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It is really okay to go out with your friend’s sister as long as you handle the situation well. Most guys are very possessive about their sisters and if you are the type that likes to flirt around and if this friend of yours knows about it then you are a dead duck! You will obviously have to be a little manipulative in order to maintain calm and peace between the friend and the sister.
The first thing that you should know is that, guys no matter how flirtatious they themselves are, would always want their sisters to settle down with guys who have never had a girl in their lives. As much impractical it may sound, it is the truth. Therefore, your chances initially will be slim as I am sure you don’t belong to that group. Don’t tell your friend that you have a crush on his sister. If you are flirting around with other girls, in the mean time, don’t let him know that. Start doing something nice for the friend. Remember that the friend knows you well so please don’t take a three sixty degree turn and become overtly nice. Change gradually and stop talking about girls as much as possible. Tell your friend that your interest has shifted from girls to something else, something that is much more serious and mature.
Make yourself a little boring and uninteresting but not stupid. Hang out with your friend as much as possible and do something for him that will make him indebted to you. Start meeting her sister in front of him, never allowing him the feeling that you like her. Treat her casually but in a friendly way. Do not flirt with her when her brother is not around. She should be able to trust you. Once a foundation has been laid and you guys have met several times, you can ask her out but off course with your friend’s permission. He may or may not grant you permission; this will depend totally on how you present it. Tell him that you are just taking her out for lunch. This is a very safe option, as your friend will know that you can’t get physical with the girl in broad daylight at a restaurant. Convince the girl to go out with you as well.
Once you manage to take her out for lunch, keep repeating the process till the brother relaxes. By this time, I am assuming that you would have charmed the girl enough, to actually want to go out with you. Next, move on to the movies, this is a slightly more dangerous situation for the brother as once the lights go out anything can happen between the two of you. Once you have repeated this process take her out for dinner. But always remember to drop her home after that.
It might sound tedious but this is the best way of handling a brother. By the end of, say, two months you will not only have a girl to love and sleep with but also a brother and a friend.
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