Talking to boys on dating apps is hard

I find it hard to talk to people I dont know, because I dont have a reason to talk to them so I dont say what to say.

So my friend told me to make a joke or something. On this one guys profile it said he likes tuff girls. This is how the conversation went and how I responded to his prompt:

Prompt: I like tuff girls

My Message: Does a black eye make me tuff?

His Message: Maybe. how did you get the black eye?

My Message: These women get rowdy in this prison

His Message: You work in a prison?

My Message: No

His Message: Your in prison?

My Message: No

His Message: Visiting?

My Message: No

His Message: How did you get a black eye?

My Message: I dont have a black eye

See its hard to talk.

No, I think your mistake is bringing up a subject like a black eye and then way down the conversation saying you don't have one. Why not just ask him what he means by a 'tuff girl'? Or what makes a tuff girl? Or why he wants a tuff girl? Or better still what attracts him to the idea of a 'tuff girl'?

That said at least you've started a conversation even if it's a bit awkward. If it gets to a point like the above just ask a question about him or any question as long as not too far off track to keep things going. If you keep things going any initial awkwardness may get forgotten about, or mostly forgot about/little importance.

If you're not a tuff girl as I'm suspecting your not then maybe not go for guys that are after a girl which you are not. Unless he is mistaken in the sort of girl he wants to be with it would kind of be strange for a meek & mild girl to turn up on a date when he was after a tuff girl.