jayaway Posted November 11, 2016 Posted November 11, 2016 Hi All, So a little about me. I currently have feelings for my best friend of 10 years sister. This feeling has been going on for about a month now and I have yet to tell anyone. I am unsure if I should act on these feelings or just let them subside. I've known her for a long time, but we don't really talk to each other aside from the greetings every time I see her. I just so happen to saw her at a party about a month ago and we conversed a bit. I am actually really curious to get to know her more. In all honestly, what I want most right now is to get to know her more and to see whether or not we're compatible. The last thing I would want to do is to make things awkward between me, her and my friend. At the end of the day, if I find that we're not compatible, at least I got to get to know her better. How should I go about this? To be frank, I am a bit intimidated from starting a conversation with her. Like I said earlier, I wouldn't want to make it awkward between me and my best friend.
spiderowl Posted November 11, 2016 Posted November 11, 2016 It's likely to be awkward between you and your best friend if you date his sister, but if you like the girl then you need to decide which is ultimately most important to you - a chance with her or your best friend's comfort. He may still be your best friend while you are dating her. On the other hand, he might flip. Just be prepared for whatever reaction, let him talk/grumble/whatever and then wait and see how he feels when he has adjusted to the news. Should you tell him before trying to get to know her or ask her out, or should you wait until you have asked her out? Probably best to say you are going to ask her out or are interested in doing so in such a way that he can't interpret it as asking his permission. If it appears you are asking permission, he could say no and then where would you be? You're a grown up now, you need to determine what matters to you in life and go for it. 1
smackie9 Posted November 11, 2016 Posted November 11, 2016 Well most would recommend you talk to your friend first and see how he feels about you having an interest in his sister. This will save you from making things too awkward. I say go for it and TBH it's not as a big deal as you think. You will be OK. Go into this with confidence
Author jayaway Posted November 11, 2016 Author Posted November 11, 2016 I feel we are old enough to make our own decisions. I don't want to keep him in the dark forever, but when/if I do ask his sister out as in date her, I do intend to let him know. For now I guess I want to just get to know her, doesn't have to be any kind of formal date and it could just be a hang out or coffee. I never had trouble asking out a girl, but the majority of the girls I've asked out, especially the ones during college were people who I have never met before or I have just met recently. I have known his sister well over a decade and it feels like a mental block that I known her for so long, yet I don't actually know her too well, but I want to get to know her but I feel a bit intimidated. It's a bit convoluted.
spiderowl Posted November 11, 2016 Posted November 11, 2016 It actually sounds quite sweet. Good luck!
Author jayaway Posted November 11, 2016 Author Posted November 11, 2016 Haha thanks for the encouragement guys. I think I'm just psyching myself out. This would be the first girl I'm actively pursuing after my long term relationship ended about 4 months back. Honestly it's been awhile since I've been on dates. Any suggestions on good conversation starters? I don't have her number, but we are facebook friends. Like I said earlier, it just feels so weird that I have known her for so long but actually don't really know her well other than what she's currently studying and work.
spiderowl Posted November 11, 2016 Posted November 11, 2016 What does she appear to enjoy doing? Ask her about that. Has she got any pets? Ask her about them, how she acquired them maybe. Ask her what music she likes, what her favourite places are. I am thinking of the 'happy' subjects that my colleagues tend to talk about. 1
phineas Posted November 12, 2016 Posted November 12, 2016 Haha thanks for the encouragement guys. I think I'm just psyching myself out. This would be the first girl I'm actively pursuing after my long term relationship ended about 4 months back. Honestly it's been awhile since I've been on dates. Any suggestions on good conversation starters? I don't have her number, but we are facebook friends. Like I said earlier, it just feels so weird that I have known her for so long but actually don't really know her well other than what she's currently studying and work. FYI your best friend knows if you will be good for his sister or not. FYI if you end up dating and hurt her, he will beat your ass. IF he can't beat your ass he probably has an army of her orbiters he can call on to blanket party you. FYI - ask his permission to ask her out. But only if she has shown even a smidgen of interest in you at all. If she likes you she may not show it because you are her brothers friend. However, I do know guys who have slept with all of their sisters friends which is way different but i'm drinking tonight so whatever.
Author jayaway Posted November 15, 2016 Author Posted November 15, 2016 FYI your best friend knows if you will be good for his sister or not. FYI if you end up dating and hurt her, he will beat your ass. IF he can't beat your ass he probably has an army of her orbiters he can call on to blanket party you. FYI - ask his permission to ask her out. But only if she has shown even a smidgen of interest in you at all. If she likes you she may not show it because you are her brothers friend. However, I do know guys who have slept with all of their sisters friends which is way different but i'm drinking tonight so whatever. Haha definitely if I do end up dating her I'll try my best to make it work. I valued our friendship greatly and would want the best outcome for all of us. I'm actually twice the size of my friend so I should be able to take care of myself if anything ever escalates, but honest to god I would never do anything to deliberately hurt his sister's feelings. It's a bit difficult to judge if she has any interest. Mostly because she doesn't really know me or I know her too well. As of now, she probably sees me as someone who went to her high school and is her brother's best friend and likewise, I see her as a girl that I've known for a long time who I'm currently attracted to and happens to be my best friend's sister.
JoeSmith357-1 Posted November 15, 2016 Posted November 15, 2016 These things usually don't end well for anyone involved, so I have to ask you how good of a friend is this? 1
JoeSmith357-1 Posted November 15, 2016 Posted November 15, 2016 I can tell you that I have seen BOTH sides of this. I know someone who did the exact thing you are contemplating, and he lost his best friend, and after getting the girl in the sack a few times, it was clear they didn't mesh, so that was for naught And I had a (former) good friend of mine bang my sister, who is 11 years younger than us, just out of an LTR, took advantage of her on the rebound. This sort of went on covertly for a while, then I found out after they had stopped, and about beat his ass. This is at age 38 too. It just is not worth it for a piece of ass
Author jayaway Posted November 15, 2016 Author Posted November 15, 2016 Yeah definitely we are really close friends which is why it's a slippery slope. I do however don't want to get with her for a "piece of ass". I wan to see if I can develop something more with her.
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