Dear Prudence

Backup Plan

In a live chat, Prudie advises a woman who just found out her fiancé originally wanted to date her best friend.

Emily Yoffe.

Emily Yoffe

Photograph by Teresa Castracane.

Emily Yoffe, aka Dear Prudence, is on weekly to chat live with readers. An edited transcript of this week’s chat is below. (Sign up here to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Emily Yoffe: Good afternoon, everyone. I look forward to your questions.

Q. Boyfriend’s Old Emails Cause Drama: I met my fiancé at a house party. I was there with my best friend, who happens to be gorgeous. He began talking to us and kept talking to me after my best friend left. We made plans to hang out later, and over the next three months our friendship evolved into a wonderful relationship. Recently my fiancé and his good friend had a falling out, and in an act of spite his friend forwarded me a series of emails from around the time we first met. By reading them I learned that, initially, my fiancé only spent time with me because he wanted to have a shot with my best friend. He called me plain, repetitive, and mildly annoying. I know those aren’t harsh criticisms, and that they come from the first few days of our friendship. But I’m still upset, because those are my worst fears about myself, and it hurts to know that the person I’m marrying thought those things about me too. My fiancé couldn’t be more apologetic, and he’s been very sweet and reassuring to me since I received the emails. (He didn’t say those things out of hand, they were answers when his friend asked him about me.) I know he loves me so much. I still can’t put those emails out of my mind, though—what can I do to get back to being a happy bride-to-be?

A: The thing about love is that it’s a wonder drug that makes the initially plain, slightly annoying person into the most beautiful, fascinating woman in the world. There would be far fewer happy marriages if everyone who had an initial neutral or even negative reaction to their future spouse didn’t stick around to get to know each other better. I’ve mentioned their marriage before, but Paul and Julia Child were gloriously happy for decades. When they first met he thought she was a gawky, awkward virgin, and she thought he was a self-satisfied roué. But during the course of their friendship Cupid’s dart hit—just as it has for you. Your now-fiancé, after chatting you up, still could have pursued your friend. He didn’t. He probably now sees her as a really stunning woman who’s just not right for him, because you are. It also seems right that he’s had a falling out with his former friend, because what a jerk this guy is. Forwarding such emails in order to hurt an innocent person—well, good riddance. Humor can help here. Maybe when you find yourself nattering on about the wedding you can stop and say, “You know what, I’m finding myself to be repetitive and mildly annoying—although I do think I look pretty good.” It will be a relief for the two of you two laugh about how a great romance got its start.

Dear Prudence: 5-Year-Old Hitting the Bottle?

Q. Leave Mistress Daughter Out of My Will?: I was married for over three decades, and my husband was never faithful to me. I chose to stay with him for personal reasons, but I still think poorly of those who date and pursue married people. Since his death, I have invested the money my husband left me, and I’ve nurtured it into a small fortune. I planned to leave my three children a portion of my estate, donating the rest to various charities. But now my youngest daughter has moved in with a married man; he left his wife and his young children to be with her. I know from speaking with her that she feels no responsibility toward the destruction of his marriage; according to her, happy husbands don’t stray. I love my youngest daughter very much, but her actions anger and disappoint me. I no longer want to leave her anything when I die. I’ve told myself that children shouldn’t live in expectation that their parents will leave them money when they die. But I recognize that I might be blinded by bitterness towards my husband. What is the right thing to do?

A: Like father, like daughter. I wonder if she absorbed the lesson from her father that fidelity is for chumps. Since I think personalities are born and made, she and your husband may share the trait of not taking responsibility for their actions. I can understand your dislike for people who get involved with married people, but the transgressor in your marriage was your late husband. And whatever your reasons, you decided to put up with him, instead of end it, for 30 years. People have affairs and marriages do break up, but your daughter’s attitude is rather chilling. She is an adult, and you don’t want to and can’t dictate how she lives her life. But you can have a blunt conversation with her about how your father’s infidelity darkened yours and say to her it pains you to see her be a party to the end of a marriage. At the least, say that she must extend her sympathy to the children who are in terrible pain and who are going to be spending a lot of time in her home. Your money is just that—yours. You don’t say you expect to depart any time soon, so you don’t have to make a decision now about how to spread your wealth. Since you have enough for lawyer’s fees, you can also alter your will as often as you see fit. Your daughter’s new relationship might not last and she might reform. It might last and she might be a loving stepmother. Let this play out before you make your last will and testament.

Q. Confronted About Old Affair: A few days ago my new co-worker “Ralph” cornered me in the break room and told me he knew all about”the real me.” It turns out that Ralph is a good friend of “Cindy,” the woman I cheated on my wife with eight years ago. I thought I loved Cindy and told her so. I was a terrible human being at the time, and I was lucky my wife would have anything to do with me after she discovered the affair. I dedicated myself to saving our marriage and becoming a better person. Accordingly, I abruptly ended my relationship with Cindy and never looked back. I truly believe I am a different person than I was at the time I cheated. Ralph doesn’t think so, though. He obviously dislikes me, but we’re going to have to work together. I’m also worried Ralph will tell our co-workers what he thinks of me and why. How should I handle this situation? Cindy has apparently exaggerated aspects of our relationship, like how long we were together, and from what Ralph says she’s still fairly angry with me. That’s worrisome.

A: Your co-workers know you. And if you are transformed as you say, they know you as a decent man with a happy marriage. Suddenly, here arrives this new guy, who obviously has it in for you. If he explains why to everyone, “Didn’t you know that eight years ago Dennis cheated on his wife, then dumped the woman he was cheating with, even though he told her he loved her?” your colleagues will want him to put a sock in it. You need to calmly pull Ralph aside and say that your conversation with him was disturbing, but you don’t intend to discuss your personal life with him or anybody else at the office. Say you sincerely hope he can put his hostility aside because your workplace values cooperation. As for Cindy, sure she was hurt. But anyone having an affair with a married man has to be prepared to be unceremoniously dumped if her lover realizes he actually prefers his wife. If she hasn’t gotten any perspective on this in almost a decade, then she needs better friends than Ralph—friends who can tell her she sounds pathetic.

Q. Thanks From the Parents of “My Friend’s Dad Hugs Me Too Much”: Thank you for advising my teenage daughter to tell her mom and me about her friend’s touchy-feely dad when she wrote into you a few weeks ago. After several long discussions, my wife and I spoke to a police officer about our concerns. We were worried the police would scoff at our daughter’s experiences, because nothing strictly criminal occurred, but the officer took our concerns very seriously. We have since discovered that this man has been harassing another of his daughter’s friends; but instead of stopping at hugs, he sent her pictures of his genitals as well as sexually explicit emails. My wife and I could not be more grateful to you for giving our daughter the push she needed to confide in us.

A: Thank you so much for letting us know what happened, and I’m so glad your daughter got the courage to speak up. One’s heart has to break for the daughter of this fiend. I hope the community can reach out to this girl and support her—presumably her father is headed toward prosecution. And this just confirms that creeps taking advantage of minors should be reported to the authorities. It’s very likely, as in this case, that your kid is not the only one.

Q. Gun at Job: I just finished my first year of law school and have my first legal job. So far everything is difficult —but it should be, it is part of the learning curve. The other day I was doing some filing and I found a handgun in a drawer. I’ve never been exposed to guns before and I don’t know if it was loaded or not. I am scared of this gun because I use the filing cabinets all the time and I do not want to set it off unintentionally. Also, tempers run very high in this office and I am afraid that somebody who knows it is there might use it for dangerous purposes. I am lucky to have this job and I need it for the pay and experience. I am hesitant to bring this up to my job-placement office because my boss will absolutely know it was me who brought this up. I am hesitant to ask my boss directly because I do not want to appear weak or difficult. What is your advice?

A: You may have discovered that your boss has his own plans for reducing the glut of lawyers. I wonder what kind of law your firm handles—if it’s matrimonial or bankruptcy, let’s hope some sharpshooter at the firm doesn’t have to lunge for the drawer in order to subdue a dispute. Depending on where your firm is located, there may be laws regarding unsecured weapons. No matter where you are, a loose loaded one in a worksplace is alarming. I think you should take this to your school administrators. Explain this disturbing discovery, say you don’t know whether the weapon is loaded or not, and frankly given the volatility of the office, you are too uncomfortable to ask your boss about it. As hard hit as the legal profession is, your law school should be concerned that a student could be hit by a flying bullet. Let’s hope they find you another placement.

Q. Boyfriend’s Old Emails: I agree with you, Prudence. In high school I was the geek sophomore and youngest member of a choral group and got along with everybody in the group except one girl, a senior. We never hit it off. Next week we celebrate 36 years of marriage together. Unless she has evidence that her fiancé still feels this way, she needs to let that very small window of the past go and focus on her future with this guy who obviously learned that first impressions aren’t always the right ones!

A: Congratulations, and thanks for this wonderful story!

Q. Difficult Co-Worker: I’m part of a two-person department at work, and the other woman in this department is very difficult to work with. I’ve already spoken to HR about the main issue, which was how we divide up our work, and they have been supportive and pro-active in helping address this. I’d like your advice on how to handle a part of the problem that I’m not sure HR can help with. My co-worker is emotionally needy and sometimes makes me really uncomfortable. I think she would like us to be closer than we are. One time, out of nowhere, she told me she loved me. Sometimes she’ll talk in a babyish voice and say how pretty she thinks I am, or how “lovely” I am to work with, or how I have this quality that makes people feel good. She’s straight and married, so I don’t think she’s harboring some kind of secret crush, but I still don’t like this. She is also a nonstop talker, and I’ve gotten good at excusing myself from conversations, but there are still times she talks to me this way and I want to run for the door. Do you have any advice? Thank you.

A: Yes, human resources is supposed to help you when your disturbed co-worker declares her love and starts telling you look “so pwetty, just wike a widdle doll.” Go back and explain the problem has escalated beyond simply work division. Say your co-worker is making you deeply uncomfortable with her inappropriate behavior and personal declarations. If they don’t do anything but tell her to stop announcing her love, you may need to take this higher up in the company. Also start documenting her behavior. What you describe is intolerable. Given the unemployment rate, how is it that so many nuts retain their jobs?

Q. Bathroom Etiquette: Recently I went to a moving-in party for a friend-of-a-friend. When I got there I asked to use the bathroom. After using the toilet (for number two) I realized to my horror that the toilet would not flush. I stayed in there for 15 minutes trying to come up with any solution. There was no plunger or any tools I could use to better the situation because the house was just being moved into. I finally decided to go and tell my friend and ask her opinion, but not before the house owner tried to use the toilet. He was incredibly annoyed, and told me I had to “get it out of there!” which I promptly refused. All the rest of the night he made reference to the incident and the fact it was still in his bathroom. My question is, what else could I have done? What is the etiquette on such a supremely embarrassing situation? I don’t think he deserved money to compensate for my … mess, but is there anything I should have done? I still felt awful about the whole thing.

A: As a housewarming gift, find the volume of David Sedaris’ work (readers, which one?) in which he describes being in exactly the same situation at a friend’s house. In my recollection, Sedaris finally scooped the thing up and tossed it out the window. You were not obligated to handle the situation by defenestrating your number two.What happened was mortifying, but you dealt with it as best you could. It was your host who behaved like a turd. That his toilet broke is not your fault. If that was the only bathroom, he needed to put a sign on the door and wrap up the party early because of a plumbing failure.

Q. Re: Gun at Job: I think the writer could approach her boss, tell him/her about the gun, and say she’s concerned this poses a safety risk to anyone who might come across it. And if you found it, someone else could as well. Lawyers should be sensitive to potential liability. If the boss shrugs it off, then you talk to someone at school. Just be calm and professional about it. You’re doing the firm a favor pointing out this is a risk.

A: Good advice, thanks.

Q. Flaky Baby-Sitting Client: I am 20 and work as a baby-sitter to earn extra pocket money while I attend school. I baby-sit for a successful businesswoman and single mom. “Ms. H” has two daughters under the age of 7. I baby-sit for her two or three times a month, and she pays very well. Twice in the past two months she has stayed out WAY past when she told me she would be back—2 a.m. instead of 11 p.m., for example—and has not responded to my texts and calls. The first time she apologized profusely and gave me an extra $150 for my troubles; the same thing happened the second time she stayed out late, and when she came home her speech was slurred, I could smell alcohol on her breath. I felt uncomfortable leaving her alone with her kids but, when she rejected my request to spend the night, I left. I don’t know what to do now—stop baby-sitting for her? I’m worried about her behavior and how it could impact her kids.

A: As I’ve made clear in recent columns, I am a real prude when it comes to alcohol. What’s not clear from your letter is how long you have been baby-sitting. If it’s been a year of normal behavior, it could be that Ms. H has a new boyfriend and is losing track of time and her intake. But if it’s only been a few months, I can understand your concern that this is becoming a pattern. If you want to keep sitting, you need to have a talk with her. Yes, it will be hard, but standing up for yourself will be good training. Next time she calls tell her that you need to have clear hours you’re expected to sit. Say that you’ve got schoolwork and staying up until 2 a.m. isn’t good for you. If she says she understands, then continue to sit. And if she’s been driving herself home intoxicated, the next time you sit, before she goes out, pull her aside. Say this is difficult for you to say, but the last time she came home, you were concerned about her being on the road after having had too much to drink. Tell her you don’t want to worry about getting a call late at night that something bad has happened.

Q. Re: Busted Toilet: Or you do number two at your new mother-in-law’s house, the toilet overflows and floods the bathroom and hallway. That was 20 years ago and I’m still mortified.

A: But the decks were swabbed 20 years ago—surely this has become a funny story by now.

Q. Re: Gun in Office: My father was an attorney who at one point in his career defended a man who was accused of a pretty gruesome murder. During the course of that trial, he received repeated death threats (toward him and his family). From that point on, he kept a gun in his desk drawer and his nightstand. Attorneys receiving death threats is not uncommon, as you can imagine. Many older attorneys do keep firearms in their offices because they have received threats. As attorneys, though, they should be particularly aware of the risks associated with loose loaded firearms (and their potential liability for such). Speaking to your boss about your concerns will not make you seem weak, quite the contrary. Phrasing it in terms of liability for the firm will make you seem like a prudent future attorney.

A: Interesting, thanks. And another letter writer says it’s too late for another placement and talking respectfully to the boss is the way to go, which sounds right.

Q. My Parents’ Marriage Is a Lie: My parents have the most incredible marriage. My whole life I’ve looked up to them as a model example of a strong and happy relationship. Needless to say, they are loving and supportive parents as well. Dad is just as close to my half sister (who was from mom’s first marriage) as he is to me and people are amazed to hear we’re a blended family. Then I discovered something that changed my entire view of my parents. It turns out that when my mom and dad met, they were married to other people. The affair started when my sister was a baby, and continued for three years, until they each divorced their former spouses and married each other. What was equally shocking was that dad has a son from a previous marriage and he stopped seeing him altogether. I didn’t even know I had a half brother through dad. I always presumed people who have affairs or men who ditch their kids are scum, and it turns out my parents did exactly that. What’s worse, I found out accidentally (they didn’t have the guts to tell me), and when I went to them to see if there was some kind of justification—anything—well, there wasn’t any. They met, left their spouses and even a child, and married each other. Dad said he tried to see his son initially but “just lost touch with him” over the years. It makes no sense to me. I feel like our whole family is based on lies and betrayal. I feel sick and guilty that I had my father at the expense of my half brother. My parents apologized profusely for not telling me. How can I restore respect I once had for my parents?

A: It can remake your understanding of the world to discover the people you always thought were paragons are actually flawed—even profoundly flawed—people. Your parents ended up with the right partners—sometimes marriages cannot be saved—but at a high price. Even so, “losing touch” is simply not a justification for abandoning a child. You have found out what how your parents met, your parents have apologized for keeping it from you, but that’s not the end of the discussion. It’s the beginning. You don’t want your relationship with your parents to revolve around this, but you need to tell them you would appreciate it that now that this information is out, it’s no longer taboo. Explain there’s a lot you’re trying to process, and you could start with your half brother. Consider whether you want to reach out to him, and discuss with your parents and sister how to go about this. Talking this out, and the issues that have been raised, with a family counselor, could be a good way to begin this new phase of your family life.

Q. Re: Difficult co-worker: Thanks so much for taking my question. I will go back to HR. Your comment was very prescient: on Friday this co-worker actually did tell me I was as pretty as a doll. Yuck.

A: Amazing, and yes, yuck. Get HR on this case.

Q. Family Relationships: My husband’s brother, Bob, has been in a relationship with a woman, Sandy, for over 40 years. That’s not a typo: They are now in their late 50s and have “dated” off and (mostly) on ever since college, but never married. Sandy is a lovely person and I think of her as my sister-in-law. She attends family events and celebrates major holidays with us. Our daughters even call her Aunt Sandy. Recently, Bob was diagnosed with pancreatic cancer and the prognosis is not good. He asked my husband to help him get his affairs in order and to be executor of his will. My husband told me that except for his car and some furniture, Bob is leaving all his estate to our daughters to help with college expenses. I was shocked and assumed Sandy should get the bulk of Bob’s estate, given all that she has done and meant to him. Even now, she is taking care of him during his illness which would cost a fortune if he had to pay for such care. I realize Bob wants to leave a legacy, but we’ve been saving for our daughter’s educations, so the money, while a help, will not make the difference as to whether our girls attend college. But it would mean a lot to Sandy who is a retired schoolteacher with a small pension. I have encouraged my husband to discuss this with Bob and convince him that he should leave more to Sandy than a 1999 Jeep and a brown futon. My husband says that his job is to follow Bob’s wishes and he feels that talking about this with him is not appropriate. Everyone is pretty emotional about the diagnosis now, but I think this needs to be discussed soon. Am I off base?

A: Poor Bob, and poor Sandy. Of course as he’s facing death your husband wants to support his brother, not challenge him. But since Bob’s announced what he’s planning to do with his estate, he’s raised it as an issue, and it’s fair for your husband to discuss it with him. He can tell Bob how moved he is that Bob wants to help his nieces this way. But he can also reassure him that there are funds for their education. Then your husband can tell Bob all of you are concerned for Sandy. Your husband can explain that because you all love her, you hope Bob will consider leaving her a larger portion of his estate. Since any money to Sandy goes against your family’s interest, this will make a pretty compelling case.

Q. Confessions: I had the hardest time accepting that my boyfriend of eight years broke up with me. I begged him to take me back and was devastated when I discovered he started dating again within a couple of weeks. In my heartbroken and crazy state I lied and told him I was pregnant. He didn’t get back with me immediately as I hoped, but said he wanted to reconsider our relationship for the sake of the “baby.” Shortly afterward I realized how crazy I was. I told him I had a miscarriage because I was too embarrassed to tell him the truth. He is a good guy and he checked on me a few times after that to be sure I was okay. It’s been a few months since we last had contact but I feel awful about the lie I told. I don’t want him to go around for the rest of his life thinking he lost a child. I know I have to confess—but how? I feel so embarrassed and angry at myself for doing something so stupid.

A: Good for you for seeing that your devastation temporarily deranged you. Send him a brief note saying you owed him the truth, and that you’re sorry that in your pained state you mislead him.

Q. Re: Mistress Daughter: It also could be that the daughter is so uncomfortable talking about the specifics of her affair with her mother that she is minimizing any discussion with mom, and may feel entirely different than mom is presuming. The difference between daughter and father is that father apparently never left mom, while daughter is now in a relationship with a man who chose to separate from his wife. Now that the die is cast, what does mom want? She wants the daughter to behave in the way she wants, and she has no qualms about using her money as a weapon to make everyone toe the line. What she’s going to do is to drive a wedge between herself and her daughter and any children this daughter may have with her “unsuitable” partner, as well as between her daughter and her other children (presuming they also don’t “disappoint” mom). Remember that YOU raised her. She’s still your child.

A: Let me make clear that I hope mom is planning to keep quiet about her musings over her estate planning. I’m normally in favor of dividing estates equally—unless there are overwhelming reasons (a child with a disability, say) to do otherwise. Mom can eventually do what she likes with her estate, but I think she should not make any decisions about that now. And yes, working out her own anger at her husband on her daughter is very unpleasant.

Q. Puppy Problems: I’m hoping you can help my husband and me with a puppy problem. A few months ago my husband surprised me with our first puppy. George is a 6-month-old bichon-Maltese mix, and I honestly couldn’t ask for another dog as easy to train or as amazingly well-behaved. This is the first dog either of us has ever had so we aren’t sure how to deal with this current problem. George is left alone for about six hours twice a week. I just don’t feel right putting him a cage for that long and he’s a small enough dog (12 pounds) that our master bathroom has more than enough room for him to be comfortable and safe in. It’s appropriately puppy-proofed and he’s stocked with food, water, a puppy pad, and his favorite toys. It’s worked out very well until twice last week we came home to discover that he’d figured out how to turn the water on in the tub! I hate the idea of putting him in a kennel for six hours but I’m scared he’ll hurt himself if he doesn’t stop. Do you or your readers have any advice?

A: Your puppy wants to freshen himself with a bath before you come home, but he’s too young to be left alone for that long. See if there is doggie day care (which is different from a kennel) near you for those days you’re gone, or pay for a dog walker to take George out for attention and relief.

Emily Yoffe: Thanks, everyone. Talk to you next week.

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