I think the best way to flirt with text messages, is to joke. Use the wink face emotion to imply a joke and to solidify the idea that your joking and probably getting a bit flirty.
Also, if the guy says something like... I like [something], a good way to be a bit jokey is by saying that... I like [something] more! I used to have this type of 'debate' with my girlfriend, but we realized that we both like it more than each other (Make sense?) ;)
Flirting on Skype would be different, if you are doing a voice or video call. It's mostly about the tone of your voice. Laugh and maybe include some sexual innuendo to the things he says. He'll probably see you more as a sexual being and consider having a relationship with you. He will probably realize that you are interested. If he's interested, I'm sure he'd flirt back. If not, then he's probably not interested. If anything awkward happens, just laugh it off and maybe say you're joking. He might know you're not, but who cares? Maybe he likes you too, but doesn't want you to know yet.
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