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CHECK FOR MUTUAL INTEREST. Make sure you’re both on the same page about exploring an intimate relationship, says Fariello, who’s also the founder and director of the Philadelphia Institute

for Individual, Relational & Sex Therapy, a therapy practice specializing in sexual health. Possible talking points: “I’ve been wondering: Do you ever think about how our relationship

could evolve beyond just friendship?” and “Do you think it’s possible for two friends to become more physically intimate with each other, or do you see that as boundary?” BE TRANSPARENT

ABOUT YOUR INTENTIONS. If you just want to have sex, fine, but if you want a relationship as well, you need to disclose it at the outset, says certified sex therapist Amanda Pasciucco,

adding that it’s important to maintain a level of trust between the two of you. GIVE YOUR FRIEND ROOM TO RESPOND. “Let your friend share his thoughts, feelings and any concerns,” Fariello

says. “Conversations about intimacy should involve both parties equally, and it’s important to listen to his side.” What if he’s not into it? Acknowledge and respect his boundaries if your

friend is not open to a sexual relationship, Fariello says. If your friend _is_ up for it, do some emotional prep work. FIRST OFF, A PEP TALK. “Start by reminding yourself that you really

can do this,” says certified sexuality educator Jane Fleishman. Getting close to someone sexually can be scary or exciting or awkward — or all of those things, Fleishman says. Take your

emotional temperature and be kind to yourself. If you notice that you’re feeling tender or vulnerable, that’s OK. “It’s a good thing,” she notes. “Stay curious about how you’re feeling.”

And, if it’s comfortable for you, Fleishman suggests talking about your feelings with a trusted friend.