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I don't like these, I'm not there to tell jokes. The only one I'd consider using is the Tony the tiger one because it doesn't come off as a standard joke/punchline affair and its got some back story to it that doesn't make it seem like you're just plain odd/don't know how to talk to women.
I get that you're probably not the joking type and that's okay. But I wanted to help out the people who had a more playful personality. Hence, the title of the post was "Funny Questions To Ask A Girl" and not "Serious Questions To Ask A Girl."
Also, joking doesn't imply that you're odd or don't know how to talk to women. Making a girl laugh is an art form and it can be a great ticket to successful pick ups. It's all about knowing when to use these questions because they aren't all meant to be used as just openers.
On the contrary, I'm very playful and I didn't mean that joking was synonymous to not knowing how to talk to women. I just don't like the standard question/punchline nature of some of these jokes e.g. 3 and 4.
"Would you rather" comes off to me as someone desperately seeking conversation and I'd probably find an excuse to leave if someone brought such a thing up in conversation.
My problem with question 5 is that it comes across as insecure: not only are you asking permission but you're making a joke as though to excuse yourself for asking permission. It's sort of like "please let me talk to you, I might be able to give you a few laughs... PLEASE!"
Maybe it works for you and if so, that's cool but I wouldn't consider using most of these myself.