I am in a relationship with the most amazing guy in the world. He is sweet, funny, romantic, and amazing in too many ways to try to list in this letter. I am his first girlfriend, and he's my first serious boyfriend (I was his first kiss, and we were each other's first HND partner). We've been going out for just over a year, and I am as in love with him as I ever thought I could get.
There is just one thing that keeps him from being Mr. Perfect: he asks for pictures of me, a lot. Like, sexy-time-clothing-optional type photos. Sometimes we'll be chatting or texting and he'll randomly ask for something sexy, or it might be late at night and he'll ask because he's horny. He even asks sometimes when we're actually together, like in the middle of some heated making out he'll ask if he can take a picture with his iPod. He started doing this a few months after we started dating, and the first few weeks I went along with it. I'm really active in school sports (and he doesn't do anything after school) and it had been a week or two since we had been able to go out, so I felt bad and thought it was just a one-time thing. Some weeks later I realized that we'd been doing it for longer than I thought, and started avoiding it (telling him I'd already changed clothes, wasn't in the mood, was already in bed, etc).
We've had a couple of big fights about it, but after all is said and done nothing really changes. I've tried telling him that I'm not comfortable with it (he responds with the fact that my head/face is never shown therefore no one could ever know it was me), afraid someone will find them (he swears he hides them really well, and to his credit I've never been able to find them), afraid something might happen if/when we break up (he doesn't think we ever will, but we're seniors with vastly different plans for the future), among other legitimate reasons. His response is usually in the neighborhood of that he has needs too, and just because I don't get off to pictures doesn't mean that applies to him too. He also says that since I've sent him pictures before, I shouldn't have any problem with it now. The only problem is, I do. If I could go back in time and never send him anything, I totally would.
Auntie, I love this boy. I really do. We're really good about working through any other problems we've ever had (which are few and far between), but this is persistent and is driving me up the wall. This is a guy that I could envision spending the rest of my life with, and I don't want to break up with him over something as stupid as this, but I'd be lying if I said I hadn't thought about it. What can I do to make him stop?
Oh, for the love. Before we go any further, I just want to make sure we're clear: you know your "most amazing guy in the world" is acting like a complete heinous troll, right? And it's hardly stupid to be thinking about breaking up with someone who apparently values his masturbatory relationship with a picture of you more than his actual relationship with the actual you. This guy is pushing and prodding you to do something that he knows you aren't comfortable with, that you have legitimate and clearly-articulated reasons for objecting to, and that has no arguable benefit to you or your relationship. That's totally inconsiderate, and not a little disrespectful, and it would be weird if it weren't making you question things.
HOWEVER. Because this you're his first girlfriend ever, and because you've assured me that he is an otherwise reasonable and loving guy who only turns into a giant douchebeast under this one very particular set of circumstances, and because even the most entitled jerk should realize the error of torpedoing his real-life relationship with a girl for the sake of obtaining naked pictures of her, I'm going to allow for the chance that this dude genuinely doesn't realize how completely out of line he is.
Which, when you add in the fact that you were his first kiss and first girlfriend and first HND partner, actually makes a certain kind of sense—in the same way that it makes sense when someone binge-watches an entire season of Buffy in a single Saturday, or eats the same burrito from Chipotle twice a day for a week, or listens to Katy Perry's new single on a continuous loop without ever getting sick of it. It's New Favorite Thing syndrome: people discover something they really get a kick out of, and they become obsessive, myopic junkies until the novelty wears off. It happens with food, it happens with entertainment, and gross as it is, it happens with sex, too. So in this case, it's not impossible that your boyfriend's immense excitement at being able to OMG FOOL AROUND with an OMG GIRLFRIEND who can send him OMG NAKED PICTURES has caused him to fixate on the latter like a selfish, entitled weenie.
What you can do is deliver a reality check that'll snap him out of his single-minded focus on getting what he wants. Point out to him what he's apparently missing: that the whining and wheedling is such a turnoff, and such a dealbreaker, that you're thinking about breaking up with him. And don't couch it in milquetoast protestations that someone might find the photos, etc; the reason this is a problem is that it's making you feel like garbage, full stop. (Ex: "The fact that you keep asking me for pictures, knowing how I feel about it, says to me that you care more about jerking off to a picture of my body than you do about me. I've told you no, and I've told you why, and the fact that you won't respect my feelings is making me seriously regret that I ever sent you photos to begin with. Please do not pressure me anymore to do something you know I don't want to do.")
And then, hopefully, you can have an actual discussion about this instead of a fight. Maybe your boyfriend will be sobered by the realization that he's acting like a digital date rapist. Maybe you can reach a compromise in which you send him occasional photos, only when you're comfortable with it, using a privacy-protecting service like Snapchat. Maybe you can point out that if he "needs" pictures of boobs to get his rocks off, the internet is a thing that exists.
Or maybe he'll keep acting like a heinous troll, and you'll drop him like a hot potato. You'd be entitled.
Does your SO hound you for naughty pictures? Tell us in the comments! And to get advice from Auntie, email her at firstname.lastname@example.org.
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