Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I have been gay in theory but not in practice for my entire college experience so far. My best friend (also a guy) of a few years and I have always had kind of a flirty friendship.

Last year, he came out to me as bi. I’ve always known I wanted my first time to be with someone special who I really liked, and I think I’d like it to be with him. To be clear, I don’t want to be in a romantic relationship with him; I just want to go from best friends to best friends who also have sex. I have no idea how to approach a conversation about this, though, especially because I’m pretty sure he’s only ever dated and slept with women. I want to do this with tact because our friendship is important, but I also think there’s a pretty good chance he would be interested. Obviously, I can’t just say, “Hey man, do you wanna like take my virginity and then go get some pizza?” Any thoughts on how I should approach this?

—Best F*cking Friends

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Rich Juzwiak: The thing that gives me pause, and I wonder how you feel about this, Jessica, is the sentiment, “I’ve always known I wanted my first time to be with someone special who I really liked, and I think I’d like it to be with him.” That is cute and sweet, but it immediately puts pressure on the situation that I think could be a turnoff or even friendship-altering. There’s a kind of weight there all of a sudden that I would advise against. Make it chill. If that is the underlying impetus for this, I would say keep that quiet.

Jessica Stoya: There’s so much going on here. First of all, especially when we’re talking about two dudes, you usually can just say, “Hey man, do you want to take my virginity and then go get some pizza?”

Rich: That’s another thing.

Jessica: Furthermore, as a woman having sex with dudes, not the virginity part, but “Hey, do you want to bang and then maybe go eat some food?” goes over pretty well a lot of the time. Why can’t you just say that?

Is there some reason that you can describe and then think through? Or is it this thinking that it’s not how it should be done? And that same pair of questions is worth applying to wanting your first time to be with someone special you really like, but also not wanting to be in a romantic relationship with the person you’ve decided on. So what’s going on there? Because usually the specific phrasing of “first time with someone special” means romance is part of the package.

Is it that you want your first time to be with someone that you respect and feel comfortable around? Great. Maybe don’t use the “someone special” phrasing, because that tends to send people thinking in a certain way. Or is there one of hundreds of different possible contradictions going on that’s leading to this “someone special” idea?

Rich: I fully believe in pursuing the happiness you envision in your life, but there’s already a kind of micromanaging approach here that just does not really bode well for satisfaction. The expectations of, I want it to be like this, but not like this, and I want it to hit this precise mark where he’s special but not romantic, and now we’re friends who have sex. This stuff is kind of out of your control. Part of the experience of interacting with people on this level is that you surrender a bit because you have a whole other person involved with their needs, wants, and volitions.

So then what happens when your friend says, “Oh, actually, I do want to have a romantic relationship with you if we’re going to have sex”? Is that a no? I think there needs to be a little bit more of an agnostic mindset going into this if you’re going to propose this, which, by the way, is a dangerous thing to impose on a relationship. Yes, it can go super, super well, and you might end up having a great time with your friend, but it can also torpedo this thing that you have with your best friend just because sex is a real wildcard.

Jessica: I think the main thing that makes sex such a wild card is the ways that it causes so many different feelings. And those feelings might be temporary. Those feelings, if you have self-control, do not need to have anything to do with the actions that you take, but you’re going to feel feelings of some kind. Maybe it’s romance, maybe it’s disgust, but you’re going to be feeling a lot.

This person has never had sex with another man. I’m not sure they’ve had sex with anyone at all. I’m leaning toward not. You don’t know what’s on the other side. You don’t have any experience from which to start speculating and understanding yourself. So it’s really sweet, and it’s understandable. He’s in college. It’s an age where we have a lot of stuff in our brains, but we haven’t gotten to road-test all that much of it. But it’s not very realistic to think that he can even say for himself how he’s going to feel and what he’s going to want after he has sex for the first time.

Rich: That’s right, yes. This is the process of relinquishing some amount of control. It is good to have goals and a vision when you go into something, as long as you realize that that is all subject to change as soon as it starts happening. I would, again, just take it out of the realm of “this is so meaningful to me.” If you really want to approach this as a very casual kind of thing where you’re not declaring love to this person, you’re just saying, “This is sexual,” and just make it a completely practical proposition like, “I’m horny. Do you want to get off?”

Jessica Stoya
I Was Fine to Give the Guy I Was Hooking Up With an Assist the First Few Times. But Three Strikes and You’re Out.
Read More

Jessica: When I had sex for the first time, I went to the mall, I picked someone who looked fairly clean and had a driver’s license, and then I asked them if they would alleviate me of my status as having not had sex. At about the same age, one of my peers pushed for, and got, the hotel room with the boyfriend. I think there were literal rose petals scattered everywhere. She got that experience, and she got herpes.

Rich: Wow.

Jessica: So, just to put forth, for me, it was fine. It was nothing spectacular. I don’t know that it’s all that common for people with vaginas to have a truly spectacular time during their first experience of penetration.

Rich: You don’t often hear that story. I feel like the best thing for your friendship is not to pursue this. Just being totally safe. But if you’re going to, just keep it very much in the realm of the practical. And if you need to talk about these feelings, wait until you’re already in the sexual relationship to reflect on them. Don’t lead with them, because that could just undo your cause immediately.

I Was Fine to Give the Guy I Was Hooking Up With an Assist the First Few Times. But Three Strikes and You’re Out.

My Wife Has a Disturbing New “Policy” About the Kids Next Door. I Want No Part of It.

Jessica: I think also something that will serve the writer well, in general in life, is learning to consider: What does this phrase or word actually mean to me? So, when you say you want your first time with someone special, what does special mean to you? And that can, in this situation, probably help them wrap their head around whether it’s actually worth it for them to risk blowing up the friendship. Then, as you’re moving through life, and you find yourself saying a cliché phrase, take a second to go, “What do I actually mean here?” It helps.

Rich: Don’t take it for granted. Also, another kind of path, if he has the patience, and since the relationship is already flirty, would be to just keep pushing it in that direction and see where it goes. If you’re already on that beat, just keep it going. It might feel more organic that way.

Jessica: Also, how did the guy come out as bi? Because some people, it’s a big part of their identity that they want to share with lots of folks, like, “Hi, my name’s George. I’m studying biology, and I am bisexual.” But there are plenty of other folks who aren’t as obvious because they’re not saying it out loud. They’re going to tell you if they’re hoping that that puts it in your head that maybe the two of you could have sex. So was this a matter-of-fact aspect of who they are? Or was the information delivered in a flirtatious manner? If it’s the latter, you can really probably just say, “Do you want to have sex?” And he’s probably been waiting for you to do that.

More Advice From Slate

My wife and I are a young-at-heart couple in our mid-50s but presenting measurably younger. I, for example, have managed to keep all my own teeth, my hair in nearly the same color as my youth, and I can see all my toes when I stand up. By the standards of straight middle-aged men in the U.S., I’m a 10! Our sex life as a couple can be characterized in a word as “ecstatic.” Our problem/query: We don’t find ourselves invited to any group sex encounters?

Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays.