Cloverwitch

That's a very precarious situation.

It entirely depends on the person, your relationship, etc. Trying to cross that boundary from friends to partners can ruin friendships if it's not reciprocated. I've had a few friends try that, since my break up, and it honestly really upsets me. I'm just me though. I'm a pretty up front person so I would just ask them on a date, and be clear that I mean it in a romantic sense. If they turn you down, though, you better be okay with just being friends or be honest that you can't not see them romantically and stop hanging out. Also be ready to lose them as a friend if they react badly.

I'm not a social person, and I have very few people I consider close friends. Literally just Jordiboii, Ghoul, and Dany at this point. Those three know that I'm not interested in dating any of them so if they tried I'd be pretty upset. Everyone is different though and maybe your close friend feels the same as you, if you're not ok with jumping straight in, maybe try testing the waters with asking them questions about whether they are looking to date, what their type is, maybe ask them to define your friendship or ask them what they like about you. If they refer to you as a good friend and/or 'like a brother/sister' please take that as a bloody clear sign they aren't interested.

It's true, I am smol. The boots make me feel powerful though.

Mass hypnosis and REALLY tall boots?