Can I kiss you? Never ask. Assuming you’re on a date and the circumstances are right, just go for it.
Why won’t you talk to me? Weak! Concentrate on being a better guy to talk to. Alternatively, focus your energy elsewhere.
You look different today, why’s that? Whether she does or doesn’t, this question lacks tact and is unlikely to go over well.
You’re looking tired today, did you not get a good night’s sleep? Unless you’re making a sarcastic joke due to inside knowledge (which could go over well) this just unnecessarily makes the girl feel self-conscious.
I know you’ve got a boyfriend, but can we be friends? This comes across fairly sleazy and you can be guaranteed the girl will be questioning your intentions.
How old are you? It’s an old cliché, as well as chapter one of the gentleman’s handbook. Never ask a woman her age.
I don’t know, what do you want to do? Every girl wants a guy who will be the man and lead with a decision.
Is that what you’re going to wear tonight? Implication: that looks terrible, what were you thinking? Unless your girl is completely off the mark on dress code, this is a risky line to take, boys.
Are you pregnant? The question she hears in her head: have you put on weight? You don’t need me to tell you why this is a bad question.
How many guys have you been with? You don’t really want to know so why ask?
Is your sister attractive? Be a gentleman.
Are you on your period? This is a weak and way-too-mainstream way of challenging her on her attitude. Be more articulate.
Can I borrow some money? How to turn a girl off in 5 words. Women seek providers, not parasites.
Do you think I’m attractive? Even weaker! Guys who are confident in their appearance would never ask this question. Neither should you.
How much do you weigh? Chapter two of the gentleman’s handbook. Never ask her how much she weighs.
Why do you like wearing [insert piece of clothing]? Don’t ask judgmental questions like these. Think of something better to say.
Are you in love with me? If you feel you need to ask then the answer is probably at the N end of the spectrum.
Why are you friends with [insert name]? People maintain relationships with different people for various reasons. Questioning a woman’s friendship with someone is a sure sign of insecurity on your part.
Why are you single? This isn’t a terrible question, and if it’s delivered in the right way it can come across as flattering. The problem is, it puts the girl on a pedestal which isn’t smart from a dating perspective.
Are you really going to eat that? Unless this is said in a playful way, hold off on the food judgment.