Ask A Hottie: I Accidentally Slept With My Step-Sister’s Boyfriend…Twice??

Welcome to “Ask A Hottie,” Break’s weekly column in which a plethora of idiots ask one single idiot what they’re doing wrong with their lives. In reality, the lone idiot should be writing to others for help, but where’s the fun in that? Also, the self-help questions I have aren’t fun. They’re more along the lines of “Will Windex get purple hair dye out of a granite sink” (it’s the only cleaning product we have and we’re too cheap to buy something new) and “Will eating laxatives make you skinny?” The answer to both is a resounding “No.”

No really — how do I get this hair color out of my furniture?

Q: My step-sister and I have not always had the best relationship. We were never mean, but we were never super nice to each other either. She is eight years older than me and because of this we didn’t have much in common, but after her mom (my step-mom) contracted Alzheimer’s she began to reach out and we became close.

It’s been a few weeks of us being actual “friends” with each other and she confided in me that she believes her boyfriend is cheating on her. He works at the Starbucks I visit frequently, and she asked me to watch out to see if there are any girls he pays extra attention to.

It turns out that the first day I’m supposed to be “on the lookout,” one of my guy friends walks in and starts chatting with the boyfriend. I walk up to say hello and wind up joining their conversation. From that point on, I’ve always been invited to hang out with my step-sister’s boyfriend and his friends, since we know a lot of people in common. I never told my step-sister, because even though I was having fun I knew it was wrong.

Then, a few nights ago I was having dinner with friends and he saw me out on the town. I’m not old enough to drink yet, so he snuck me into the bar he and his friends were at. One thing led to another and we ended up sleeping together. I felt awful.

Last night I texted him that we needed to talk. We met at his place and I told him what happened was wrong. He agreed, but we wound up having sex again.

This is the closest I’ve ever been to my step-sister but I really like her boyfriend…what do I do?

A: Stop thinking with your vagina and start thinking with your brain for starters.

There’s so much “WTF” thought processing here I’m not sure where to jump in. Your step-sister asks you to keep an eye on her boyfriend while he’s at work because she’s afraid he’s cheating on her, and your immediate answer is “Ok, but what if I’m the one sucking his dick? That’s ok, right?”

You, at starbucks, being a giant hoebag.

Is there even a point in me continuing? You know this is fucked up. You even said way back in the beginning of your question that you made sure not to tell your step-sister that you’d been invited into her boyfriend’s inner circle of friends because you knew hanging out with them was wrong. Yet here you are, trying to fill the guilt-ridden hole in your soul with the dick the drilled the hole there in the first place. You say your sister is eight years older than you, so I hope for your sake you’re only 17 or 18 because any more and you’re a straight-up piece of shit; younger and her boyfriend is a pedophile; same age and you’re just a dipshit. For your sake, we’re going to stick with dipshit.

“Dipshit” isn’t the same as “innocent” though. It’d be one thing if you banged her boyfriend and then cut it off for good – you’re still a dipshit in that case, but at least you have a conscience and aren’t one of the most selfish people in the world. But in the words of Billy Mays…

Because you didn’t bang him once, you banged him TWICE. That’s a second time you thought to yourself “This is definitely one of the worst things I have ever done” as you stroked the shaft and licked the rod, followed by “Oh em gee I just feel SO bad” when you left his house and texted him some flirty bullshit with a bunch of 😉 faces. You obviously do NOT feel that bad, otherwise you wouldn’t have done it a second time. I broke my leg when I was five and it felt like shit, you don’t see me jumping into murky water without verifying how deep it is anymore, do you? Nah, because it actually felt bad and I didn’t enjoy it. You, clearly, enjoy fucking your step-sister’s boyfriend and don’t feel bad about it.

Also, hate to break it to you sweetie but he’s not going to dump your sister for you. I don’t care if you “really” like him or think he’s the “one” or just get your panties all moist at the idea of an older guy paying attention to you – to him, you’re just a damp hole to anger-screw whenever his girlfriend pisses him off. This guy doesn’t like you – he’s a cheater. And that should be enough for you to not like him either, because what kind of self-respecting girl sticks around and patiently waits to be upgraded from sidepiece to bottom bitch? You, apparently.

You need to tell your step-sister what’s been going on. It’s going to suck and destroy your relationship with her, but moving forward and not saying anything is going to make it even worse. Think of it this way: you’ve banged him twice, feel awful and come clean. Your step-sister hates you, but you did the right thing. Maybe one day things can be repaired.


You’ve banged him 10+ times and don’t come clean. Your step-sister finds your panties, homework, credit card, WHATEVER in his apartment, or maybe one of her friends sees the two of you out and tells her because it’s suspicious – the point is, she finds out about what’s been happening without you telling her. Your entire family now thinks you’re a home wrecker, and I can’t say they’re wrong. No one can, in fact, because you are.

It may not read like much, but there’s a giant difference between coming clean on your own and getting caught in a lie. The third option, of course, is to cut everything off and swear the boyfriend to secrecy, but in that case you’re still a piece of shit because the chances that you’re the only idiot this guy has cheated on your step-sister with are slim. In the end it’s up to you, but the only question I have to leave you with is this:

If you were the step-sister and she were you…which option would you want her to pick?

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