You’ve known her since you were a pubescent boy and you’ve always sensed an attraction, but never acted on it.
Even though she was totally off limits, your hormones couldn’t be controlled and you probably ended up talking about her daily at high school lunch tables and, eventually, outside of parties while smoking cigarettes with your boys.
Of course, we’re talking about your friend’s sister — the holy grail of snatch, assuming she’s above a 7.
Although the closest you’ve ever been to getting involved with her sexually is keeping a mental image of her in your spank bank, it doesn’t mean the opportunity is completely lost.
In fact, as time has passed, you’ve grown and matured and she may see you in a totally different light — you’re no longer that scrawny dweeb drooling over her ass in yoga pants.
OK fine, maybe you still are drooling over her, but here’s a guide to understanding why making a move on your friend’s sister may not be as big of a deal as it once seemed:
You’ve always joked around about how hot she is so your friend has to be well aware of the fact that he’s the bro in the group with the hot sister. In a high school, he probably took offense to it, pouted like a little schoolgirl and swore to fight anyone who laid a hand on her.
Although he’s probably going to be sore about you making a pass at her now, he’s not going to hold it over your head for more than a few minutes and there won’t be any physical altercation, or at least I hope there’s not.
In most cases, bros should be able to laugh about this kind of stuff if they’re in college or in their mid-20s. The time to get pissy about protecting your sister has long passed. As long as it’s just you making a move and her shooting you down — more than likely the result I hate to break it to you fellas, then it can be played off as something completely innocent and everyone in the room can laugh about it.
Would you do her if she were willing? Of course, but that’s not the point here.
What better time to hit on your friend’s sister and let her know how you’ve always felt about her then when she has a boyfriend? This play is beneficial in several ways. First, if the boyfriend gets pissy, your friend can have your back and let him know you were just kidding — no harm, no foul. It’s also worth noting that none of the potential drama between you and your friend that we discussed in reason No. 1 will come about because you can, once again, sell it as a joke.
Another good reason to hit on her when she’s “unavailable” is that it shows you have confidence and ambition — not every guy would make a move on a girl who he knows is taken. She’ll like that and remember it.
Lastly, and looking at it from a more long-term perspective, she’ll be thinking about you making a move on her long after it happens — and much longer than her boyfriend would like her to think about it, and she’ll always have it in the back of her mind. She may never tell you she has reciprocal feelings, but if she thinks about it long enough, who really knows what she might start thinking? Women have weird brains.
Eighteen is fair game as long as you haven’t entered the age where you should have a wife and maybe a kid, if not at the very least a fiancé (I’m talking about guys in their 30s).
With that said, have some standards and don’t believe a complete savage. If you’re a bro who’s let’s say 24, then 18 is still fine, but don’t dip your hand too far into the cookie jar because you might end up with a Girl Scout cookie that hasn’t matured yet and then you’ll have some real problems on your hands.
Obviously, if you’re 20 you can hit on pretty much any chick that’s a junior in high school and above and still be fine — what an age to be! All you have to remember is that your friend’s sister is no different than any other girl you’ve approached at a bar. You may know a lot about her, but you’ve got to look at her as a stranger. The minute she’s put up on a pedestal, it’s all over. She’ll sense that boyhood fear and crush you with it.
Out of Town
It’s going to sound like a complete dick move, I know, but there’s no better time to approach a friend’s sister when she’s outside her comfort zone in a new city, or in a new place, without any of her friends. This works exceptionally well if she’s visiting your friend, her brother, and you two are her only allies in a 100-mile radius. Chances are your buddy will leave you at some point in the night to go chase tail and that will leave you with an open window. Take advantage of her vulnerability now or you mine as well never make a move.
The Golden Rule
This doesn’t apply to every bro and every circumstance, but the Golden Rule — the rule of reciprocation — should be valued high on this list. If your bro has ever made a move on your sister or even joked about how hot he finds her, then his sister is open and fair game and there should be absolutely no confrontation regardless of whether or not your successful in your attempt.
I feel like this one goes without saying, but I also feel obligated to list it off here so bros everywhere know that once the line has been crossed, there’s no going back. It’s a two-way street, by the way. If you’re the one who opens fire and hits on his sister, then you’re leaving him the option to go do the same to your sister.
We went over the visiting/out of town scenario, but there’s more than just one setting where hitting on your friend’s sister is a good idea, and quite possibility the only time such a move will work.
Those settings include: weddings, birthdays, reunions, holiday parties, and vacations.
Basically, any time when there’s alcohol and a celebration involved.
You have to remember: after high school and/or college, the number of interactions you have with this girl are going to be few and far between, so take advantage of every opportunity you get because life’s too short and by the time you see her next, you may be in a committed relationship with your bachelor days far behind you. If you aren’t, chances are she will be.
“Not Just Another Notch In the Old Belt”
She’s not going to be just another notch in the old belt. You know her too well and have known her for too long to just discard her and treat her like shit if you indeed end up sleeping with her. The moment will have some sort of additional meaning other than the boast of, “yea, I banged my friend’s sister last night.” Sure, it’s a great accomplishment, but it’s different than bringing home some random bird from the bar.
Freedom of Expression
As I already mentioned, the chances you end up bringing home your friend’s sister are pretty slim, but it’s still worth it to just let it out and express how you feel about her rather than suppress it. Keeping things inside is what psychopaths do.
You’re not a psychopath; you’re a healthy, All-American bro. Don’t let your old attraction to your buddy’s sister weigh on your mind too heavily. Once you’ve released it and let her hear all about it, you’ll feel a lot better and can just move on from it. Your friend will understand why you did it, because he’s a guy and not a chick.
Whenever you’re talking about hitting on a friend’s sister, the parents have to be brought up because there’s a good chance they know you pretty well and may or may not approve of you hitting on, or even taking out, their daughter.
Regardless of their opinion, you should be able to make a lot cleaner move on her now than you would have when you were a senior in high school or freshman in college, because you both are living out of the house and are grown adults who can make their own decisions. If her parents don’t like it, then that’s too bad for them; I’m sure you’re not the first guy to bring home their daughter.
If you’re getting, or have ever gotten, a sense of mutual attraction, then making a play on your friend’s sister is simply acting on your nature as a human and you are at no fault. Can your bro really expect you not to make a move if she’s giving you the signs? Sounds pretty unreasonable to me.
I’m well aware there are certain binding rules of relationships — marriage being one of them — that constrict some desires from ever being fulfilled, but if you’re single and she’s single too and you’re both hot for one another, then why even hesitate? You’re human beings, go fuck each other’s brains out.