big woman in a little world

I think my mindset going in is mostly “You should know that I won’t know what I’m doing yet, but I really want to find out”

When’s the right time to tell a man you’re interested in sleeping with that you’ve never had sex? For context, i’m in my mid 20s. For some men that’s a dealbreaker and for others they’re weirdly obsessed with it.

I guess the question in general is when is the right time to tell someone sensitive information that could affect whether or not they would want to sleep with you

There’s also not some specific reason why I’ve never had sex with anyone it just hasn’t happened yet

When you feel safe enough to do so. I would also say it's your business and you don't have to tell someone, I suppose, unless you really sense it would be a deal breaker for them. Why someone might feel off about it is assuming pressure to make it "special" - especially if you're not really together but seeing each other casually. So, I'd say you can clear the air from that angle: I haven't had sex before, I'd like to have sex with you, but I know we're casual, it doesn't have to be romantic to be special to me. I just like you.

I'd say it's probably a good idea to sus out his feeling about it before hand if only because it's a man. Men, as we know, can be freaks. If he starts projecting some sort of virgin fantasy on you, that's not going to be a good time, and maybe even unsafe. But if he's just in general nervous about making it special for you, you can try to assuage those fears by being frank about your expectations.