Dear Prudence

The Story of Oh, No

My boss walked in on me touching myself, and now he won’t stop flirting. What do I do?

Emily Yoffe.

Emily Yoffe

Photograph by Teresa Castracane.

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Dear Prudence,
I’ve worked for the past five years as a night security guard at a large indoor facility. Typically there are three of us on the overnight shift: the supervisor, “Charles,” with whom I’ve always had a cordial relationship, another guard, and myself. (I am the only female.) One night I went to a bathroom I don’t usually use, was overcome with a very strong sexual urge (as often happens with me), and began to masturbate. The toilet seat was uncomfortable, so I decided to sit on the tank. It turns out the lock on the door was broken, and before I was through, Charles walked in on me. I shouted at him to get out but it was several painful seconds before he did. I expected to be fired and was prepared to beg him not to let me go, but instead I had to endure a lecture about the merits of controlling oneself and finding the proper time and place to handle “such things.” He then offered the use of a special room in the building where I could “take care of business” if ever I felt “the urge” again. I declined. Since this incident the other guards I work with in rotation have all been giving me knowing smiles and making thinly veiled comments letting me know they know. Charles has become very flirtatious and thinks he now has license to speak to me in an inappropriate manner. I understand that I brought this upon myself, but I have children to support. I can’t afford to lose this job. How can I remain employed and re-establish the professional relationship I once had with Charles and my fellow guards?

—Not Taking Care of Business

Dear Not,
The best thing for a supervisor to do if he accidentally walks into a bathroom and discovers a subordinate ecstatically riding the toilet tank is to turn, mumble, “Excuse me,” and flee. There you were, caught pink-handed, and now Charles thinks that has given him carte blanche to act out a blue-collar version of Fifty Shades of Grey. You now know that no matter how horny you are, you should wait to relieve such urges in the comfort of your own home (although a similar situation made for a much-discussed scene on a recent episode of Girls). What you did demonstrates poor judgment and was a mistake. What your boss is now doing demonstrates sexual harassment and is illegal. I spoke with Philip J. Gordon, a Massachusetts employment attorney, and he said that employees using the bathroom at work have a reasonable expectation of privacy. Your supervisor’s violation of that was accidental, but as a result, he is deliberately turning you into sexual prey, just because you may have listened to Britney Spears’ “Touch of My Hand” too many times.

Charles should not have offered you a masturbation lair (complete with security camera, we can assume). His next mistake was telling all the boys and allowing them to participate in a snicker fest. Now he appears to be making an implicit bargain: Put up with his smarmy innuendo and you get to keep your job. This is against the law, Gordon says. You may feel you brought this upon yourself, but you didn’t. If a woman dresses in what could be described as a sexually alluring way, it does not give her male colleagues license to create a hostile work environment. Your boss seeing you touch your private parts in a private setting did not turn the facility you guard into the Playboy Mansion. So now you need to address this. Sit down with Charles and calmly tell him that the atmosphere at work has taken a very unpleasant turn and it’s time for it to stop. Say what’s happening is no longer a joke, it’s sexual harassment (emphasize that phrase), and he needs to make sure everyone goes back to treating you as a fellow professional. That might take care of it. If it doesn’t, after a few weeks, reiterate the conversation in an email to Charles. Then, if after a little more time the lewd comments don’t end, forward the email to Human Resources and ask for an appointment. You can simply tell them that Charles walked in on you in the bathroom, and since then you have been the object of endless crude remarks. If Charles wants to explain that his behavior comes from seeing you masturbate, he will find out how that works as a line of defense.


Dear Prudence: Double Ds and a Jealous Friend

Dear Prudence,
My son is finishing his junior year of high school. His grades are average and have slipped each year. His study habits are poor. His teachers say he “has potential” and “is intelligent” but he just doesn’t apply himself. College is coming up, and his father and I dragged him to see two universities. He wasn’t that interested but said he is fine attending either one. One is a state school that would cost us approximately $24,000 a year, and the other is a private university costing around $30,000. I just don’t see having him having the appropriate skill sets to handle college. I’d hate to spend all that money and not have him do his best. Both my older brothers flunked out of college, so maybe boys in my family just aren’t ready for college at 18. When my husband and I try to talk to him about this, our son says we are making it all about the money or we’re too critical. He says there are kids with worse grades and their parents are more supportive. I think we are supportive, but I want to spend our hard-earned money wisely. I want to speak to him without confrontation. What should I do?

—It’s Not All About the Money

Dear Money,
It’s not all about the money, but it’s a lot about the money and fair enough. Your son is fortunate that his parents can pick up the tab for a college education and not make him start out his adult life like so many of his cohort—with an onerous pile of college debt and no income with which to pay it off. I also agree that the prospect of funding advanced bong studies to the tune of around $30,000 a year is not a promising investment. You and your son are going around one of those loops that sometimes define life with a teenager. But you can get off it. Say that with college deadlines looming, part of demonstrating that he is ready to go is stepping up and taking responsibility for his applications. Tell him you and your father will be there to help him whenever he needs it, but you are not going to micromanage and nag your way through this process. You can say that if he’s not ready for college, there’s no shame in that. Taking a break between high school and college and working for a while is a reasonable decision. Then step back and let him make his choices. It could be that a dose of the real world will be the best source of motivation for getting him to continue his education.


Dear Prudence,
My son married a wonderful girl a few years ago, and they just had a baby boy. His wife has a daughter from a previous relationship, and my son has another son from a previous relationship. These children are the same age and get along well. My daughter, too, has a son who’s older, and my husband and I are looking forward to taking him to Mexico this year as a graduation gift. We would like to take our other grandson (my son’s first) as well. But I am torn, as we love our step-granddaughter and she calls us Gran and Gramps. But I really want to spend time with “my” grandsons, and taking her would cost $300 in airfare. Our step-granddaughter has her own loving grandparents who spend time with her. How do I break it to them that I want to take only my grandsons? I believe my son would not have a problem with it, but my daughter-in-law and step-granddaughter may. Am I wrong?

—Grandsons Only

Dear Only,
Your step-granddaughter may have more than her allotment of grandparents, but how it will sting to have Gran and Gramps come to pick up her brother and leave her behind. Sure, adults can explain the difference between blood relatives and the other kind, but when stepchildren are lucky enough to be brought into loving new family, they stop feeling like the other kind. As your son’s baby grows up, you will want him to adore his older brother and sister, not think of them as having asterisks because they’re not his full siblings. Shelling out $300 seems like a small price to pay to make clear that no matter how they got there, you don’t make distinctions among the people who call you Gran.


Dear Prudie,
I wrote to you a few weeks ago about a creepy math tutor who had behaved inappropriately toward me and other teens. I wanted to let you know that after mustering up my courage, I contacted the police and was pleasantly surprised at how promptly and seriously they responded. They took both a written and recorded statement, and were very detailed (and sensitive!) in their questions about the incidents. They also interviewed the teens whom the tutor approached this year and took their statements, as well. To my utter shock, the police also informed me that after running the tutor’s name through the police database, it turns out that you were right—he really did have a prior history of inappropriate behavior. Though neither my complaint nor the others’ are major enough to warrant any charges so far, the police commended me in helping put yet another piece of the puzzle into place. I am now telling parents to pull their kids out of his classes and to ask their kids if he’s done anything untoward to them. Because I finally reported him, he is just that much closer to being caught.


Dear Relieved,
Thanks so much for this update and for letting us know how valuable it is to report such incidents. Even if a single case is not actionable, you can help the authorities put together a file that might stop such predators.


Discuss this column with Emily Yoffe on her Facebook page.

More Dear Prudence Columns
A Minor Flaw: I’m dating a man who was charged with soliciting a teen for sex; I wish I’d never discovered this!” Posted July 28, 2011.
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Almost Famous: My rock-star ex wants his sexy photos back. Should I relent or play hardball?” Posted July 14, 2011.
 “An Innocent Man: An ex-girlfriend falsely claimed I raped her. How do I reveal this hurtful incident to future love interests?” Posted July 7, 2011.

More Dear Prudence Chat Transcripts
Confronting the Queen Bees: Dear Prudence advises a teen who longs to stand up to her cruel classmates but fears retaliation—in a live chat at” Posted July 25, 2011.
Bozo Boyfriend’s Nose-Job Nightmare: Dear Prudence advises a man who convinced his girlfriend to have plastic surgery that left her disfigured.” Posted July 18, 2011.
Should a Former Hottie Burn the Evidence?: Dear Prudence advises a woman whose ex-husband took nudie pictures of her and still has them—during a live chat at” Posted July 11, 2011.
Boyfriend Is Thick as a Brick: Dear Prudence advises a woman who is reluctant to wed her dim-bulb suitor—during a live chat at” Posted July 5, 2011.