You never really gave her much thought in the years since, but your best friend brought her to the bar last week to hang out and, boy she’s hot!!
Suddenly, you can’t get her out of your mind, and you’re not sure what to do. While it’s not really up to your best friend whether you date his sister or not, if you’re any kind of good friend at all, you’ll take his feelings into account.
A serious kick in the butt is not ruled out I tell you.
Even when complimenting our best friend’s sister, we have to chose our words carefully not to annoy our guy. But I obeyed the rules and never let on to Tom about these thoughts. The most envied dudes are the ones with the most adventurous stories to tell about their conquests and how they go about doing them.So from that sort of mindset, dating our best friend’s sister is just out of the question. We just can’t let our friends know the direction of our thoughts where their sisters are concerned. But like they say, different strokes for different folks. If only I knew Tom was that sort, it would have being a race to the finish line between Skip and I. I wouldn’t allow skip or Tom cast their useless eyes on any of my sisters. Stories like this are the bread and butter of our sit downs.He might simply know too much about you and your predilections to not feel at least a little uneasy at the thought of you dating his sister.How Determined Are You to Date Your Best Friend’s Sister?You have been best friends since the fourth grade, hanging out at the pool together in the summers, riding your bikes in the woods, and collecting Star Wars action figures back when it wasn’t cool.
His sister was never really on your radar, unless she was tattling on you both to his parents or begging you both to play tag with her.Don’t be surprised if he harbors a far greater grudge against her than you do if this happens. The whole reason that you’ve gotten into this awkward predicament is because you’ve only just seen your friend’s sister as a desirable woman and not an annoying little kid. It may be a good way to get to know your friend’s sister a little better without too much pressure.But if you’re ready for some one-on-one time with her, there’s nothing wrong with just straight-out asking her on a date, just the two of you.No guy loves being in the middle of a fight between a bestie and his girlfriend (and in this case, your sister).By dating your best friend’s sister, you’ve done exactly that. You are putting the poor dude in an impossible situation.Plus, in the off-chance that she does shoot you down, it’s much more likely that he’ll take your side and feel just as slighted as you do. If it’s easier, perhaps you can arrange a double date with your best friend, his girlfriend, you, and his sister.