How can I tell if it's really flirting or a joke?

There's this guy that I've been going to school with for 9 years so we're really close friends. Recently though we started talking more and I really am starting to like him as more than friends. So I've been super flirty and he has been flirty too. Only thing is I can't tell if he is joking around. A couple years ago we did jokingly flirt over text but we both knew it was a joke. I don't wanna straight up ask him cuz I don't wanna ruin our friendship by making it awkward. So what are other things I can do/ look out for to see if it's real flirting or a joke?
Asked Aug 03, 2015
Ask him out for an event, (just the two of you), dress differently like on a date, hold his arm, the gf stuff and then I would sense if he's uncomfortable and if so you have your answer if not ask him if he'd like to go out with you as more than friends.
Answered Dec 12, 2015
I don't understand what you mean by "if he's flirting or joking?" because flirting actually means to toy or play with another's affections, to behave or act lovingly without serious intentions, basically flirting is to make the other person feel good about themselves. and it just seems that joking could easily fit into that same category also.

I guess the only way to find out if he could be at all be serious is to step out of your flirty, joking comfort zone and start talking seriously together.
Answered Dec 15, 2015

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