alex1960 Posted May 28, 2011 Posted May 28, 2011 One of my very best buddies has a beautiful and smart sister who I've been interested in for a while now. I once approached him about it and he told me to forget about it... Fast forward to today... His sister will soon travel to visit a friend and it happens that I'll be in the same city. He suggested we could potentially travel together and maybe have dinner over there. Do you think I was basically given the green light to court her?
sanskrit Posted May 28, 2011 Posted May 28, 2011 Not really, more like he expects you to keep the wolves off her, but this could be the entry to a courtship in itself. Seeing how she acts traveling will be a great opportunity to see the real her free of social and community restraints, so good luck.
Sivok Posted May 28, 2011 Posted May 28, 2011 No. Guys are blunt, not subtle like women. He's saying you can hang out with his sister, not necessarily giving you the greenlight to penetrate her. If you two meet and hit it off, he really doesn't have much of a say in the matter. Just be very aware that it may permanently damage your friendship
vsmini Posted May 28, 2011 Posted May 28, 2011 Find a nice way to basically tell him he doesn't own the rights to his sister's business and what she does. Point out to him (if this is true, I assume it would be) that he's obviously friends with you because he thinks you're a good friend, and hopefully he thinks you're a good guy - so he should be happy his sister is with a guy he can trust....that should mean something, right? But also keep in mind what might happen down the road - if you get serious with her and it doesn't work out....the breakup might be tougher.
Author alex1960 Posted May 28, 2011 Author Posted May 28, 2011 Thanks guys. I would assume based on my known interest that he wouldn't put her in this situation if he weren't prepared for something to possibly happen. She's in her late thirties and a grown up. I know she is available and since I'm his best buddy, I'm sure he would tell her nice things about me, and I've mildly flirted with her on messenger. Am I pushing it? I really would love to give it a try. We are both at a point in our lives that we would be a good fit.
sanskrit Posted May 28, 2011 Posted May 28, 2011 She's in her late thirties and a grown up. Would have been helpful to have this tidbit in the OP, was envisioning a naive college student traveling to the big city, tell her bro to grow up and that his sister is completely capable of taking care of herself at her age. One other angle, though, is that your friend could be protecting -you- if he knows of any bad habits of hers. He probably wouldn't air family laundry, but try to steer you clear. Just something to keep in mind.
Author alex1960 Posted May 29, 2011 Author Posted May 29, 2011 The good news is that my friend is really encouraging me to try dating his sister. Even if it doesn't end up be a LTR, he's fine with it. The not so good news is that I don't really know how interested she really is. I hope he's not lining me up to get shot down!
Mutant Debutante Posted May 29, 2011 Posted May 29, 2011 Are you sure he's had a change of heart and is greenlighting you? It could be weird mixing family and friends like that, and I've read you before. No offense but I wouldn't want you dating my sister either no matter how old she was.
Author alex1960 Posted May 29, 2011 Author Posted May 29, 2011 Are you sure he's had a change of heart and is greenlighting you? It could be weird mixing family and friends like that, and I've read you before. No offense but I wouldn't want you dating my sister either no matter how old she was. No offense taken. My buddy is well aware of my flaws (and qualities). He very clearly told me to go ahead.
iJester Posted May 29, 2011 Posted May 29, 2011 Don't go into it with any expectations. Just go with her and have a good time, and if anything more is going to happen, it will probably be apparent very soon.
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