Can I Date My 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. 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. You’re pretty sure you want to get to know her better, but you feel awkward even mentioning it to your friend since you don’t know what his reaction will be. Can you date your best friend’s sister?

What Kind of Guy is Your Best Friend?

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. After all, how would you feel if he wanted to date your sister? Think about that: Even if you don’t have a sister, you can still probably put yourself in his shoes.

You’re likely familiar with your best friend’s good points and his flaws. Do you think he’d be uncomfortable or angry with you if you date his sister? Is he over-protective of his sister? Remember — this is the guy that you’ve been bouncing off dating questions for years, as well as the only other person on Earth who knows anything about your sex life, besides the girls that were involved. 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?

Before you even head down a potentially rocky road, figure out how much you really want to date your friend’s sister. Is it merely a desire to bed her or are you intrigued enough to want a relationship with this woman? If you can see a possible future with her or, at least, some kind of longer-term commitment, then it’s likely worth any possible friction between you and your friend.

Your best way to go about it is to be absolutely upfront with your friend and tell him how you feel. This should occur before you even ask his sister on a date. You’ll take a chance that you caused a lot of ruckus to go down between you and your friend, only to find out that she has zero interest in you at all. But no doubt your friend will remember and respect that you didn’t go behind his back and ask her without him knowing.

He’ll want to feel like he has a say in the matter, even if it’s really something that involves just you and her. 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. After all, by turning you down after years as his best friend, she’s also insulting his taste in friends, and siblings always take things personally. Don’t be surprised if he harbors a far greater grudge against her than you do if this happens.

How to Ask Your Best Friend’s Sister on a Date?

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. So don’t treat her like a little kid. How do you ask any woman on a date? Do the same thing, only do it better. Leave the cheesy pickup lines behind.

We talked about using the direct, honest approach with her brother, and there’s nothing wrong with using it with her too. Frank admiration makes a woman feel good. Tell her how good it is to see her again, after all these years. Tell her how amazing she looks. Let her know that you’re interested in her, if not vocally, at least with your eyes.

If it’s easier, perhaps you can arrange a double date with your best friend, his girlfriend, you, and his sister. This type of date is sure to feature some good-natured brother/sister ribbing and, no doubt, some embarrassing stories swapped between the two. 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. You’ll still get to know her, just without your friend’s antics getting in the way.

If the two of you end up getting serious–for however long it lasts–take pains to make sure your best friend doesn’t feel left out in the cold. Grudges and hard feelings can develop quickly when somebody’s feelings are hurt. Recognize that he’ll feel more connected and quite possibly more personally invested in this relationship than he’s been in any of your previous ones. If she’s worth it, it’s a small price to pay for dating your best friend’s sister!