I'm in a pickle

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grimgor42

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Mar 15, 2011
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I'm in my sophomore year of college, and the younger sister of one of my good friends is in the grade below me, lets call her "Sarah". She used to be involved with my best friend several years ago, where she ultimately rejected him several times, the short story with that is that he could not escape the friend zone. Anyway, not long after that my best friend moved to a different state, halfway across the U.S. and has been there for over a couple of years now. They still talk, and periodically she visits him, but he has NEVER been out of the friend zone with her.

Now since she is now at the same college as me, we have been hanging out more, and have developed an attraction for one another. It would be easy for me to initiate a relationship with her since she's dropping the usual hints, but I can't help but hesitate since I'm not entirely sure how my best friend will handle it. He's had girlfriends since he moved, and would not have trouble getting a new one, but I suspect he's been sabotaging his own relationships because he still pines for "Sarah" even though he never got out of the friend zone and only see's her once a year, if that. I'm also unsure how "Sarah's" brother or mother would react. I've been a friend of her family for a very long time and I'm sure her mother thinks well of me, but I'm not sure how her brother would feel about one of his oldest friends suddenly dating his sister.

So if you've read all of that, you must be pretty freakin bored, but since you're still here, would you mind giving your opinion on how I should proceed? I feel that "Sarah" likes me a lot, and I'm really starting to like her more, and I don't have anything else going for me romantically except my crazy ex still texting me. Would I be an asshole if I dated "Sarah"?
 

RemuValtrez

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Sep 14, 2011
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No, it would not make you an asshole. Just let your friend know, if he can't handle it then it's his fault. If you don't, then the feelings you have developed will continue to develop, and you'll get stuck in the friend zone as well along with your friend.
 

smithy_2045

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Jan 30, 2008
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It's not your problem. You'd be an asshole if you didn't tell him at all though.

RemuValtrez said:
No, it would not make you an asshole. Just let your friend know, if he can't handle it then it's his fault. If you don't, then the feelings you have developed will continue to develop, and you'll get stuck in the friend zone as well along with your friend.
You only "get stuck in the friend zone" if she isn't attracted to you.
 

RemuValtrez

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Sep 14, 2011
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smithy_2045 said:
It's not your problem. You'd be an asshole if you didn't tell him at all though.

RemuValtrez said:
No, it would not make you an asshole. Just let your friend know, if he can't handle it then it's his fault. If you don't, then the feelings you have developed will continue to develop, and you'll get stuck in the friend zone as well along with your friend.
You only "get stuck in the friend zone" if she isn't attracted to you.
Not true at all. I've been put in the friends zone after not taking the obvious opportunity to ask them out. More than one way to get stuck in that dreadful zone!
 

Acier

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Nov 5, 2009
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RemuValtrez said:
smithy_2045 said:
It's not your problem. You'd be an asshole if you didn't tell him at all though.

RemuValtrez said:
No, it would not make you an asshole. Just let your friend know, if he can't handle it then it's his fault. If you don't, then the feelings you have developed will continue to develop, and you'll get stuck in the friend zone as well along with your friend.
You only "get stuck in the friend zone" if she isn't attracted to you.
Not true at all. I've been put in the friends zone after not taking the obvious opportunity to ask them out. More than one way to get stuck in that dreadful zone!
Not true at all. It doesn't exist. I shouldn't have to hear my personal preferences justified by this bullshit. Deal.


OT: Go for it, not your fault she didn't find him hot. And if he throws a hissy fit, then well, he's just not very mature and shouldn't really be in serious relationships anyways.
 

Slash Dementia

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Apr 6, 2009
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You're doing nothing wrong. Not with "Sarah's" brother, and not with your friend. Maybe speak to both brother and friend before your next move. Or talk to Sarah and see how she feels and what she'd think. There's nothing wrong with this at all--just go for it.
 

Fawcks

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May 10, 2010
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Careful, you may already be in the twil- I mean, FRIEND zone without realizing it!

Women dropping hints generally means nothing.
 

Lvl85Humanoid

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Oct 3, 2011
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Life is short and fortune favors the bold. Go for it, and let the pieces fall where they may.

This chick could be really special for you, and your friend would be an asshole to get in the way.
 

Evelynia

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Jul 18, 2011
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I'd say go for it, although it's not a bad idea to talk to the guys involved first. If they're not cool with it it still isn't really your problem, but at least you had the courtesy to bring it up first. You and 'Sarah' are both adults, and if you like each other it isn't really anybody else's business.