You've been best friends since school and you together collected Star Wars figures, played games and discussed girls. And you've never had any interest in your friend's little sister, but once he takes her to the bar and you feel that you're falling for her. Now she's not a small child any more, but a beautiful woman and you want to ask your friends' sister on a date.
Affection causes people many problems. We want to have the object of attraction near us, but sometimes it seems to be out of reach, like with your friend's sister. Now you can't come up and use cheesy pick-up lines on her, because there are too many people and relations involved. So before you make any steps towards asking your friend's sister out, you need to decide, what kind of relationship you want.
Hurting your friend's sister will put your friendship at stake, that's why if your intentions are only to bed her, you'd better stay away from this family. In case you can't commit and don't see any long-lasting relations with her, it's also better not to take any actions. The problem is that if you will break up and your friend's sister will be hurt, you never know what consequences you might have.
Talk to your friend about your feelings. You don't want to date his sister behind his back, right? Although your friend has no right to decide whom his sister can or can't date, he might feel like he's in charge. By the way, your friend may be totally against your relationship, because he knows too much about your life.
There's no difference between asking your friend's sister and any girl you like on a date. You have to be a gentleman. Bringing flowers and a box of chocolates is really nice, but it sounds that you're desperate. Instead of that be funny and respectful. Stay confident and calm. Don't be a jerk and don't treat her badly.
You will definitely want to know her better, and you will have many chances for that. At first you might want to arrange a double date with your friend, his girlfriend, his sister and you. There won't be much pressure on this date, but there will be some embarrassing stories and good-natured ribbing.
When you're ready to spend one-on-one time together, there's nothing wrong with it. Just ask her on a date without her brother and his girlfriend. Keeping your relationship separate from friendship is very important. No matter how much you like her brother, don't make it threesome. You friend won't be happy to be around, when you're flirting with his sister, as well as she won't like being with you, when you get drunk and watch basketball with her brother.
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