Should You Ask Your Cute Friend Out? Advice From People Who’ve Been There

Relationships are complicated in and of themselves, but when it comes to turning a friendship into a romance, the transition can be especially tricky. With your feelings, and of course, a friendship at stake, dating a friend you’ve known for years can be the best — and most terrifying — thing ever. Needless to say, the deciding factor is whether or not your feelings are returned, and whether you gain a significant other or lose a close confidant.

But while the future may be uncertain, experts say that there is a way to cross the line cautiously so as not to catch your crush off-guard and, at the very least, preserve your friendship if the attraction isn’t mutual.

There’s a famous moment in When Harry Met Sally, when Billy Crystal’s character explains the age old riddle of male and female friendships.

Then, all of a sudden, it happens. Your BFF starts dating that person that you had already expressed interest in. What gives? It can easily leave you feeling hurt, confused, betrayed, and angry all at once — and understandably so. Not only are you dealing with the fact that someone else is dating the person you like, but that someone is your best friend.

Teen Vogue teamed up with licensed counselor Lauren Hasha to bring you some tips for coping with this very scenario. Ahead, find out how you can deal with this type of situation and move forward to mend what might be a broken heart.