09/20/2012 02:23 pm ET Updated Dec 06, 2017

eWise: Sexting Surprises, Overly Gchatty


What's the polite way to sext someone? I'm afraid that if I just sent him a full-frontal shot without warning it might be, well, an unpleasant surprise rather than a pleasant surprise. But then you don't exactly want to ask for permission since that spoils the moment. Thoughts?
- Clothed in Chelsea

If someone has you and your body on his mind, a nude sext should be a very pleasant surprise. But if you're still unsure where the relationship stands, it's probably not the best idea to test it with a compromising photo that could be distributed to your guy's friends or worse. Send him a clothed but flirty pic of you getting into bed and see what happens. If the response is less than enthusiastic, he may not be into you—and a surprise has nothing to do with it. Better to find this out now—before he has an archive of your topless self-portraits on his hard drive.

As any Seinfeld fan can tell you, there is “good naked” and “bad naked,” even for our loved ones. Male full-frontal pics, nude photos shot into a mirror with an iPhone and anything involving a duck face all tend to fall into the “bad naked” category.

A person that works for me and is otherwise a lovely human being comes off as demanding and sometimes overly familiar in online correspondence (emails, gchats, etc), sending many brief messages when one longer one might do, or a bit of investigation on that person's own part might answer the question. Am I being overly sensitive? Or should I ask the person to tweak their habits, and if so, how?
- Inundated and irritated, NYC

It’s too bad that screening for this sort of behavior isn’t part of a normal hiring process, but adjusting an employee’s communication style to fit your needs is just a part of being a good manager. This person sounds overly nervous about meeting your expectations and may be relieved when you set some boundaries. Next time your gchat starts blowing up, message back something like, “Can you look into this on your own and send the rest of your questions to me in an email?” Just forcing someone to go through email rather than gchat can result in significant self-editing. Take your time responding, or direct the more inane questions to

This story originally appeared in our weekly iPad magazine, Huffington, in the iTunes App store.