When Is It O.K. to Bang Your Best Friend’s Sister? Plus Other Quizzical Nonsense

By 08.07.12

Q: You're a D-1 college bro. Your teammate has a hot sister at your school, his twin in fact. He's one of your best friends. Do you pursue or let this one fly?

A: Does he think you’re a raging scumbag that probably has HPV all over your dick and inside your throat? If so, he’s not going to be cool with you chasing his sister. He’s fine with “you doin’ you” all over other chicks' faces, but not his sister’s. However, if he thinks you’re a decent person — not just a male whore and party animal extraordinaire — then he might be fine with you trying to date his sister, as long as he’s not some over-protective weirdo.

Your biggest hurdle is that he knows you; you aren’t some stranger that hasn’t told him about all the ways you’ve disgraced random chicks. So feel him out and even mention dating his sister (almost jokingly), but definitely don’t do anything if you can tell he’s against it. That’ll only end with a bottle broken over your head. Trust me, I’ve crossed that line.

Q: I was dating this girl for over a year, she was the sh*t, cool and down to earth. I decided to go abroad and leave her for the semester. We decided to break up and see what happens down the line. We made a pack that we wouldn't ask one another what was going on. I never lied once to this girl and she popped the question if I was f*cking anyone. Needless to say her sorority sisters were on my trip who were cool as f%ck but the ex-girlfriend cracked and asked them what was going on when we decided to call it quits for the time being due to whole distance and seeing other people. She finds out everything leading up to that, that I'm banging girls, getting hammered and fratting hard. When I got home we were still kind of talking but I had a two women rotation going on before I left for a job in LA. She later asks me if I ever hooked up with someone in her sorority… She knew the answer and one of her sorority sisters told her who wasn't even in the same place. I haven't talked to her since and I am sure she is seeing someone which is cool. I let her go, I'm in LA a place where pu$$Y is all over. My question ultimately is how do I tell her the truth about everything leading up to her not talking to me? She is the shit but she changed and I'm sure her friends are filling her head with all this bull$hit that I'm a terrible person etc… How do I approach her and do I come clean about everything that has happened in the last 7 months?

A: Confessing all your sins is NOT the way to go. Nothing beneficial will come of it. You'll feel better about yourself — which seems impossible given all the ass you claim to be slayin'– but her fantastical perception of you being a “good guy” is already forever tainted, if not altogether gone. She knows you're a sexual deviant, so why throw logs on the fire by putting names and faces out there?

The moment you tell her that you stuck it to one of her friends, that image will implant itself in her brain forever. Every time she tries to feel something for you she'll stop herself, remembering you went base deep into that back-stabbing, slut Hilary (let's face it, most Hilary's yearn insatiably for dick).

What I'm saying is: confessing is NOT WORTH IT. Reiterate the pact you two had, and tell her she should start respecting it. Get fired up about it, too. You're the victim here.

Q: Is it wrong of me to look down at chicks who tell me they want to become elementary school teachers?

A: When I was in college I had a similar why-would-anyone-want-to-become-a-poor-teacher attitude. Thought they were fools. Invalids, really. Then I left college and took a job in finance for the sake of getting a job in finance and MONEY.  (God, do I love money. If paper cuts weren't a factor I'd jerk off with it.) Only I hated finance and, most days, living. So you could say I've had a change of heart.

Honest piece of advice, don't knock people for living their lives they way they want to live them. I'd need a stadium of hands to count how many times people told me to go back to finance. To suffer doing something I vehemently loathed because I was making good money. “Don't you want to retire” they'd say. Yeah, retiring sounds nice –play some golf, maybe go to elderly fishbowl swinger parties — but I'd much rather want to wake up for the next 30 years.

And who knows, maybe these chicks that sinfully only aspire to teach will go on to write best selling children's books or find a way to revolutionize duck-duck-goose and make MILLIONS while you spend your days listening to old Nirvana albums thinking about the gigantic mess you'd like to leave for CSI. You just don't know.

Q: You have survived a crash landing on an unchartered island, deep in the Pacific ocean. You wander for days hungry, thirsty and about to collapse, until you finally see other humans. Through hand signs and body language, you come to the conclusion that they will provide food, water and shelter. You also notice that there are not any chicks around, all of the men are looking at your butt and they all seem to have boners. Do you, A – Gorge yourself with food and allow your poophole to be the main dessert for all of them. B – Turn and run for the hills, even though you are so weak they would probably catch you anyway. C – Pick the guy with the smallest dick, dye your hair blond and promise your love until the day you die, as long as he doesn't share you with the others.

A: I hope that when your mom would brag to all the other mothers about “how creative” her son was — because every mom does that — that this was what she had in mind.

I'm begging you, can there be a choice D whereby I eat a bunch of used band-aides out of an overweight girl's vagina in exchange for some Saltines so that I'm not raped anyway you cut this? No? Prick.

Since I have to go strictly with the info you provided, I'm going to take my chances and keep my dignity with B. Let them catch, rape, and hopefully kill me. No way I’m giving it up for free or becoming a whore for food. Now, I'd have picked A and tried to run when I was fueled-up but you claim my assh*le is required to stick around for dessert, so thanks, but I'll pass. And I can see how C also might sound tempting but I'd still rather be dead than spend the rest of my life as a blonde. Huh?!?

Q: When visiting my cousin at his school about an hour from mine, I saw a girl at a bar that goes to my college, we had seen each other before and made awkward eye contact but never talked. So with my blood flowing with liquid confidence I make the first move and buy her a drink. One thing led to another and we ended up going back to her friends house to do the lords work. And let me tell you, this girl is spicy hot, so I kinda want to get this to continue, at least for one more hook. When I'm back at my college the next weekend I shoot her a fairly neutral text and ask her what’s up, and receive no response. My school is small and there’s only really like 4 or 5 good party bars so you usually always see roughly the same crowd every night, and low and behold I see her at the very first bar I get to, and this is where things got kinda strange. I didn't go up to her right away and barrage her with questions cuz that’s not my style but passing her walking through the crowd I spoke to her and she definitely heard me and completely ignored me. This has been the trend, anytime I go to visit my cousin at his college, she happens to go up there too and wants to bone righteously, back at my school I completely don't exist to her. So I guess I'm wondering what advice you would have to get her in bed when I'm at my college and not have to drive a hundred miles anytime I want to bone her. Much appreciated, Bro.

A: Well, that's peculiar.

Since she won't text you back or acknowledge your existence on your own campus, your best opening to ask her something is right after you f*ck the living daylights out of her at your cousin's school. Then again, if you were f*cking the living daylights out of her you probably would be in this predicament to begin with.

Hate to admit it, but there is something about you that she doesn't like or something that’s living in her own closet that’s keeping her from acting like a normal human being.

Q: Okay, so during the fall semester I got really involved with this cute girl. Let's call her Fall Ball. No relationships just constant hooking up and sleeping over. We were getting very close but nothing was going to come of it, for now at least. We left on good terms as she went abroad in the spring and I was quite the good kid. Didn't even touch another girl for a solid 3 months, but the last two weeks of the semester I got myself into a bit of a situation. I met a girl, let's call her Spring Fever, who I was suppose to help get with my friend, but it wound up being me she liked and wanted to get to know more. Anyways, we wound up hooking up and Fall Ball found out, by who other then one of her best friends. What sucks here is that the 2 girls have a mutual friend who found out and basically f*cked me. Anyways, things with Spring Fever are good, but Fall Ball pretty much can't stand my existence, and I kinda don't blame her. Any advice on how to not make it awkward when I see her on campus?

A: DUDE! You’ve got this all wrong. Sh*t’s gone awry in your head. This is 100% NOT ON YOU. Fall Ball left you and your uncommitted hook-up situation for a semester abroad. If she wanted to be your girlfriend she should have spoken up and locked you in prior to leaving. So blame her for not being able to stand your existence. Blame the sh*t out of her, in fact. Remind her that SHE LEFT YOU and you were well within your rights to get some Spring Fever. The only thing I can see that you’ve done wrong is not get f*cked earlier. A 3-month self-imposed dry spell when you’re not in a relationship? That’s egregious.

The easy thing to do is keep it awkward. Why do you need to explain yourself? You like Spring better than Fall, who doesn’t? But if you run into Fall Ball constantly, it’s better to just break the awkwardness. So give an Oscar-winning performance. Other than noting the whole “WE WEREN'T IN A RELATIONSHIP” thing, fill her up with bullsh*t; you know what she wants to hear. Tell her how much you liked her, how you wish the circumstances were different, and then admit to f*cking up a good thing with her but the moment she's like “Yeah, you did, Seth” drop the bomb that when you met Spring Fever you just fell for her and that you might be in love. That's probably not true but she'll certainly have no comeback and it'll crush her — make her think how she spent months letting you cover her in dick yolk while you felt nothing for her the entire time. Plus, in some sick way, she'll probably be happy that you found love…Or she'll hate your f*cking guts and the situation will stay as awkward as ever. 

Follow me on Twitter @JCamm_ and submit your Ask a Bro quesitons here.

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