Dear How to Do It,

I’ve identified as gay in theory throughout my college years without actually acting on it. My best friend, who is also a guy, and I have had a flirty friendship for quite some time.

Last year, he confided in me that he identifies as bisexual. I’ve always imagined my first sexual experience would be with someone special, ideally him. Just to clarify, I don’t want a romantic relationship; I’d prefer to transition from best friends to friends who sleep together. However, I feel uncertain about how to initiate this conversation, especially since he has predominantly dated and hooked up with women. I want to approach this delicately because our friendship means a lot to me, but I also suspect he might be interested. I can’t just blurt out, “Hey, do you want to take my virginity and then grab some pizza?” Any suggestions on how to bring this up?

— Best F*cking Friends

Responses

Rich Juzwiak: There’s something that concerns me, and I wonder how you feel about it, Jessica. You mentioned wanting your first time to be with someone special. That’s a lovely sentiment, but it might inadvertently pressure the situation, which might alter the friendship. I’d advise against putting that weight on it. Keep it light. If that notion is your primary motive, you might want to keep it under wraps.

Jessica Stoya: When it comes to guys, you can sometimes be direct and say, “Hey, do you want to take my virginity and then get some pizza?”

Rich: That’s a solid point.

Jessica: As a woman, I often find that just saying, “Hey, do you want to hook up and then get some food?” tends to work pretty well. So why complicate it?

Are you feeling hesitant for a particular reason, or is it the thought that it should be done differently? That line of questioning also applies to wanting your first time with someone special but not signaling romance. What’s behind that choice? Usually, saying you want your first time to be with someone special implies romance is also expected.

Are you hoping to be intimate with someone you respect and feel comfortable with? Fantastic. Perhaps avoid using the term “someone special,” as it tends to lead people in a romantic direction. Or maybe there are various contradictions swirling around that add to this notion of “someone special.”

Rich: I believe in seeking the happiness you envision, but your approach seems overly meticulous. Desiring it to unfold in a specific way, with conditions like him being special but not romantic, creates a lot of pressure. It’s important to remember that the dynamics of intimacy involve another person with their own feelings and boundaries.

What happens if your friend expresses a desire for a romantic relationship if sex is on the table? Would that change your stance? There should be an open mindset when approaching this proposition, which can be tricky. Yes, the experience might be gratifying, but it could also risk your current friendship since sex adds unpredictability.

Jessica: A big part of what makes sex such an unknown is the myriad emotions it can evoke. Those feelings could be fleeting. While self-control can play a role, emotions often have a way of surfacing. They could range from romance to regret; you’ll likely feel something.

This friend may have never had sex with another man—and possibly never with anyone at all. You don’t have a clear idea of what emotions might come into play. It’s sweet and understandable; being in college means navigating many thoughts without real-world testing. But it’s unrealistic to think he can accurately gauge how he’ll feel after sleeping with someone for the first time.

Rich: Exactly. This experience means letting go of some control. While having a vision is great, nothing is set in stone once things get rolling. If you hope for a casual encounter, approach it practically, saying something straightforward like, “I’m interested in hooking up; are you in?”

Jessica: My first experience was a bit unconventional. I went to the mall, picked someone who seemed clean, and asked them to help me with my virginity status. Around that time, a peer of mine planned a very romantic encounter with rose petals, and she ended up with an unpleasant surprise. The point being, my own experience was pretty average. Not everyone has a spectacular first sexual experience.

Rich: That’s an eye-opener. I genuinely think it’s best for your friendship to tread carefully on this. If you choose to go for it, please keep things casual. Only dive into emotions after you’ve established a sexual relationship, as leading with those feelings could derail everything.

Jessica: Also, consider how he revealed his bisexuality. For some, it’s a big part of their identity they share freely—like an introduction. Others might hint at it hoping for a sexual connection. Was his coming out casual or flirtatious? If it was the latter, you could probably just go for it with, “Do you want to hook up?” He may have been waiting for that nudge.

Further Insights

Jessica: Think about what “special” really means to you. When you say you want your first time to be with someone special, clarify your interpretation. Understanding this could help you determine if pursuing it is worth the risk of damaging your friendship. Ponder clichés you may use frequently: what do they truly indicate? It may provide you with a clearer perspective.

Rich: Don’t take anything for granted. Alternatively—and since there’s already tension—you might consider continuing to flirt and see where it leads without forcing anything. Just keep the energy alive; it may feel more authentic that way.