I'm sorry - I TOTALLY disagree here.
If someone told me my pic was 'boring', there is absolutely no way I'd be like 'ooh okay, well then I better strip down and show you'. Definately not.
As for your 'rules'
1. I agree with.
2. You're a dumbass (no offense!)
3. You're even more of a dumbass. 'see what you got?' dude.. nooo...
If you REALLY wanna try to get a girls nudes try playing a game with her. Of course you gotta flirt your ass off first then ask if she wants to play truth or dare. Ease into it.. then say something like 'i dare you to send me the sexiest pic you've got of yourself'. If she says no be like 'hahah alright it's cool, it's not like all your pics arent sexy
' keep flirting.. then try again a little later.
If she sends you one and she's not nearly naked say something like 'babee thats hott' (or something encouraging), then later in the 'game' dare her to send and even sexier pic
If she's not down.. you'll know right away. Just make sure you're very complimentative and confident. Don't be a prick.
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