5 Crucial Dos and Don’ts for Dating Your Friend

Mindy Kaling and Chris Messina
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They say the best relationships start off as friendships, but what they don’t mention is how tricky it can be to go from friend zone to couple status. (Just watch “Pretty Woman” if you need a refresh on what a minefield that transition can be.) If you’re interested in dating your friend, chances are you probably value that relationship enough to be concerned about losing it if things don’t work out romantically. That’s why it’s smart to be a little strategic about your next move.

“Sometimes friendships that have a certain chemistry will slide right into friends-with-benefits, which sometimes doesn’t work out, if you’re looking for a relationship,” says loveologist and sex educator Wendy Strgar, author of Love that Works: A Guide to Enduring Intimacy. “There are risks when you become romantically involved with a friend, but the risks can be worth it.” 

Here are some important dos and don’ts you’d be wise to keep in mind if you’re considering taking a friendship to the next level. 

Do Listen to Your Gut.

As we’ve discussed before, the virtues of tapping into and heeding the wisdom of your intuition should never be underestimated. And that’s just as relevant here: “Tune into your own sensitivity to your chemistry with others,” says Strgar. “Pay attention and trust your feelings—if you’re sensing an electric charge during everyday interactions with this friend, there’s a good chance you’re not the only one feeling it.” If the chemistry’s clear to you, even if it’s subtle, you’re likely to get a positive response when you approach your friend to see if he or she is feeling it, too.

Don’t Rush Things.

That whole sliding into friends-with-benefits before you’ve really thought it through or talked it out: It’s a bad idea if you’re actually interested in exploring a relationship with your friend. “It can sometimes preclude you from getting what you want,” says Strgar. “Adding sex before establishing that emotional connection makes it hard to go back, because you’ve exposed a degree of vulnerability that can’t be reversed, and often becomes a burden. Then people tend to pull back.” Take it slow—what do you have to lose?

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Do Know What You Want.

Reflect carefully on what you’re looking for out of the relationship before diving into one. Are you looking to explore the possibilities without any pressure? Are you looking for something serious and committed? Do you just want to be friends with benefits? Be clear on your vision before taking the next step with a friend. “When you come into a conversation knowing what you want, it doesn’t matter how the other person reacts, because either way, you’re being honest and true to yourself.” says Strgar. If it works out, great, if it doesn’t, you’ll know you tried and put yourself out there and were authentic. There’s no shame in asking for what you want.

Don’t Ignore His or Her Past.

While you shouldn’t judge your friend for his or her past relationship patterns, or assume that the same will hold true for you when you get together, it’s wise to take an honest look at his or her romantic history. It can hold important clues to the joys and challenges you might experience as a couple. Is he or she a player? A serial monogamist who hates to be alone? A workaholic whose significant other often comes second to a job? “Don’t write anyone off, but also don’t assume you’re going to be the exception if you’ve seen this person treat other partners badly,” says Strgar. “People show you who they are if you let them.” It’s certainly possible that he or she could be a very different partner with you—a close friend—than they were with others, but either way, go into this with both eyes open.

Do Manage Your Expectations.

Something Strgar emphasizes when it comes to all relationships, but especially millennial ones, is not to underestimate the challenges of any relationship, including one that you start with a friend. “I extoll the virtues of friendship before dating because you know each other and you have this sense of safety that allows you to explore the relationship more freely,” she says. “But there are no shortcuts to doing the work of love. No partner, even a close friend, is perfect. It can be arduous and painful to learn the art of being in a healthy relationship, and it takes a lot of practice. Wherever you end up leaving any relationship is exactly where you’ll start in the next one, friend or not.” But, she says, love is worth it—especially the love that’s born of friendship, because you’ll always have the friend dynamic to come back to when you’re fighting or not seeing eye to eye as a couple. Know that it won’t be easy, but going from friends to partners can be one of the most rewarding relationship paths out there.

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