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First hand experience here, I've been dating my good friends sister for 4.5 years now and we're better friends now than when I started dating her. It can work just fine provided you're not an asshole and treat her with respect (which you should do with anyone, but I digress). It's basically the same as dating anyone else but you obviously don't tell your buddy about your sex life with his sister.
For starters since he seems quite protective of her be sure you want to date her, not just hook up with her, and be sure she's at least friendly with you (and maybe a little flirty) before you do anything else. Second, you don't have to ask his permission to ask her out, you're adults after all, but you should give him a heads up before you ask her out. Let him know you're not just trying to hook up with her and such. If you end up dating how you treat her will have an impact on your relationship, it sounds like you're a decent guy with your shit together so you should be fine.
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1991 Toyota Celica GTFour RC // 2007 Toyota Rav4 V6 // 2000 Jeep Grand Cherokee
1992 Toyota Celica GT-S ["sold"] \\ 2007 Jeep Grand Cherokee CRD [sold] \\ 2000 Jeep Cherokee [sold] \\ 1997 Honda Prelude [sold] \\ 1992 Jeep YJ [sold/crashed] \\ 1987 Mazda RX-7 [sold] \\ 1987 Toyota Celica GT-S [crushed]
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Originally Posted by maksimizer
half those dudes are hotter than ,my GF.
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Originally Posted by RevYouUp
reading this thread is like waiting for goku to charge up a spirit bomb in dragon ball z
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Originally Posted by Good_KarMa
OH thank god. I thought u had sex with my wife. :cry:
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