How to flirt over texts?

Everyone says excess smilies and winkies, but I feel like I want an actual conversation.

Would it be weird to say, "You should send me a picture of your studly self" or something along those lines? D:

He's kinda inexperience to the whole scene of dating and stuff, so I don't know how to proceed. Help :(


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  • Play a game.

    You could start with an introductory, 'Have you ever..." There are all sorts of ways it could go. Funny, deep, kinky...just be playful and don't take it too seriously. :D