I lurk occasionally but I've got a REAL problem here. I wanna keep this as brief as possible but what's the best way to break the kino barrier and kiss someone with some sort of backup in case it all fucks up?

Without typing up too much info: I'm kinda friends w/ this girl and want to see how she reacts to a kiss during a hug but what's my backup if it goes wrong? A sly smile and cockily saying "worth a shot" or will that fuck it up more?