I know that this is one of those questions that can only be answered by “it depends”, but I’m hoping for really any insight you can offer.

Over the past, idk, just under a year (maybe since I cut my hair short and now look very gay/butch) women have just… approached me, a few times.

I never know how to reply.

For example, a few months ago I went to this party at a bar. I was waiting for a friend in the bathroom so I was sitting alone at a bench by the dance floor vibing. This (very pretty!!) woman came up to me and sat right beside me and talked to me for a few mins before she said she was gonna go get a drink.

Today, a woman (also pretty!) I’ve seen around my school building a few times (but never spoken to) caught up to me as I was walking about a block away from school and asked if I like my brand of shoes and talked to me for about a minute.

I know that it’s ambiguous- in either situation, maybe they wanted to approach me, or maybe they genuinely just wanted a place to sit or had a question.

But both times i have been interested. And both times I have become so shy I just go silent as soon as they stop asking me direct questions and the convo ends. I know I should try to keep it going to feel it out… but I don’t know how! Sometimes questions come to mind but I can’t get the words out. Sometimes nothing comes to mind. Sometimes I get worried I’m annoying them and they just want to go about their day.

Any help or advice would be greatly appreciated.