can’t.

Pro: Because your friendship harkens back to the days of playing video games and being excited about Hot Pockets, he can dive into that “happy to do nothing” pool that lives just behind the “I don’t even bring my wallet on first dates” stream that most guys get to swim in.

Con: The first time you get a case of Natty Ice and head to Dave’s house to “hang out,” it’s nostalgic. You know, getting together with the old gang, taking off your shoes, being quiet going in and out, bongs. The second time you’re like, “How come Dave never moved out of his Mom’s house?” and the third time you realize that this is what your ‘crew’ does. Every. Single. Weekend.

Pro: Any raggedy bitches hanging out in the background waiting for a crack in your relationship should be discouraged by the fact that you’re so nice, he had to get to know you twice. You got years. History with this man. Private jokes that she won’t understand because she wasn’t AT that particular homecoming dance. You don’t even have to slit your eyes at her to for her to hear, “Step off, raggedy bitch. I got this”.

Con: So, when are YOU TWO gonna get married?

Previously: Pros and Cons of Dating Someone You Work With.

Allison Davis is a writer and TV producer living in San Francisco. If you were to run into her at a cocktail party she would probably casually name-drop HBO, CBS, PBS, FOX, Converse, Chipotle, Piano Fight and Current TV before mumbling something about needing a martini and leaving abruptly.