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Dear Prudence,

I’m a bisexual man in a happy, monogamous relationship. My wife is fine with my sexuality but does not want me to talk about it with other people. She especially does not want me talking about it around her friends, many of whom are gay men, for fear that they would start hitting on me. (I think maybe she also worries that they would make fun of me—although we all get along great.) She also does not want me to contact an ex-lover, who was also my best friend for a long time (although admittedly this was years ago). I’m not particularly bothered by these “conditions,” but I would like to speak to this guy at least once again in my life, and it might be nice to have people with whom I could openly discuss my sexuality.

—She’s Honestly Fine With It

I disagree that your wife is “fine” with your sexuality. If she wants you to keep your sexuality a secret and thinks any gay man who learned of it would be unable to keep from either mocking or trying to seduce you, I think she is in fact deeply uncomfortable with and resentful of your sexuality, which is a shame. It’s one thing for her not to want you to get in touch with an ex, which is understandable if high-handed; it’s quite another for her to forbid you from even talking about the fact that you’re bisexual. If she thinks the only thing keeping your friends from trying to destroy your marriage is a mistaken belief in your heterosexuality, then she has insufficient faith in both your marriage and the character of your friends. Tell your wife that you’re not going to hide who you are from those close to you simply to keep her comfortable. Her version of protection and support looks an awful lot like a closet to me.

* * *

Dear Prudence,

My roommate is a beautiful soul. Her wardrobe, not so much. She wears cheap, often tacky dresses (most of them with a “geeky” theme like Star Wars, Dr. Who, etc) all the time. Many of them are full-length ball gowns with petticoats underneath. Her employers appreciate her hard work and dedication, but I’ve noticed they never take her very seriously and she’s never been put in charge of the department she was trained to take over. I adore her geekiness and think style is personal and subjective, but I know not everyone else sees it that way. Her last boyfriend ended things after she wore an R2-D2 gown to his sister’s black-tie wedding, even after he begged to buy her a new dress. She rarely gets a second date. I have tried getting her to try on other clothes, but she seems uninterested. I think it’s entirely possible the outfits are a shield for her insecurity. I believe there is someone out there who will love her the way she is, but part of me wonders whether it’s time to sit her down and be honest because it’s holding her back professionally and romantically and she doesn’t seem to understand why. I’m worried I’ll lose my friend. Should I butt out or speak up?

—Say No to the Dresses

I know my answer should be something about how your roommate has the right to be her geekiest and most authentic self at all times, but I agree that floor-length Dr. Who–themed gowns are not always the appropriate choice for weddings or the workplace. That said, I’m not sure you’re best situated to talk to her about her fashion sense. You say her last boyfriend ended things because of what she wore to a wedding, so presumably she’s aware that her sartorial choices are off-putting to some—I don’t know what you could say to her that’s more effective than “You wore an R2-D2–themed dress, so we’re breaking up.” When it comes to work, your theory that her clothes are keeping her from being named director of her department is just that: a theory. You’ve already tried encouraging her to try other outfits and she’s refused to take the bait. It’s up to her employers to say something if they want her to dress differently at work, and it’s up to your roommate to find romantic partners who like her style. Despite your claim to love her sci-fi bent, I suspect you don’t like (and are perhaps embarrassed by) your roommate’s clothes and are looking for a justifiable excuse to call an intervention. You don’t have one.

* * *

Dear Prudence,

Please help us settle an office dispute. We have an employee, “Anne,” whose job description includes opening the office in the morning. She has three kids and a disabled husband, and is often late, leaving employees standing around outside in all kinds of weather. Anne is well-liked by employees and clients, and she fulfills all other aspects of her job beautifully. Unfortunately, she’s about to be fired because of her tardiness, which would negatively impact the entire company. One manager supports firing her, saying that opening the office is in her job description. Another manager wants to keep her on while changing her hours and letting someone else open the office. Manager X thinks that Anne needs to learn a lesson; Manager Y feels that compromising is more important than losing a good employee. What do you think?

—Carrying the Keys

I side with Manager Y—excellent employees who get along with co-workers and clients alike are hard to find, and Anne has some extenuating circumstances that may explain (although not entirely excuse) her chronic lateness. You don’t say whether either manager has ever had a conversation with Anne about how her tardiness affects the rest of the office. At the least, have a meeting where you seriously discuss her ability to perform her duties before your office decides to fire her. (I assume I’m addressing Manager Y.) If someone else is willing and able to take on the task of opening the office, freeing up Anne to come in a bit later, I agree that is a solution that benefits everyone and hurts no one. Job descriptions, like constitutions, are breathing documents subject to amendment. If, however, you accommodate her circumstances and Anne still can’t regularly make it to work on time at the new hour, it may be time to let her go.

* * *

Dear Prudence,

My in-laws last year asked if I could babysit their 11-year-old this April so they could go away for a weekend, which they never get to do. I agreed and told them I would just need a few weeks’ notice to organize my own child care around it. Well, it’s April, and they still haven’t picked a date. I haven’t been able to make any plans of my own for weeks, and as we get closer to summer, the heat affects my health condition and puts me at a higher risk for seizures. My in-laws definitely need the time on their own and don’t have other child care options (my niece-in-law is poorly behaved), so I would feel like a bit of a jerk withdrawing my offer. But I feel like they’re not being very reasonable. Is it fair for them to keep me on the hook, or should I tell them I’ll no longer be available?

—Babysitter Backing Out

You poor thing—I’m picturing you huddled in front of a calendar, sweating buckets, trying to stave off a seizure, while your in-laws keep pushing back the date of their getaway. “Oh, did we say the 15th? We meant the 23rd. But maybe the 30th. You’re still free then, right?” You promised them a weekend, not an eternal waiting period. They’ve had months to make arrangements with you. Make your own plans, tell them what weekends you have left open, and don’t let yourself feel guilty for a minute. If their schedule happens to coincide with yours, bully. If not, they’ll have to look for someone else (and think about solidifying plans further in advance).

* * *

Dear Prudence,

Last year, my husband and I went on our honeymoon and left a key to our house with my in-laws on the chance that something inside would need tending to while we were away. The whole time we were gone, I felt uneasy about them having a key and possibly looking through our personal items. Everything was fine, though, and they gave our key back when we got home. Fast-forward to our vacation last month. Remembering my feelings of unease, we decided against giving anyone a key. While we were away, my husband emailed his parents a few times and, in one of those emails, mentioned that we had forgotten to bring some plants over to their house for watering. Well, his dad told him that he had made a copy of our key while we had been away last year and could let himself in to water the plants! Prudie, I am beyond angry and feel that my trust has been irreparably damaged. Am I warranted to feel this way? How should I approach them?

—Katy Bar the Door

It’s reasonable not to want your in-laws to make a copy of the key to your house without asking, but I don’t think this was an irreparable breach of trust. You presumably never told your in-laws that you felt uncomfortable at the prospect of their having a key, and they obviously assumed they were doing you a favor by making themselves a backup—one that has suddenly come in handy. It was an overreach on their part, but it doesn’t sound like they’ve abused it or have made a habit of turning up uninvited and letting themselves in. If you don’t want them to have a key to your house, speak up. Tell them that you appreciated their having looked after things in the past, but you’d rather that you and your husband have the only set of keys and that you’d like them to return the copy they made. If they kick up a fuss, you’re well within your rights to have new locks made, but I don’t think your in-laws have demonstrated that they’re likely to be unreasonable about this. Give them the benefit of the doubt and assume this was a well-intentioned misunderstanding until they give you a reason to think otherwise.

* * *

Dear Prudence,

I work at a rewarding job with limited vacation time and make about half of what my sister and mother do (this will be relevant, I promise). I pay all my bills, but funds are limited for trips. Usually as a combined birthday/Christmas gift my family will help defray the cost of airfare or hotel to travel together. Now my sister is buying her first home, and my mother had to get a new car. The getaway is a no-go this year. I don’t mind that, but I do mind my sister’s assumption that I’d be happy to use my vacation to drive 300 miles to help paint and retile her new house! I love her and understand that buying a new home is stressful, but she gets six weeks of paid vacation, and I only get two! Should I bring it up, bite the bullet, or pretend to have a scheduling snafu?

—No Time Off

Your sister doesn’t seem to understand what a vacation is. It’s not “performing free home repairs in another state.” While it’s very generous of your family to help pay for your getaway airfare, don’t let that make you feel as if you have to devote your vacation time to an HGTV-style renovation. If someone makes an assumption you don’t like, it is incumbent upon you to correct said assumption—your sister might think it would be a fun project for the two of you, and you’ve got to speak up if you disagree. If you don’t want to spend your two weeks off helping your sister settle in, tell her you won’t be able to make the journey out this time, but you hope you’ll be able to get together soon.

* * *

Dear Prudence,

I work for a small division of a much larger company. We are physically separated from most of the company, so we’ve created our own little familylike culture—one that’s never felt very corporate. After my first year in a dream job, I was promoted to team lead. A year after, I was promoted to manager, and within two more years I achieved the title of director of my division. My family of co-workers was excited and encouraging of my quick ascension up the ranks, and many of them put my name in the running for each promotion! Where I’m struggling is how distant they’ve all become. They still smile and say hello, but I’m no longer invited to lunches, potlucks, or celebrations like birthdays or baby showers. My superior tells me this is life now and I’ll never get that back—that I’m to focus on the good I’m doing in my position and be thankful my division performs well above benchmarks. Do I really have to give up people for a position?

—Lonely at the Top

You don’t have to give up all people, just these ones. I assume the birthdays and baby showers are being held after hours and that you’re not being excluded from on-site celebrations. Most employees don’t spend a lot of time socializing with the people who have the power to hire and fire them (especially with someone who used to work beside them), and for good reason. The dynamic you’re describing is perfectly normal, healthy in fact. Be grateful you have a good working relationship with your subordinates, and look outside of your office for friendship.

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