Dating a friend's sister

[airblaster503]

Alright, never thought I would post in this thread. So one of my best friends sisters has been coming onto me lately, she is dating material I guess you could say, but the fact she is my friends sister has me at a loss and I am not sure if I should pursue or not.

 

[mm84321]

Originally Posted by airblaster503

Alright, never thought I would post in this thread. So one of my best friends sisters has been coming onto me lately, she is dating material I guess you could say, but the fact she is my friends sister has me at a loss and I am not sure if I should pursue or not.
I went through the exact same scenario. It drove me crazy for years. At first, I had no feelings for her, then after a while I started experiencing them. It was made even more awkward by the fact that I was close with the whole family and used to spend a lot of time at their house. Never truly resolved the situation. Sorry I can't help you out.

 

[HgaleK]

Originally Posted by airblaster503

Alright, never thought I would post in this thread. So one of my best friends sisters has been coming onto me lately, she is dating material I guess you could say, but the fact she is my friends sister has me at a loss and I am not sure if I should pursue or not.
If you value his friendship, either drop it or fill him in on the situation and ask for his blessing. If he says no, then respect it and drop it. There are a few of my friends that I would happily let date my sister if she was old enough. There are plenty who I wouldn't let near as well. If you're the sort of guy that he would want to be dating her, then he may well say yes. There's something to be said for having a known entity dating family over a stranger. Granted, he may also freak out on you for even considering tapping that. Use your judgement here

 

[Matt]

ooh...this is a much more interesting dilemma. I am abusing mod privileges and dragging it out into its own thread (since I figure half of SF wrote this thread off as a lost cause on page 2)

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edit: ok done.

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My thoughts, basically I think you almost have to be ready to lose the friend for the girl at some point.

I mean, first of all, I think you have to go to the guy and kind of seek his blessing. "Dude, I kind of like your sister man, but you're one of my friends, and I'd feel weird asking her out without you knowing."

Then you may have to forgo a lot of the pleasures of boy-dom, as the relationship is kind of changed from here on. Coke induced bachelor party frivolities with the strippers get looked on none-too-kindly when you cease to be 'my boy' and commence a career as 'my sister's boyfriend'. God forbid you get caught cheating.

And then...what if it ends? Awkwardness highly likely to ensue post breakup. They will always be Brother N Sister.

Anyhow, FWIW everything I posted above is theoretical. I've never dated a friend's sister...thoughts from the gallery?

 

[mm84321]

Originally Posted by Matt

My thoughts, basically I think you almost have to be ready to lose the friend for the girl at some point.
It's pretty funny; being someone's close friend for a matter of half a decade seems to not weigh as heavily as you'd think when considering which you'd rather pursue: continued friendship, or the sister.

 

[airblaster503]

Whoa, didn't expect this to be made into it's own topic.

Originally Posted by Matt

ooh...this is a much more interesting dilemma. I am abusing mod privileges and dragging it out into its own thread (since I figure half of SF wrote this thread off as a lost cause on page 2)

--

edit: ok done.

--

My thoughts, basically I think you almost have to be ready to lose the friend for the girl at some point.

I mean, first of all, I think you have to go to the guy and kind of seek his blessing. "Dude, I kind of like your sister man, but you're one of my friends, and I'd feel weird asking her out without you knowing."

Then you may have to forgo a lot of the pleasures of boy-dom, as the relationship is kind of changed from here on. Coke induced bachelor party frivolities with the strippers get looked on none-too-kindly when you cease to be 'my boy' and commence a career as 'my sister's boyfriend'. God forbid you get caught cheating.

And then...what if it ends? Awkwardness highly likely to ensue post breakup. They will always be Brother N Sister.

Anyhow, FWIW everything I posted above is theoretical. I've never dated a friend's sister...thoughts from the gallery?

That is the biggest problem in the decision for me, the awkwardness of a breakup. I know he would give me his blessing to date her, but I am not so sure it would work out in the long term.

Originally Posted by mm84321

It's pretty funny; being someone's close friend for a matter of half a decade seems to not weigh as heavily as you'd think when considering which you'd rather pursue: continued friendship, or the sister.

There is a large part of me that just wants to say ******* though and go for it. I mean she is a good girl with a pretty good personality, but I am not even going to lie, she has a sweet body and I want to tap that ass.

I guess I should also say we have somewhat messed around previously, nothing more than making out and some wandering hands but I backed off after that just because I didn't want things to get awkward. May post updates in the thread soon, since there is at the least a probability of something happening while under the influence. Until then all advice is much appreciated.

 

[Mr. White]

Since when did you care about the brother of any other gal you dated? Point, set, match.

 

[alexanduh]

seeing as you nkow the family and spend a lot of time at their place its gonna be mega awkward when you break up lol. if you go for it youre going to have to stick with it for the rest of your life. the friend will probs kill ya for breaking her heart.

 

[Matt]

Originally Posted by Mr. White

Since when did you care about the brother of any other gal you dated? Point, set, match.

you don't have a lot of friends huh?

 

[Thomas]

Originally Posted by Matt

you don't have a lot of friends huh?

my thoughts exactly.

 

[clee1982]

if it works out great, if it doesn't work out, I am sure friendship will be repaired at certain point, but can be quite long down the line. Do you stay on good term with your ex. in general? I mean if you stay on good term with her after break up, then I think something is probably still salvageable between you and that entire family.

Side story, one of my best buddy dated one of his best friend's sister. Not just some random ones, the guys have been friends since like elementary school. He knew his sister and entire family for a long time as well. Anyway, things didn't work out (semi-cheating from her side, while he was in a hospital after car accident), so now things are just well... a bit funny. They're still good friends from what I can gather, but things are never the same if you ask me.

 

[intent]

Are you sure she's even into you? You'd look pretty stupid if you end up with neither the friend nor the sister.

 

[Hombre Secreto]

Are you really that desperate? Sounds like you only want the ***** and nothing more. If that's the case why mess with your boy's sister? Plenty of hoes out there that won't potentially destroy a friendship.

 

[CCH]

Or you might date her for a couple of years fall in love and she cheats on you and break up, then your friend ask you to go over to his place to hang out, and you have act like a bigger man and act all ok infront of his family.

 

[globetrotter]

I had a few chances like this when I was younger and chose not to pursue it. in the global scheme of things I still have the friend and I am sure I wouldn't have ended up married to the girl. on the other hand, I had a lot less sex than I would have liked when younger. if I were doing this again, I don't know that I wouldn't have tried for the girl.