Pillowtalk,

I’m having sex with my best friend. I’m panicking because we’re both new to boundaries and he wants to keep things platonic whereas I’m hopeful it’ll lead up to something. Help! Is this weird? Is it right? Are we just ruining our friendship for nothing!!!

This question seems urgent, so I’m answering it ASAP! My best advice to you, my friend, is to talk this out with your best friend using a few key questions about physical boundaries, emotional boundaries, and your attitudes towards sex and friendship.

However, I do have to warn you that expectations are the worst thing to bring to a sexual encounter. If you’ve had a conversation that has confirmed that your friend wants to keep this platonic and doesn’t want anything romantic or long term out of this, that should be enough for you to know that he will probably stand by that. If he believes you’re totally on board with the platonic thing when you’re actually hoping for a relationship, that’s a huge opportunity for falling out, distrust, and miscommunication. You have every right to hope! But you cannot let that dictate your expectations, or you will be setting him and yourself up for failure.

Does he know? You also should be communicating these hopes to your best friend, which I know is a daunting thing to say. Platonic/romantic intentions change the context of the sex, and therefore might change what someone is comfortable consenting to. If you want a romantic relationship, that might mean he would rather not have sex at this point. If he doesn’t care and is fine with continuing having sex, understand that means he has no responsibility for those feelings and it is your job to decide if it’s going to harm you or complicate your feelings toward him to be in this arrangement.

Sexual experiences between friends can be some of the most comfortable, rewarding forms of intimacy! If you talk to each other and you’re sure you want to continue having sex, all the more power to you! That’s an incredible thing to get to experience; convenient, friendly, fun, and caring. I’m fully of the belief that sex doesn’t have to be romantic to be fulfulling.

You want to know if you’re going to ruin your friendship, and I hope these questions can help you determine that. First, you’re going to want to be alone. Tell him you want to talk about having sex and boundaries. Ask if it’s okay if you go through a list of questions together to help clarify expectations. Then, sit down together and talk:

-What kinds of activities are you okay with/interested in? What’s on the “no” list? Penetrative sex? Oral? Anal? Kissing? Sexting? Dirty talk? (You should also talk about preferred names to use for each other and your body parts, as well as specific boundaries/needs with your body, like if you hate having your feet touched or you can’t kneel.)

-Are you going to be sexually monogamous with each other? If not, do they need to know about your other partners?

-Is it okay if people know/find out? To what extent?

-What kinds of protection will you be using and who’s bringing it? Do you plan to get tested for STIs and how often?

-Is kissing, cuddling, touching, etc. okay to do even after sex has ended? To what extent? 

-If someone catches feelings, what should you do? Would you prefer they tell you or not? Should the sexual relationship end? (The answer to this question should lead you towards talking about your hopes.)

This should give you a starting point for talking about boundaries, and a good place to build your skills in creating and communicating boundaries for future sexual relationships, too. Too often, almost none of these questions are talked about. You have the opportunity to make purposeful boundary setting and communication a staple in your relationships! By asking this question and putting yourself in this situation, you’ve given yourself an incredible chance to get really good at boundaries. 

But again, be careful. You’re playing with fire, and I know I’m not alone when I say that unrequited feelings in a sexual relationship between friends is a disaster waiting to happen. Don’t risk an incredible friendship for sex unless 1) it’s really good sex AND 2) you’re confident in communicating and enforcing boundaries with that friend. I wish you the best in attaining both. Don’t be a stranger, and remember to use lube!