TJ's Dating Hub

To Date or Not to Date? Your Buddy's Sister

Wow, you’ve actually decided to tread on the often forbidden land between brotherhood and dating. That’s a very bold move, I must say. Very, very bold. After all, this isn’t something you do for fun or you’ll risk losing a friend and gaining an enemy for life.

If it's any consolation, this isn't just a guy problem. The risk of losing friends by dating their family members runs true for everyone.

The thing about dating your friend’s sister is always the tug of forces on opposite poles: valuing your friendship or going after the girl you like. It is a very, very tricky situation and it mostly depends on the kind of brother your friend is.

Blood is Thicker Than Water

your friends sisters

Is that scary or what? It's not meant to scare you. It's more of a brotherly advice to think about this really really hard first before plunging in it. That cliche is not there for nothing.

See, there are different types of brothers in the world. Or should we say, there are different types of people that brothers become when their friends start pursuing their sisters. Let’s take a look:

  • All-out supportive bro – You’re lucky if you’re buddy is like this. He takes to heart his new role in life: your sidekick. He will give great words about you and he will set you guys up on dates; he will even invite you over at home more often than usual just so you and sissy can see each other ‘unintentionally’. Sure, unintentionally. And if things don’t work out between you and his sister, you guys will stay friends.

  • The Silent Killer – He won’t say anything about you and his sister dating, but the moment you express your intention, he will try to distract you. He will make you meet all of his hottest lady friends and cousins and co-workers just to veer your attention away from your sister. But if anything, he does not badmouth you to his sister.

  • The Cool Cucumber – Nada. Shiz. No word. At all. He does not care and does not at all take it personally. But watch it man, he is secretly taking note of everything you’re doing and waiting for your big bad move. He’s still your buddy though. Chill..

  • The I-Will-Kill-You-Two-Times – Friendship is over the moment you show interest on his sister. I think that says it all. Start learning and relearning your prayers son.

TJ's Tips on How to Ace Dating Your Buddy's Sister

So, okay, you decide to go for it. Of course, no matter what kind of brother your buddy is, how you act around him and how you treat his sister will make a difference.

Here are some tips that you can use for whatever type of brother your buddy turns out to be:

  • Do not suck up to him. Seriously man, don’t. A guy who kisses people’s bums is undeserving of respect. Keep your dignity – don’t go as far as cleaning his own room just so you get his approval. You are dating his sister, not him.

  • Try to be as normal as possible. If you’re friends with any family of the girl you’re dating, chances are you become mushy around them and you try your best to impress them. Don’t. Don’t talk about her to him randomly, it would just make things really awwwwkkkkwwwaaarrrddd!!!

  • Earn their respect. Your friends are the people who know you best outside of your family. They know your weaknesses, follies, and behavior around women. If your history on women – that they know so well – do not meet their standards, the best you can do is show them that you won’t do that to their sister..

  • Talk to your friend man-to-man. You will need to face that one awkward situation to talk about ‘the situation’ (no relation to the Jersey Shore dude, I promise). Be honest, be a man.

Love vs. Lust

Note: Flings don’t count as dating. And buddies’ sisters should not be in the black book either. If you play your cards right, you’ll have a girlfriend and her brother as your best friend. If not, you’ll lose both.

-TJ