Dear Dude Whisperer,
What do you think?
Offended(?)
Hi O(?),
It’s kinda like anything during sex that involves your anus. Dudes are gonna really roam the perimeter, ‘accidentally’ get real close, gauge reaction, lather, rinse, repeat, and then finally make some totally clumsy maneuver one night when they’re finally drunk enough.
Anyway, yeah. Normally a dude would not only totally take you up on the pictures, but ask if you took requests. “How ‘bout one like this? Okay, now lift this over here and put that like this and…”
First, while it’s true that on this blog the DW is over and over addressing situations where his advice could be summed up as, “Duh. Drop this dungsack of a dude. Now,” he does also like to remind his readers from time to time that there are, in fact, plenty of modest, shy, decent, thoughtful dudes out there. Really. It’s true. Now, is this dude necessarily one or all of these things? No. But if a dude was to make a list of Pros and Cons about accepting your boobie pics, there isn’t much to put in Con except some kind of moral objection. And in that case his nature is offended by the naughty picture part not the you part, if that makes sense. Nothing for you to be concerned about unless you simply can’t handle a dude so square.
Second, as you suspect, dude’s age might be an issue. 33 means he’s just old enough that MySpace and Facebook and everybody having a blog is a little foreign to him. He may not have had regular email access until he was 18 or 20 (which, the DW realizes, to his younger readers makes this dude sound Paelolithic. What else did he use? Rotary phones? Tape decks? Um, actually, he might have...).
Anyways, people maybe just 5 years younger than him might have a totally different idea of how much of their lives it is normal to have exposed to others. It's simply not as natural for a 33 or a 38 or a 42 year old dude to take a picture at a club and email it to half his friends from the cab on the way home. He might have way fewer pictures than a 22 year old dude posted on his online dating profile. He might wonder why in the hell someone would feel the need to Twitter about their current doings and whereabouts. You get the idea. So, you extend this different idea about, er, exposure, and it could seem a little odd or overly loaded with significance to get nudie pictures (that could be easily posted to the internet or sent to her mother, for god's sake!) from a girl you've been seeing for a couple weeks.
Best of luck working this saucy picture thing out to everyone’s satisfaction. Remember, too, you can just always ask the dude for an explanation. This certainly qualifies as uncommon enough that dude shouldn’t be surprised at a little confusion on your part.
Best,
the DW