I’m seeing a bisexual man who hasn’t dated men before

I’m a 25-year-old gay man and have only really been dating for about 2 years. I recently met a 22-year-old on a dating app, and we’ve had five dates. I really like him, but I’m worried about how things are progressing.

He is bisexual, and told me that he hasn’t dated men before. He wants to take it slow, but we’ve only had a few brief goodnight kisses after dates, nothing more. I can feel myself getting emotionally invested in him, and I think physical chemistry is important in a relationship, so I would like to take things in that direction to see what it’s like.

I’m worried about spending more time with him only to discover that he actually doesn’t want to date or have sex with men. I have some anxiety anyway so I’m not sure if I’m overthinking this, and I don’t want to come across as needy, but I don’t want to get attached if he isn’t interested.

Let me say this first: five dates do not entitle you to sex. In fact, no number of dates entitles anyone to sex.

‘I’ve never dated anyone or had sex. I feel like a failure’

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However, five dates do entitle you to initiate a conversation around expectations, and I’d encourage you to do this. You met on a dating site, so the intention of dating has already been established since the get-go – the conversation now must be how you both see your connection progressing.

These questions aren’t only natural, but expected. After five dates, you’ve likely swapped insights into your favourite pop culture phenomena, shared a bit about your friends and family, and begun to notice and appreciate the small things that make someone unique – their sense of humour, their quirks, their communication style. Seeing as you’re both still going on dates with each other, there is obviously a sense of enthusiasm about each other.

I understand that these conversations can be nerve-inducing. There’s an ironic – and, I believe, stifling – trend in modern dating to go out with someone repeatedly, even have sex with them, but steadfastly refuse to admit that you may actually like them. A disturbingly common view permeating the dating scene is that openly expressing enthusiasm, feelings or attachment is somehow uncool, weak and “needy” state.

This is nonsense; cowardice masquerading as bravado, game-playing masked as nonchalance. Pretending not to care about people we care about doesn’t make dating easier – it negates our ability to express ourselves openly, to seek out what we truly want. And, as you’re experiencing, it usually causes anxiety.

So start talking. Tell him that you’ve really enjoyed your time together, and that you’d like to check in with them about how he is feeling and what his expectations are around the romantic and sexual aspects of your connection.

He may say that doesn't want to have sex unless he's in a committed relationship

Tell him what you have told me – that you value physical intimacy and see it as an important part of exploring your connection with someone. Does he feel the same way? Does he see that as a potential progression for you two, together?

You might feel like these are inappropriate questions to ask – they’re not. In fact, they’re vital. There’s a huge difference between pressuring someone into sex and opening up a dialogue around your expectations so that you both feel comfortable and understood. You’re doing the latter. Make sure your tone and the setting reflect this – there’s a huge difference between saying over dinner “So, I like you. Do you mind if we have a chat about how feel this has been going?”, and cornering them near your bedroom with a “So, we doing this?”

He may say that doesn’t want to have sex unless he’s in a committed relationship. He may say that he wants to get to know you better. He may say he doesn’t see you two becoming sexual.

You will, of course, respect his decision, whatever it is – even if it isn’t the answer you were hoping for. But you will have clarity, and you’ll be able to decide what is best for you – to continue dating him, to emotionally divest slightly, or to find someone who is more on your wavelength. Your feelings are important, and you get to protect yourself from anxiety and the potential hurt of investing in someone only to discover that you don’t share the same vision.

I will say, please be sensitive to his situation. If he hasn’t dated or had sex with a man before, it is understandable that he is moving slowly and carefully through this new part of his life. It might be worth asking him about his support system and how he’s feeling. If he is bisexual but has only dated women, it could be that the people in his life don’t know that he is attracted to men. Getting emotionally invested in you could mark a huge shift for him, and mean that he might have to come out to more people. It’s an important time in his life that may be influencing his thought process, so do be mindful.

But also be brave. You like someone. Let them know. We could all do with feeling a little more cared for.