Tits and Ask: Why You Never Bang Your Best Friend’s Sister

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Dear Ken and Ariel: Is it ever okay to bang your best friend’s sister?

KEN SAYS: Bang your best friend’s sister? Why the hell not? And more importantly, why stop there? Does he have more than one sister? Dude, that’s four boobs — and four ass cheeks — you could be motorboarding. Hell, you could even throw in his mom and make it a clean half-dozen. I’m sure your bud would be okay with that. After all, you’re his best friend, right?

Okay, so the sarcasm was pretty thick. But in this case, it needs to be. Because it’s a pretty fucking stupid question. It’s never okay to bang your best friend’s sister. Unless, of course, he’s already banged yours; then it’s open season on everyone, including his dog.

But, assuming he hasn’t, just leave it alone. The hot sister of a best friend is one of life’s Great Dangers, along with “the great aunt who drinks too much and hugs you inappropriately,” “the roommate who thinks it’s okay to sit bare-ass on he couch” and “the chloroform enthusiast who lives down the hall.” If he finds out, you lose a best friend and possibly get your ass kicked. If he doesn’t find out immediately, you’ll still live your life wondering when and if his sister’s ever gonna let it slip. If, God forbid, you fall in deep and start a relationship with the sister, well, then you’re just setting yourself up to lose both a regular lay and a best friend. And there’s still that potential for an ass-kicking.

Bottom line: No matter how alluring or how much of a sure thing she might be, I’d walk away (yes, even me, a guy who once contemplated a gang bang with his mother’s bridge club). And if you need a visual to help shut your penis down, just think of this sister as your best friend in a wig. Got that? Good. There are plenty of women out there who don’t share your brah’s DNA and won’t put you in the awkward position of asking your mail carrier to be your best man.

Of course, if you’ve managed to secure the one best friend in the world who actually encourages you to tear up his hot sister’s ass, then you may need to draft a contingency plan. And forward me his contact info at once.

ARIEL SAYS: This question has generated a veritable glut of sitcom plot points in the latter part of the 20th century, the most famous being Chandler and Monica. Remember all the crazy hijinks those two got up to on Friends before Ross finally realized that–gasp–his best! friend! was! banging! his! sister!? (Although, seeing as he was banging his sister’s best friend for ages, I don’t believe he really had a leg to stand on.)

Of course, Chandler and Monica got married, so America was OK with the banging part. Are you planning on being Chandler to this Monica, or more like Charlie Harper of Two and a Half Men? (Oh wait, Charlie didn’t have a best friend. Now we know why.) This is what you have to ask yourself, because this will not be a wham-bam-see-you-never-ma’am. This will be like one of those annoying family members who keeps showing up at weddings, bat mitzvahs, and an Irish wake or two.

If you do not intend on marriage but do intend on an extended-banging-warranty, it will still cause problems, severe discomfort, strain upon the friendship and possible erections lasting more than 3 hours. Oh wait, wrong small print, sorry. But yeah, eventually feelings will be hurt, someone will bring a date to the best friend’s family bash, and someone will be crushing up glass to put in someone else’s Tom Collins.

So, sure, it’s “OK” to bang the sibling, but just remember you’re not losing a best friend, you’re gaining an entire family intent on breaking your balls. Mazel Tov!

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