“A quick check-in can make all the difference in a sexual experience,” says certified sex therapist Kristen Lilla, LCSW, CST-S, CSE-S. She recommends asking questions like Are you OK? Does this feel good? Can I keep going? Want me to stop? “Make sure everyone has consented and feels they have control. Friendships are likely to end if someone feels coerced,” she adds, noting that limiting alcohol is also key in terms of consent. Sexologist and certified sex coach Gigi Engle never recommends threesomes with friends: “I don’t recommend to clients or readers to ever have a threesome with a friend for the exact reason that it can get weird and has the potential to compromise a friendship. I don’t think it’s ever worth the risk when there are so many apps and resources available to find a willing third (or to be one) for a threesome.” If you’re looking to hook up with a friend and their partner, be careful how you approach the situation: “I find couples prefer a stranger because there are fewer emotional consequences. People often want the experience but don’t want the drama or baggage that would come with engaging with a friend,” says Lilla. Prepare for the possibility that they’re not interested in involving you in their sex life. If you’re drawn to the possibility of trying a threesome with a friend, O’Reilly’s ultimate advice is to explore this desire gradually and proceed slowly. That way, you’ll be mentally and emotionally prepared for whatever happens before, during, and after the experience. Mandriota has traveled to a clothing-optional resort in Jamaica, attended sex camp, visited cannabis cafes, tried a liquid vibrator, and spilled her personal dating experiences (read: struggles) on the internet, all in the name of journalism. When she’s not writing, she devotes her time to her passion project Highly Untamed, scoping out the best taco spots, training Brazilian jiu-jitsu, and adventuring around seeking inspiration for new stories. Follow Mandriota on Instagram and Twitter or visit her website to read more.