3 Important Reasons Not To Date Your Best Friend’s Sister

We men are hypocrites when it comes to our sisters or best friend’s sister. Maybe that is why we end up being insensitive parents to our adult daughters. You know how it is, fathers always hang a purity label on their daughters and God help the love-struck guy who dares challenge that notion.

best friend's sister

I come from a generation where we can say all sorts of things about girls. Every girl is fair game except our sisters. The unwritten rule is never to say anything disparaging about them. Even when complimenting our best friend’s sister, we have to chose our words carefully not to annoy our guy.

So from that sort of mindset, dating our best friend’s sister is just out of the question. Seriously, I never entertained the thought of my friends dating any of my sisters. The idea is so way out of my comfort zone.

I am sure my guys sneak admiring glances at my sisters. The important word there is ‘sneak’. I do it too. We just can’t let our friends know the direction of our thoughts where their sisters are concerned.

That was why I found it really startling when Skip, an old friend, told me he was going out with Tom’s sister. I was like, “What the bleep?! Does Tom know about it?” Skip smiled confidently and informed me sending messages to the girl through Tom was all part of the program.

Meaning Tom knew and was okay with it.

best friend's sisterI never looked at Tom the same way ever since. He must be a special breed of guy. I know his sister very well. I’ve had the usual guy fantasies about her because she was very beautiful. But I obeyed the rules and never let on to Tom about these thoughts.

But like they say, different strokes for different folks. But I felt cheated though. If only I knew Tom was that sort, it would have being a race to the finish line between Skip and I.

See why I told you we are hypocrites. I wouldn’t allow skip or Tom cast their useless eyes on any of my sisters. Somehow they knew it, but I can’t remember telling them.

Seriously, take a look at these scenarios and I dare you to tell me you don’t feel me.

Dicussing Guy things with your Best Friends

best friend's sisterThat is usually the bone of contention in our minds about dating your best friend’s sister: the things we talk about when we meet. Sure we rage about politicians. Wicked and irresponsible parents. Football.

And girls. Yes that is where the gist becomes colorful. The most envied dudes are the ones with the most adventurous stories to tell about their conquests and how they go about doing them. Stories like this are the bread and butter of our sit downs.

Now imagine if one of these friends is dating your sister? Would he have the guts the say the stuff he does privately with her in front of you? Hell no.

He won’t even have the cojones to talk about his going ons with his other side chicks. His contribution to this important segment of guys round table would be seriously limited to nods, smiles and pensive brooding.

You just can go around describing your best friend’s sister’s anatomy just like we do gleefully with other girls.

Visiting Your Best Friend’s Sister Or Him?

Okay, let’s assume you mange to do the unthinkable and date your best friend’s sister. Who are you going to hang out with when you go to the house? The friend? The sister? Both of them at the same time?

This is a very awkward situation. You know you can’t be free to express yourself in that position. Assuming you chose to ignore your girlfriend and focus on your best friend. You still feel pressure to be at your gentlemanly best with your bestie.

It’s just like visiting the in-laws which no man loves doing.

Your best friend is in the middle

best friend's sisterNo guy loves being in the middle of a fight between a bestie and his girlfriend (and in this case, your sister). By dating your best friend’s sister, you’ve done exactly that. Another unwritten guy rule is to always support your best friend in a fight with his girlfriend.

So who do you expect your best friend support? You or his sister? You are putting the poor dude in an impossible situation. The kind of situation that is likely to rip the family apart if it is not handle with tack.

Honestly, I know a situation like that would present the perfect opportunity to tell my best friend a few choice opinions. A serious kick in the butt is not ruled out I tell you.

Thankfully I’ve never found myself in any of the above scenarios for the simple reason that none of my friends have being stupid enough to date my sister. Neither have I dated my friends’ sisters before.

Have you being in a position like that before? Tell us all about how your handled yourself. Or just tell us your thoughts on the issue. The comments section below is a good place to start. We would also loved to hear you on Twitter or Facebook.

2 thoughts on “3 Important Reasons Not To Date Your Best Friend’s Sister”

  1. I told my friend his sister and I were dating and there’s nothing he can do about it, because , sometimes, all you need to do to get something done is be a cocky son of a bitch. His sister, who I am still dating, told him that his view doesn’t mean shit to her when he protested, and I’m no longer friends with him

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