How to Date Your Friend's Sister

You’re an older kid—you have that college boy, sweat, and cheap cologne smell. When you went over to your friend's house for a post-soccer-game hangout turned sleepover, she walked to the bathroom across the hall in a gray oversized t-shirt, stopped in the door frame, and smiled that brace-filled grin.

That metal smile is now white and beckoning to be kissed. The oversized shirt is replaced by a pink crop top and high-waisted shorts. She is hot, but she doesn’t know it yet. She's into you, but then there’s your friend. Your pal. You call yourselves brothers. To date his sister would be wrong. You’ve talked about it. “Your sister is hot, man,” you’ve said after a couple of drinks. Your friend leans down, sober as a priest, and says, “If you touch my sister, you die.”

So what do you do?

Take a seat, fellow hunter. Come into my fold—under my wing. I am going to let you in on the mythical journey of figuring out how to date your friend's sister.

Weigh the Costs

Take a step back in your joggers and sneakers. Sip some whiskey, look out your high rise apartment window and think: Is it worth it? At very best, you and your friend’s sister get married, make a family, live wonderfully, and your pal can visit you and his family at the same time, knocking two birds with one stone—and loving you all the more. At very worst, your friend and his family will forever curse your name. You have to buy a gun because the cars driving by late at night keep you wide-eyed under the covers. Your therapist says to let it go, but you won’t until your friend does. You both hold grudges until the stress and ulcers kill you 20 years early, and you are mythologized as the guy who put hoes before bros.

Is it worth losing your friendship over this girl?

If you date and fall short of anything besides eternal marriage, your friendship will likely be jeopardized. To be honest, the chances are stacked against you. Men from the beginning of time have tried and failed to date friends’ sisters, and most of the scenarios have ended catastrophically. The Trojan War—the fall of the Roman Empire.

OK. Maybe not, but you could lose a friend. And that’s a big deal, especially if you’re like me and only have two friends.

Ask for Permission

Now that you’ve decided to test your fate, this is the most difficult yet most important step. If you’ve ever seen a Bud Light commercial, then you know about the bro code. For those who don’t know, the bro code is a list of trivial rules that haven’t meant anything until now. If you get with the sister, it’s only a matter of time before he finds out. At that point, even if he doesn’t care, he will be mad that you didn’t tell him. This step is the best chance you have at maintaining a friendship.

Listen close, because this step has several points. The first step in gettin’ the sis’ is selling your friend on what he wants: A solid future for his sister and a bro for life. You can grant him these wishes. You are the gene leaving the prison of the dating pool for a better life in the family of your best mate. You can change your stars—if you clean up your fucking act.

That’s right. No more hookers, happy endings, strip clubs, or bar crawling to motorboat thirsty bitches. Even if your friend wants to, you must refuse. If it helps, retire to the mountains, practice meditation and yoga, or learn to hold your left arm upright while you sleep as a form of strength and penance. Live the ascetic life, refusing to indulge until you master the natural world. For a solid year, you must live a monk’s life to prove to your friend that you are worthy. You must show him that you are not a player. Nobody wants their sister to date a sleazebag.

Then, convince him of the benefits to be reaped from permitting the transition from best-friend, to best-man, to brother-in-law. Family reunions will be fraternal in every sense. You can slip out during grandpa’s long racist speeches to sneak a bong-rip and shot in the truck of your car, just like the good ol’ days. His mother will commend him for spending so much time with the family, and his sister will love him for all the spontaneous pop-ins. If you end up wifing his sister, it can only work out in his favor. Let him see that. Teach him. Help him help you.

Move Slow

Now that you have your buddy’s blessing, you will be tempted to jump into things. You already know the girl from her brace-faced, ugly years. Resist the temptation! Take things slower than usual. Treat her like a goddamn lady. Be nice to her parents. You have chosen to gamble, and now you have to prove yourself to both her and your friend. The success of this relationship will likely determine the future of your friendship. This is no girl at the bar that is one drink and compliment away from going home with you. This is your life—and her life. Treat her well, and move slow.

Take her on nice, planned dates. Hold her hand and walk downtown. Kiss her at each street crossing. Tell her she’s beautiful. Leave her notes. Hug her from behind. Tell her you love her laugh. Remember that what you have is real, and there is nothing more satisfying and titillating than being in love. You can still be a bro. You can still drink PBRs and talk like a twelve-year-old who’s just learning to swear. You can still get the meat-sweats after pounding 20 $1 burgers. But when it comes to girls, you’re the captain now. You have his sister, and that shit is sacred.