How To Date Your Friend's Sister or Brother

Updated September 30, 2015.

The only thing more awkward than falling for your best friend's ex- is falling for your best friend's sibling. Add five awkwardness points if that sibling is younger. And add ten if you can remember when that sibling could barely crawl. While this is undoubtedly a touchy situation no matter how you cut it – it's not necessarily a dead end. Heed the following tips to achieve your dreams of finding true love with your bestie's sister or brother -- and keep your bestie from wringing your neck in the process.

Prove Yourself Worthy

If you don't already have a squeaky clean romantic history – start scrubbing now. There's no way your friend will even consider being cool with you dating his or her brother or sister if you have a terrible dating report card, so quit it with the one-night-stands and flaky hook-ups. Start taking dating seriously, or even announce a vow of celibacy – whatever it takes to legitimize you as a viable potential partner in the eyes of your friend.

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Avoid Shallow Flirtation

While you're at it, keep the sexual innuendos and physical flirtations to yourself -- not only in front of your friend (duh), but even when he or she isn't around. You don't want news of potential seduction getting back to your buddy in any way, as it'll overshadow your (hopefully) honest intentions and sabotage your long-term plan. Instead, focus on building a genuine, friendly rapport with your pal's sibling – one that you wouldn't be ashamed to demonstrate in front of Grandma.

Get In Good With The Family

In preparation for your "big move," get on the good side of your friend's family. Not in a shameless "Eddie Haskell" brownnosing way, but genuinely, out of a desire to bond with your future love's parents. (These folks could, after all, be your in-laws someday, right?) Furthermore, having the support of his or her parents when you go public with your new relationship will greatly soften the blow for your friend – and might even bypass any tension altogether.

Move In Slowly

Try to hang in groups, continuing to foster that genuine relationship I mentioned earlier, demonstrating in public to your friend that you legitimately have things in common. Send some tasteful signals that you're interested to see if your friend's brother or sister feels the same way (e.g. compliment him or her; smile a lot). If you feel a spark, move on to the next step…

Give Your Friend The Heads Up

Most importantly, notify your friend of your plan to ask his or her sibling out. This is not so much to ask permission (your friend's sibling is his or her own person, and doesn't belong to your friend, or anyone else, for that matter), but to state your intentions and make it clear that you respect your friend enough to let him or her know before anything happens. Be ready to defend your feelings, and ensure your friend that you genuinely see a potential future here.

Class It Up

Finally, it's time to make your move (remember, ladies can -- and should -- ask guys out, too)! It's important to do so in a respectful manner, demonstrating in person or over the phone that your goals are wholesome. Gentlemen: you can even buy some flowers or write a sweet, funny card to make it especially romantic. As for plans, grabbing drinks is typically a great first date for those of age, but coffee or dinner will provide a more casual opening given the potentially sensitive or awkward circumstances (your friend is likely already worried about what you'll be doing behind closed doors – he or she doesn't want to worry about the effect of alcohol, too). With a little bit of luck and a whole lot of preparation, the three of you will be happily sharing Thanksgiving dinner together a year from now!