Ask A Guy: What To Do If A Guy Asks You To Send Him Nudes

Hey Joel,

So I’ve been talking to this guy for a few days now. I am starting to like him and I think he has the same feelings. But last night we were playing a game of Twenty Questions and he asked me my boob size, if I masturbate, and if I watch porn. Then, he asked me if I would send him “pictures.”
I answered the questions (and ignored the part about pictures) but was confused why he wanted to know and felt gross afterward for telling him. I like him, but I don’t like that he asked me that. I feel like these are classic f**kboy questions–is there a good way to avoid them in the future?


First and foremost, regardless of circumstances, you should NEVER feel obligated to answer any question that makes you feel awkward (unless you’re in court). Even if you’re just being silly and playing a game like this, if you’re uncomfortable with the conversation, don’t have it. If he starts saying it’s no big deal or that you’re being a prude, that’s his problem. You have a right to privacy or just not answering, so moving forward, take a pass on these questions.

Insofar as making a character judgement based on his rather blunt questions, I’d say that at best, he’s just looking for some action and not a relationship. At worst, anything you say to him or send him could be shared amongst his friends. Any guy with even the least bit of class would know that this sort question is far from off limits, especially when you’ve only been talking for a few days. To me, his intentions are clear: he wants an “easy” girl, and nothing beyond that really matters.

There is something to be said for mystery and anticipation, and learning about the details of your body is not information for just anyone. I mean think about it: if he asked you about your size, he’s clearly looking for a specific answer that is “acceptable” to him. That in itself should be enough to cut this guy off, but the fact that he pressed for even more intimate details tells me that he has no tact, and will likely treat you poorly, and then tell these intimate details to his friends to look cool.

I cannot stress enough how important it is to remember that your body, your habits and what you talk about are completely your own business. Nobody should force you to talk about personal things that make you uneasy, and nobody has a “right” to know your intimate details. If some guy does that to you, he’s probably not looking for a relationship, and his next step is likely to ask you for some nude photos. Guys like this are easy to spot and are not worth your time, plain and simple.

Best wishes,


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

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