my low-self-esteem, socially-inept ass would be in the guy's place, and still think: "wait, could it be that she likes me? wait no, don't jump to conclusions - she said she was talking about her friend, she could just be demonstrating with body language. don't embarrass yourself, take the safe option."
girls, if you like a guy who doesn't have very good social skills - skip the hints, he won't get it. just straight up say it to his face, worst case scenario he'd still be so overjoyed that someone actually likes him that that alone will make him start liking you back if he didn't already.