Dear Prudence,
I am a professional man who is generally confident, but I am wondering about the etiquette of asking my dentist on a date. I have always felt that it is unfair to put someone who works for your business in the position of having to decline your advances, so I have never made such an attempt. But recently I have become attracted to my dentist. She is funny, kind, charming, and despite being a fan of a horrible professional football team, seems to be a wonderful person. Of course I know that my interactions with her up to this point are very limited, but that is true of all relationships at some point. So, is it OK to ask, or do I just have to hope I run into her in the grocery store one day?
— Drilling
Dear Drilling,
It’s a tribute to her skills, or your teeth, or both that you find yourself hoping to get her fingers out of your mouth so you can get to know her better. Of course, when you have a saliva ejector hanging off your lip, you’re not at your best, so it’s good you haven’t said anything while trapped in her chair. There is no reason you can’t ask her, but depending on her romantic status, her reaction to you, and her views of proper dentist-patient interaction, be prepared to be turned down. I looked up the American Dental Association’s code of ethics and conduct and on relationships with patients it says: “Dentists should avoid interpersonal relationships that could impair their professional judgment or risk the possibility of exploiting the confidence placed in them by a patient.”
That sounds like a lot of leeway, so ask away. The problem is that professionally you only see her twice a year, so I suggest you write her a note — with a big “Personal” across the envelope, and send it to her office. You can explain that not only is she a fabulous dentist, you find her a delightful person. Say that you’d enjoy getting to know her better over dinner one night — you can mention you are more presentable when not wearing one of her disposable bibs. Give her your email address and say that you hope it’s a yes, but if for whatever reason she can’t take you up on your offer, you look forward to seeing her for your next check-up and you will continue to floss daily.
— Prudie
Dear Prudence,
My husband and I are planning a vacation to Hawaii. One of my friends has been feeling very lonely since she broke up with her boyfriend, and I’ve been spending a lot of time with her to be supportive. She recently informed me she’s coming to Hawaii at the same time we’re going to be there and is staying at the same hotel! She’s very excited about the vacation and wants to know exactly what activities my husband and I are planning, presumably so she can come along with us.
I’m really annoyed because this is supposed to be a chance for my husband and me to spend some quality time together. I’ve been dropping a lot of hints about how busy we will be, and how we won’t have time to spend with her. I’m also emphasizing how much things are going to cost. (My friend is strapped for cash.) However, she’s not getting the message and she’s already made hotel and plane reservations! What should I do?
— Three’s a Crowd
Dear Crowd,
Maybe the boyfriend broke up with her because she is clingy as a barnacle and has as much social sense. Native Hawaiian wildlife is under threat by invasive species, and your tropical romantic getaway is also in danger because of an intruder. Before you find your friend sitting in the middle seat between you and your husband as you all take off for this threesome, stop hinting about what a pest she’s being.
Sit her down and tell her how upset you are that she’s invited herself on your vacation. Explain this is a long-planned trip for you and your husband to have a romantic time together, and you don’t intend to make it a trio. Say of course you can’t prevent her from going to Hawaii, but you’re not going share your schedule with her because you don’t intend to share your vacation with her.
If she can’t take the financial hit and cancel the tickets, then she needs to start planning her own activities. You can also say it might be less awkward if she stays at a separate hotel so you’re not always running into her in the lobby. If she can’t figure out how to enjoy herself alone on vacation, she can always swim up to the poolside bar and drown her sorrows in Lava Flows.
— Prudie
Dear Prudence,
I work at a small nonprofit of about 20 people, most of whom are under age 35. Our president is a big personality and often tries to treat employees as friends, whether they like it or not. She makes jokes that are highly inappropriate and she bullies our more timid employees. Last week she took things to a whole new level. In an attempt to scare a female employee who’s been the victim of some of her bullying, she snuck up behind her and planned to give the employee a soft tug on her skirt. What actually happened was that the employee’s skirt came off her waist and exposed her underwear.
Immediately afterward the president repeatedly told the depantsed employee “not to tell anyone.” The employee did go to speak to a high-ranking executive officer about this and the bullying. Later that day the executive went into the president’s office and, leaving the door open so we could all hear, casually brought it up. The president has profusely apologized to the employee, but as far as anyone can tell she has received no disciplinary action.
Would it be wrong to tattle about something that didn’t happen to me? Or should I just butt out of what is not my business?
—Caught With My Pants Down at Work
Dear Caught,
You say the president is a big personality, but she could more accurately be described as a big personality disorder. Someone who strips her subordinates—even accidentally while trying to simply intimidate them—should be stripped of her duties. Perhaps your boss, because she works for a philanthropic organization, suffers from the kind of moral hypocrisy described here— she thinks she’s making the world a better place, so that allows her to behave horribly while doing it. More likely, she’s just the latest entry in the series of letters I’ll title: How Did That Nut Get That Job?
What happened to your emotionally battered colleague is not a singular transgression—your boss is a walking human-resources violation. I have the strong suspicion that inappropriate jokes, bullying, and disrobing of subordinates violates the company manual and her terms of employment.
Everyone who works there is affected by the boss’s unprofessionalism, so speak up! But given that these are desperate times, it’s likely you will want to make your observations known in an anonymous letter. Describe the many misbehaviors of your boss, including the skirt caper, in a dispassionate, factual way. Say that the president’s misconduct is undermining morale, violating the organization’s mission, and potentially creating grounds for a lawsuit. Send a copy to all the top executives and the members of the board.
If your boss isn’t then either reformed or gone, get your own résumé out there.
— Prudie
Please send your questions for publication to prudence@slate.com. (Questions may be edited.)