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My boss/CEO lives and works in a different city, but most of her mail arrives at my office because it is the company's official address. I routinely open mail and packages addressed to her. Usually they contain documents or software, but today I opened a package to find something completely different: a pair of vibrating panties.

Both the billing address and shipping address are the same, so I'm guessing she purchased them on her company card.

I know this is more of a business-etiquette question, but do your amazing sex-advice skills provide you with any ideas on how I should handle this? It will be very obvious that the package has been opened, even if I try to tape it back up and send it to her home address. But if I do nothing, she's going to wonder where her shipment is.

We're a small, casual company and she's a pretty confident and outgoing person, but I can't really predict how she will react to this. Would it be weird for me to just be up-front about this situation? Should I just throw in a sticky note that says, "Whoops! Have fun! J" and send it on?

Avoid The Awkward


Emoticons are never the right answer. Please make an emoticon-free note of it.

Now here's what my amazing sex-advice Spidey sense is telling me: Vibrating panties are not a sex toy. They're a gag gift. Check your boss' schedule: Any bridal showers coming up? Bachelorette parties?

There's a small chance that your boss doesn't know much about sex toys and purchased a pair of vibrating panties to wear on long flights (if she can get them past security). But you should treat this pair of panties like a misplaced gag gift, and not an existential workplace crisis. So no notes, no emoticons, no being "up-front about this situation," because this isn't a "situation." It's a shipping error.

Tape up the box and send it off to your boss and forget about it. If she feels a need to bring it up -- if she wants to apologize or let you know it was, in fact, a gag gift -- she'll bring it up.


Yesterday I was finishing a work conversation with my boss via instant-message from my home computer. I meant to send her a legitimate link, but because I used the wrong combination of keys, I accidentally entered a several-day-old porn link that was still in the memory and hit send before I noticed my mistake. I'm a 30-year-old male, my boss is a few years younger and female, and she's generally cool. Once I realized what I had done, I immediately told her not to click the link and I sent the right one. The URL left little to the imagination about what kind of link it was.

We work in a very professional environment that's careful about maintaining a harassment-free workplace. I'm horribly embarrassed. How should I handle it?

Jerk From Home


Workplace power dynamics being what they are -- bosses can fire employees -- you need to put something in writing.

First, no emoticons.

Second, send a brief e-mail to your boss detailing just how that happened -- IMing from your home computer, not your work computer (making it clear that you weren't looking at porn on your work computer without using the word "porn") -- apologize one more time, and state that you'll take care that it doesn't happen again. You could still get in trouble with HR if your boss decides to make a case of it, but you'll be able to point to a contemporaneous e-mail that details your side of the story, i.e., an accident, you weren't rubbing one out in front of a work computer.

In somewhat-related news: Today I sent my straight boss a picture I found online of a guy with a wine bottle stuffed up his ass -- I did it on purpose. ;)


I wanted to thank you for drawing so much attention to Sex at Dawn. I am going to get it as soon as possible so I can better understand myself. I have always felt a certain amount of shame because I've never had a monogamous relationship. Having been married 14 years (married at 19, which I know is a no-no in your book), I've had plenty of temptation and only given in a few times. Those events felt like they were saving my sanity; they never had anything to do with me loving my husband any less. For all these years, I felt like shit because I couldn't be monogamous. Thanks for cluing me in to evolution, reptile brains, etc.



Thanks for the nice note, M. Now go forth and cheat no more, i.e., don't be a CPOS (cheating piece of shit). If you're incapable of being monogamous, don't make monogamous commitments.

And to all the outraged folks writing in to ask if I'm suggesting that no one should ever be monogamous: That's not what I'm saying, and it's not what the authors of Sex at Dawn are arguing, either. The point of Sex at Dawn isn't that no one should attempt to be monogamous, or that people who've made monogamous commitments have a license to cheat . There are lots of good reasons to be monogamous -- e.g., children and other sexually transmitted infections.

What the authors of Sex at Dawn believe -- and what I think they prove -- is that we are a naturally nonmonogamous species, despite what we've been told for millennia, and that is why so many people have such a hard time remaining monogamous. I'm not saying that everyone has to be nonmonogamous; the authors of Sex at Dawn don't make that argument either. (Lots of monogamists, however, do run around insisting that everyone should be monogamous -- and proscriptive monogamists get a pass because, hey, they mean well, and wouldn't it be nice if everyone were?)

The point is this: People need to understand why being monogamous is so much harder than they've been led to believe. This understanding may help some people seek out nonmonogamous relationships and/or arrangements and/or allowances that make them -- gasp! -- happier and make their relationships more stable, not less, as a routine infidelity won't doom their marriage/civil union/commitment/slavecontract/whatever. But understanding that monogamy is a struggle for most people -- and being able to be honest with our partners about that -- may actually help some people remain monogamous.


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