I Slept With My Bro’s Girlfriend Before They Started Dating. Do I Tell Him?


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Q: So one of my best friends recently started dating a chick. He’s really into her and he likes her a lot…The thing is, I already hooked up with her. At the time I didn’t even tell him because it could get kinda awkward and I didn’t want people to know…Am I supposed to tell him and look like a complete dick or just let him live in bliss?

A: Welp…I won’t say this isn’t a tricky one. When it comes to crossing swords, double-dipping, etc, you can really only gauge reactions on a case-by-case basis.

I’ve had friends male and female who actually think it’s funny when they hook up with the same people. Lit sit, and discuss, and laugh about the whole thing.

On the other side I know people who have actively cut off contact as a direct result of what they would most definitely refer to as a betrayal.

You know the guy better than I do, so try to anticipate his reaction before provoking it. If you think he’d want to know, you owe it to him as a friend to tell him.

If you genuinely believe telling him would actually just make it a whole lot worse, vow to yourself that you will at no point breach the topic unless he asks you directly.

At which point you respond in a matter-of-fact way so he can’t blow it out of proportion and go all drama queen on your ass.

Damage control, from either perspective, is absolutely necessary.

Q: What is the most awkwardest/shameful thing you’ve had happen? I once was with a girl who bit my neck one to many times, the next day my friends asked me if I was attacked by a werewolf/vampire. I had to wear a hoodie for a week.

A: Allow me to kick off this question by addressing what contest you most definitely did not win, the spelling bee.

Now that we’ve established that, I also have to point out that awkward and shameful fall into two very different categories for me.

An awkward occurrence is momentarily uncomfortable but in the end will probably provide a decent chuckle.

Awkward, for me, is when your best friend walks in on you making out with her brother. It happens. It feels weird. But you don’t regret it.

Shame on the other hand, is almost always attached to a feeling of regret. Shame comes about when you’re 17 gin and tonics deep at your best friends bachelorette party, and suddenly gain consciousness while making out with a foreigner–apparently forgetting that you too are in a committed relationship.

That’s some shameful fucking shit. And when paired with a whopping hangover, can be the most lethal of sufferings.

So ultimately I’ll always prefer to regale an awkward tale rather than a shameful one; and as for which category yours falls under, I’d have to say the latter.

Q: I have one big problem. I am considered fairly good looking, have a good body, but the thing that kills my confidence is the size of my package. Every time I get close enough to sleep with a girl, I bail. How small is too small?

A: A big problem with a tiny body part? If you’re asking the question, you already know the answer.

That said if you don’t try, you won’t know.


Q: I’m a guy on the husky side. I’m nice, chill, can hold an interesting conversation, and show a girl a good (platonic) time, but none of that seems to be getting me anywhere. As a babe, do girls try to stay away from huskier guys in college or is being nice not the best approach? Should I just suck it up and wait until I shed the rest of the weight or is there something else I could be doing to interest girls in the meantime?

A: Listen Sir Husky. God knows I appreciate a good-natured man who can purportedly show a girl a good time. I mean, I’m human for gods sake.

But if I were you, I’d be asking a lot fewer questions and doing a lot more push-ups.

It’s the sad truth of our shallow culture but as with dudes, chicks want a guy who is fit, or at least visually pleasing.

As a dude, you have an even better shot at getting skinny by slightly altering your caloric intake and doing a little cardio with your weights.

No offense but it’s not that fucking hard.

And I mean, why wait it out? If you “suck it up and wait”, praying for the pounds to melt off your body like butter without any active effort, you’re just going to continue missing chances with babes.

For your sake I think anything is worth the effort if it means getting out of this self-proclaimed “platonic zone”.

Is that more harsh than friend zone or slightly less offensive? Hard to say. But I like it.

Q: Babe, I’m a college cheerleader at a big D1 school. It’s funny, with pretty much any girl I go after at school I get with ease (not even trying to sound like a dick), but when it comes to this one girl on my team who I actually would adore to go out with, I am not really sure how to play it.The whole team dynamic has me uneasy, so babe, how do I go about getting this girl without alienating myself, or her, from the team?

A: Just…so we’re clear here. You’re a male cheerleader? Under the guise of a straight dude?

There’s a first time for everything, I guess. Though I’m not sure how that plays into the timeline of you getting laid.

So yes, I agree that it’s funny you get laid with any girl at school, because it makes me wonder where the fuck you go to school.

No matter, I won’t Cheer Bash you for the hell of it. At least not this early in the week.

I get the story.

You like a chick, but it’s c-o-m-p-l-i-c-a-t-e-d.

You can’t be sticking your hands up her skirt mid-shoulder stand without other members of the team becoming suspicious and/or jealous. And god knows you don’t want to compromise the future of your cheereer. You’ve got another good, what—year and a half left of that?

Alright, I tried. From the sounds of it I think you’ll figure it out.

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