My best friend is in love with me and I don’t know what to do

Dear Roe,

Four years ago, in my first year of university, I met my now best friend. We went on a few dates before sleeping together, where I told him halfway through the sex that we should just be friends. Needless to say, it was really awkward; I felt really bad for blurting it out and he was pretty offended and embarrassed. We met up and talked it through and decided to be friends. We’ve been best friends ever since. We have both dated other people but neither of us has been in a long-term relationship. We’re super close and see each other most days, and even went on holiday together. People always mistake us for a couple, and our friends and family have commented on the unusual nature of our boy/girl friendship (most don’t know we slept together once and it didn’t work out). A few months ago, he started joking about us sleeping together but it was pretty light-hearted and fitting with our humour as friends – until he proposed seriously that we should sleep together, and said he’d been thinking about it for a while. To make matters more complicated, he has slept with most of my close friends and was sexting one of them literally while we had a conversation about whether we should sleep together or not; when I found out I was pretty upset. We hashed it out and I made it clear I didn’t want to sleep with him, so we decided to put it behind us – he said he just was feeling confused and a bit lonely. It was normal for a bit, until the other day when he said he wants to be in a relationship. It’s put me in a really difficult position. I don’t want to lose our friendship, but I don’t know if it can continue if he has such strong feelings. But I find it disrespectful that he has suggested it again after I said no. My gut feeling is that I don’t want to be in a relationship with him, and the thought of sleeping with him does not excite me. How do we move on? Can our friendship last?

I say this with love: some of the answer to this is simply that you both like a bit of drama. I do genuinely mean that with love – you’re young, it’s the time to indulge in drama if you are so inclined. Lots of us have indulged in drama (myself included) and lots of people who are older than you with more serious attachments and responsibilities and loyalties still seek out drama at the expense of other people, and that’s where drama becomes gross and immature and unethical. For now, you’re both young and single and the only people you are going to hurt are yourselves and each other – not ideal, but as drama goes, that’s often the best-case scenario.

I think you both like a bit of drama because you indulge it – the drama that other people create around your relationship, and the drama you both create yourselves. You like that other people think you’re a couple, you like that people think your friendship is so “unusual”, you like making jokes about sleeping together but making it clear that you don’t want to sleep together, but also getting upset when the other sexts someone else.

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To make a sweeping generalisation, people who like drama are often bad with boundaries, a bit scared of authentic emotion and connection, and value love incredibly highly – so highly that they fear losing themselves to it completely, so they keep it at a distance. That could look like, for example, becoming incredibly close with a best friend to the point that neither of you need to date anyone seriously, because you get a lot of your emotional needs and desire for validation met, without having to do the work of being someone’s partner.

It could look like claiming you have no desire to be in a relationship with someone but joking about sleeping together and becoming jealous and punishing them for sexting someone else because you rely on them somewhat to feel like you are desirable, without having to deal with the vulnerability of desiring them back. And it could look like your best friend declaring that they have feelings for you and instead of examining your feelings, focusing on how “disrespectful” it was for him to tell you that he has feelings for you, when what it sounds like was him offering sex because that felt emotionally safer, before blurting out the truth and giving you the full context of his feelings so that you could make an informed decision.

And as your friendship evolves, how are you going to evolve with it? What do you want to prioritise, keep, and make room for?

This may sound dismissive, but drama like this actually serves some really important purposes. It lets us explore what we want and what we’re afraid of with someone who cares about us. I think you have both been using each other as an emotional safety net, exploring the contours of each of your limits around emotional intimacy, around sex and friendship, around your desire for or ability to have a romantic relationship, and that’s fine and healthy – and that time is coming to an end, which is also fine and healthy.

Relationships evolve as people’s needs change, and that’s what’s happening. The charged dynamic-meets-emotional-safety-net of your friendship once served you and your friend – and it’s no longer serving him. He wants more. He wants a relationship, love, he wants to be vulnerable and honest about his feelings and to be met with vulnerability in return. He wants more, he’s asking you to be part of that, and if you don’t want to, that’s completely fine – but I do think the nature of your friendship is going to change so that he can find that more with someone else. You might find it with someone else too, if you want. But there has to be room for the more, and right now, you’re taking up too much unboundaried space in each other’s lives for that to happen.

[ I love my girlfriend’s weight gain but she doesn’t – how can I boost her confidence? ]

Your relationship is about to change, and only you two can decide how. If you want to keep this person in your life, you’re going to need to do what you two have historically been bad at: having open, honest and vulnerable communication, and setting some boundaries. If you don’t want to be with him romantically, what does he need to get over you and move on? If he starts dating someone else, how are you going to cope with the decreased attention? What changes need to happen for your friendship to persevere – no more “jokes” about sleeping together, a little more independence, more honest and direct communication instead of subtext and innuendo and possessiveness?

[ My fiance has a history of cheating – can I trust him? ]

And as your friendship evolves, how are you going to evolve with it? What do you want to prioritise, keep, and make room for? Think about what you want – from him, from this friendship, from love, from sex, and start seeking it out. Drama is the rehearsal. Are you ready for the real thing?