Dear Prudence

Help! Is My Couch-Surfing Sister Using Us to Make a Fortune on Airbnb?

Read what Prudie had to say in Part 2 of this week’s live chat.

A woman sleeps happily—a thought bubble indicates she's dreaming about money.
Photo illustration by Slate. Photo by Thinkstock.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Q. Beach house: My sister makes most of her money renting out her beach house during summer, when she usually stays with her boyfriend or our parents. This year, she got offered an indecent amount of money for the month of December and wants to spend two weeks with my family. She offered to pay her way, but the amount is less than three days of what she is renting her house for. My husband and I accepted her initial offer without looking at her actual finances. My husband caught a look at some of her emails while we were over at my parents, after my sister didn’t log out of her email. Now he is furious and wants to demand more money. I am afraid of embarrassing and enraging my sister. Beyond the violation of her privacy, we have hosted my in-laws for a far longer time and never asked for money. How do I work with this and not explode my family?

A: If your husband wanted to ask for more money in order to make her offer a fair market rate, that would be one thing, but it sounds like he’s just upset that she’s gotten a good deal on her own house and feels entitled to a cut of the action. Moreover, the fact that he spent long enough in her inbox to get a sense of how much money she’s making suggests this wasn’t an errant Whoops, saw a subject line and read a few sentences before realizing this wasn’t my account, but that he saw something that piqued his interest and decided to go snooping. Forget what you saw, encourage your husband to stop snooping, and reconsider whether you actually want to take her money. If you normally host family members without asking for help with the rent, why would you make an exception for her just because you snuck a look at her finances?

Q. Not so happy hour: After over a year of searching, I finally started my dream job at a tech startup. The role will no doubt help me grow professionally, as well as regain some financial security—I was almost flat broke before I received my first paycheck. Here’s the problem: I am not big on drinking with co-workers. I believe that co-workers should be work associates and nothing more. But after a few short months in the role, it’s clear that socializing—read: drinking—is a key element in the role to get ahead and network. So much so that we have happy hours during work hours, and after-work drinks at events that aren’t optional. I’ve felt uncomfortable in this type of environment to begin with, but at a recent work event, one of my supervisors called me something incredibly sexist and offensive—and no one spoke up in my defense. I was dumbfounded. I don’t know how I can respect or work with him after this incident. And since he’s my supervisor, I didn’t feel comfortable confronting him in front of my co-workers, or at all, due to the power dynamic. I’ve bounced around to a few different roles in the last several years, and I really need to settle in somewhere in my field or else employers might think I can’t hack it in one place for the long term—it’s already been a topic of interest in past interviews. Should I let this go, put my head down, and keep forging ahead? Or is this a sign to get out, and fast?

A: If your company has an HR department, or if your supervisor has a boss you feel comfortable talking to, I think it’s worth going on record as saying, “My supervisor called me a really offensive, sexist term during a recent work event, and I’m not comfortable with it.” It’s terrible when the person you’d normally turn to for help with workplace harassment is the person doing it, so if you don’t feel like you can safely bring it up, then looking for another job might be your best option. How awful, too, that no one else spoke up in your defense in the moment. It’s my understanding that in order to prove someone is creating a hostile work environment, more than one instance of harassment is necessary, but you should certainly document that incident and any others that may arise in case you need to consider your legal options. I can understand your concern about having had several jobs in recent years, and I can also imagine that you might not want to say in an interview, “I left my last job because my boss called me a gendered slur.” If you have any co-workers you trust, or who seem equally uninterested in the mandatory drinking-and-insults culture your company is trying to foment, you might consider talking to them before the next event and suggesting that the two of you look out for each other and maintain a slightly different dynamic.  

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Q. Sexy too soon: My 12-year-old stepdaughter just hit puberty and is extremely uncomfortable about her body. She drowns herself in her brother’s sweatshirts and tries to make herself as small as possible. It doesn’t help that her mother treats her like a Barbie doll. If it is tight, low-cut, or garish, her mother loves it. They are constantly in conflict over my stepdaughter’s wardrobe. I have tried to stay out of it and to put some sensible rules down, like “No wearing pajamas in public” and “Clothes must be clean with no holes.” Then I witnessed a fight where her mother said, “You are never going to attract any boys looking like that” and “Why do you want to be ugly? Because that is how you look right now?” to my stepdaughter as she cried. It made me sick to my stomach. My stepdaughter thrives when she is with my husband and me, even her brother remarks that she is happier and more open here. So far this isn’t affecting her grades or extracurricular activities, but I am worried. I also don’t think that getting into a custody battle with my husband’s ex is going to help my stepdaughter. How do I bring up my concerns to my husband? What should we do? He is much closer to his son and is unsure what to do with a teenage girl. Am I overstepping?

A: Trying to help a 12-year-old girl who’s being verbally abused and overly sexualized by her own mother is not overstepping. Your husband may feel lost at the prospect of parenting his daughter, but he’s going to need to move past that. It’s not baffling or impossible to guess what she needs right now: namely, a parent who supports and affirms her and who intervenes when someone else spits venom at her, even if that someone else is her mother. Tell your husband exactly what you’ve told me—that you’ve seen your stepdaughter reduced to tears because her mother has told her that it’s her job, at 12, to dress to attract boys, and that if she doesn’t she’s “ugly.” You two need to make sure that your stepdaughter knows that what her mother is saying is cruel and untrue. You also need to make it clear to her mother that if you see that kind of behavior from her in the future, you’re going to intervene. This is worth getting into conflict over, and your husband will need to find ways to get closer to his daughter so that he can protect and support her.

I’m so glad that she has you in her life, and to whatever extent you can model an adult woman who doesn’t bully preteens for her, you’ll be doing her a great deal of good. Let her know that she can come to you about anything, that in your house she can wear whatever she likes (I’d encourage you to not think of wearing large sweatshirts as “drowning herself”—that’s an awfully dramatic way of making it sound like she’s erasing part of her identity by wearing an oversized hoodie, and implicitly reinforces the idea that the shape of her body is the truest thing about her), and that you’re going to stick up for her when her mother tries to abuse her.

Q. Re: Beach house: Don’t compare what the sister is paying to what she is making. The right question is whether what she is paying approximates your costs in hosting her. Hotels don’t charge for rooms based on the customer’s income; they charge what the room costs them plus some profit. Back in the 1970s, my mother, a public school teacher, and I, a college student, stayed at an inn in Concord, Massachusetts. We later read that Jacqueline Onassis had stayed there while visiting her daughter at her boarding school. She probably stayed in a nicer room than we did, but I’m sure the inn didn’t raise the price of the room for her.

A: Right! The real issue here is that your husband is clearly upset your sister is making money on her beach house. The answer to that is Work through your own feelings about family and income, not Start charging her for things you used to do for free. (The other answer is, Stop reading other people’s emails.)

Q. Fake lesbian: I am asexual. I’ve always been this way, but people often try to label me as “frigid” or “broken.” “Alex” has been my friend since high school and is basically a hound dog. He serial dates but tends to get bored easily. I am his oldest and only long-term female friend beyond the wives and girlfriends of our mutual social circle. We are an odd couple of roommates, but in a brutal rent market we get along and don’t drive each other crazy. Alex crashed and burned his only serious relationship last year and has returned to high gear dating random girls he finds wherever. When I wake up to make coffee, there is often some stranger in my apartment. I am tired of dealing with random jealousy and invasive questions from these girls. A few times I have been sucked into drama because they begin to see me as a girlfriend or threat. So I lie and say I am a lesbian. I wear enough flannel to pull off the stereotype, and it saves me so many headaches. I feel guilty about this, because my gay friends have suffered a lot with their sexuality and coming out. I am just trying to avoid conversations with my roommate’s one-night stands. Does this make me a bad person? Is OK to lie to here?

Alex might be a lousy boyfriend, but he is an amazing friend. He drove me through a literal snowstorm in college when my grandmother collapsed. I have never found fault in the way he treats me—he’s just not a good boyfriend. He woos relentlessly and breaks up over minor issues. Alex and I work well together as friends and roomies and are likely going to be living together until we make enough money to buy our own places.

A: You say he’s an amazing friend, but it sounds like Alex is perfectly happy to let these one-night stands treat you rudely without intervening when they ask you invasive questions. That’s not amazing, especially since it happens over and over again. I don’t think you should feel guilty for making up a convenient fiction in order to stop getting harassed over your morning coffee, but Alex should feel like a real louse for treating all the women in his life like means to an end. Tell him that this isn’t working for you, that the girls he brings over may not be potential long-term girlfriends but that he needs to be honest and upfront with them about having a female roommate, and that he needs to have your back if they speak rudely to you. The only hypocrite here is Alex—he’s convinced you that you’re the exception to the women he treats badly, when in fact he’s being just as cavalier and flippant about your feelings as he is about the girls he brings home.

Q. Boyfriend isn’t out … completely: I’m a recent college graduate who started a relationship with a guy two years my junior. When his family came to visit our college, he came out to his mom and sister and told them about the relationship. I also told my parents (as they headed home, to avoid a scene). It’s been a year since then, and he still hasn’t come out to his father. I’ve tried bringing it up, but he doesn’t want to push the issue. School has started again, and his parents are planning to visit in the next few weeks. I work in our college town and will likely see his family at my food service job. How do I navigate seeing his family when his dad doesn’t know who I really am to his son? Should I try and spend time with them when I get off work even though it would be later in the evenings, around 11 p.m.?

A: I don’t know if your boyfriend is delaying telling his father because he’s worried his father might pull financial support for his college education, because he fears for his safety, or because he simply wants to avoid a difficult conversation. If you don’t have a clear understanding of your boyfriend’s fears, ask him. Does he plan on telling his father after he graduates? Over the phone after his father leaves town? Possibly never? It may help you figure out how you want to interact with his family if you have a stronger sense of your boyfriend’s plan.

When it comes to this particular visit, you have a lot of options, I think. If you’d rather not spend much time around them, since it means you’ll have to stay closeted, you can make your own plans with friends and see your boyfriend once they leave town. Or you might decide to join them for a single meal or outing so you don’t feel like a dirty little secret or like you’re putting on a show. Don’t force yourself to spend more time with them than feels comfortable for you, and if this starts to become a deal-breaker, be honest and upfront with your boyfriend about what you need.

Q. Lies: My husband died when my daughter was 3. He was violent, drug addicted, and abusive. My mother-in-law paints him as a saint. The man she describes to my daughter doesn’t exist and never did. She will straight up invent fictions on the fly. “Your Daddy bought you that teddy bear when you were born,” when in reality my co-worker gave it to me when my daughter turned 4. I have kept quiet until now because I depended on my mother-in-law to watch my daughter while I worked. I am finally starting to date again, and my mother-in-law is spoiling my daughter against any man I see. Daddy is always better, and why didn’t I love Daddy more?

I finally confronted my mother-in-law, and she told me that her son was the “best” I could do. I was insulting his memory. I asked her if she remembered driving me to the hospital when I was pregnant because her son hit me so hard I got a concussion and broke three fingers. That never happened, according to her. I have the medical reports. I couldn’t have finished my degree or worked without my mother-in-law helping me, and she adores my daughter. But I can’t help but resent her for holding me back in my life. My husband beat and abused me. I don’t know how to tell my daughter that, but I will not have her loving a fake memory. How do I deal with this? I don’t want to cut my mother-in-law out of my life, but she is sabotaging any hope I have of getting married again.

A: If keeping your mother-in-law in your life means listening to her tell your daughter that your abuser was a saint, and out-and-out gaslighting you by denying that the abuse ever happened and that you’re making it up, then I think you should cut her out. What she’s putting you through is absolutely unconscionable and is frankly cruel to your young daughter because it means that eventually when she hears the (age-appropriate) truth from you, she’s going to feel like she can’t trust the grandmother who’s been lying to her for years. Your mother-in-law enabled and facilitated your abuse when your husband was alive, and she’s now trying to sabotage your attempts to find someone new who treats you well—she’s not a safe or a loving person, and she doesn’t deserve to be a part of your or your daughter’s life.

Q. Re: Not so happy hour: This kind of behavior is why so many larger companies no longer allow alcohol at company events. It is the company lawyer’s nightmare, and the plaintiff lawyer’s dream. Many startups have not figured out that employment law applies to them, and they continue to do dumb things like encourage employees to get hammered together, regardless of what might ensue. That said, do not just put your head down and work! You should report this to either HR or your boss’ supervisor. Remember though, that they do not work for you and their loyalty is to the company. Sometimes, in the short run, people interpret that as meaning that they need to protect the company regardless of the cost to them or to the company in the long run. You may want to consult a lawyer before initiating anything in order to understand what other information you may need to collect. Regarding the drinking, stick to seltzer and start looking for a new job. It won’t get any better.

A: Yeah, this definitely doesn’t strike me as a situation where “Maybe things will get better.” I agree that mandatory company happy hours are a bad idea, although I think it’s important to point out that lots of people can have a few drinks and don’t suddenly bust out offensive, sexist terms to refer to their employees. Regardless, talking to a lawyer who specializes in workplace harassment will give you a stronger sense of what your options are. Thanks for this!

Daniel Mallory Ortberg: Thanks, everyone! See you next week.

If you missed Part 1 of this week’s chat, click here to read it.

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Classic Prudie

I’ve been married to a wonderful woman and mother of our three kids for 25 years. I’ve come to realize over the last five years that I don’t love my wife. I don’t hate her—she’s my best friend. But I have zero feelings for her. She’s put on 50 pounds over the last 10 years, which is a major turnoff. We haven’t had sex in five years due to this. I want to be happy, and I don’t want to hurt her feelings. I just feel like I’m on the treadmill of life going nowhere real fast. What to do?

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