Dear Prudence

Help! Everyone Loves My Sister’s Loser Boyfriend.

Read what Prudie had to say in Part 1 of this week’s live chat.

A woman at right stands with skeptical face, hand to chin. A young man is behind her at left.
Photo illustration by Slate. Photos by Deagreez//iStock/Getty Images Plus
and KCHANDE/iStock/Getty Images Plus.

Prudie is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat, which was guest-helmed by Nicole Cliffe. 

Nicole Cliffe: Hi, gang! It is I, your temporary Prudence, reminding you that it, like Shamu, is a title borne by those called to it. Let’s have a great live chat, OK?

Q. My sister’s loser boyfriend: My sister and her fiancé have been together for more than six years and everyone in my family adores him. I, on the other hand, am not so fond of him. He’s a mooch at best. For example, my family finds it endearing that he quit his job to follow my sister to her new job in a new city and that he works from home. (No one knows what his real job is.) I think that he lacks self-worth. My partner did the same as he did, but we picked a city where we both could have our dream jobs. My family also thinks it’s hilarious that he jokes about becoming a stay-at-home boyfriend, but I think that makes him a loser who lacks ambition (my sibling has multiple graduate degrees and she’s the first in our family with a doctorate). Every time he and my sister visit my parents, he stays all weekend, even though his parents live 20 minutes away and he has friends in the area. He’ll even stay at home with my parents if my sister makes plans with her own friends. My parents think it’s thoughtful that he’s always at family events, whereas my partner only visits for holidays. But I think it’s concerning that he doesn’t have a relationship with his family and also consider it a red flag that he won’t leave her side.

I haven’t seen my sister one-on-one in more than three years and I have had failed attempts at getting alone time with her. (He crashed our last girls’ trip.) I have given up on ever hanging out with my sister alone, but I still have to be around him during the holidays and family events. I have been very polite, but my patience is running thin. Should I say something to her, or do I need to accept the relationship and learn to be around him?

A: You need to accept the relationship and learn to be around him. There seems to be nothing particularly wrong with him, and it’s been six years. I think that you would feel differently if your brother had a girlfriend who quit her job to follow his, etc.

Q. The hand that fate dealt me: Sixteen-plus years ago, I met a man at a nightclub and we had an amazing connection. He was a young elementary school teacher and I was a college student. We danced the night away, and when the time came for us to exchange digits I thought it was romantic to tell him, “If it’s meant to be, we’ll meet again.” You see, in the early 2000s I was obsessed with the movie Serendipity. What girl wasn’t really? As time passed, I genuinely hoped I would run into him and definitely regretted that numbers were never exchanged. However, I eventually met the man who would become my husband and I figured that it was obviously not meant to be. I forgot about him.

Until this August, when the new school year started. It turns out that man is now the new assistant principal at my children’s school. The first time I saw him I couldn’t place him, but later that week it all came back to me. When we finally were face to face, there was a look of recognition, but I’m not sure he could place me either. I’m a happily married woman with children, and I assume he is too. However, the “if it’s meant to be, we’ll meet again” thing is really wearing on me. Do I just let this go? Do I ask him if he remembers me?

A: As a fellow early-2000s Serendipity obsessive, I urge you in the strongest possible terms to not blow up your happy marriage. The next time you see him, say, “David? I thought that was you!” Start a pleasant conversation, and do not start texting or having solo meals.

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Q. My sister-in-law’s Thanksgiving dinner: While making Thanksgiving plans this summer, my brother-in-law and his wife volunteered to host dinner at their home, which is out of state. As my sister-in-law had never prepared a holiday meal and is going to be seven months pregnant at Thanksgiving, I volunteered to assist and prepare a majority of the meal for the five people who would be attending. At the end of October, my sister-in-law announced that she had invited her family, bringing the total number of people attending to 11. She also invited people from work who may not have a place to go for Thanksgiving, which is of course very thoughtful of her. However, she has no idea how many of the people from work will actually show up, and she did not check with me to confirm I would be OK with preparing a much larger meal for 11-plus people.

Given that our flight has been booked since the summer and we are arriving the morning of Thanksgiving, I informed them that I was not able to cook for 11-plus people with only one oven (they live in a two-bedroom apartment) and such short preparation time. I explained that I would be happy to still contribute to the meal by preparing one large side dish, and I requested a specific side, as my mother-in-law has only said nice things about this specific dish (whereas she always finds something small to complain about regarding any other food I prepare—think along the lines of “this needs salt” or “this would be better with x ingredient”). I was told that this was fine until a week later, when I was requested to make something else because my sister-in-law’s brother wanted to prepare the same item.

At this point, I am annoyed at the whole situation and lack of communication. I feel like saying that while I am happy to attend Thanksgiving dinner, I will not be preparing anything. My husband completely agrees with me and said he will support me if I choose not to help. Part of me wants to sit back and quietly watch this circus unfold and avoid the stress of it all. Am I overreacting here? Should I agree to prepare something else, or would it be reasonable to just attend as a guest?

A: You are pissed off, and with good cause. Bring a large side dish and paste on a smile. You’re a good cook, or you wouldn’t have been overasked in the first place. Dignity is a dish brought back up beautifully to the correct temperature, served to ingrates.

Q. My friend borrowed $3,000 for her son’s tuition: A dear friend borrowed some money from me 18 months ago, nearly $3,000. While I don’t normally lend money to people, she, her husband, and their boys are like family. We’ve done holidays together and traveled together, and she may as well be an older sister. She called me in a bit of a panic saying she misjudged when tuition was due for college classes for her eldest son. (They have four boys.) While not rich, I am good with my finances and could afford to lend them the few thousand, especially since it was for education, and she has slowly paid me back over the past few years.

But here are the two issues: One, it just came to light that her husband didn’t know she borrowed the money from me. I was horrified; I assumed he knew. It turns out she was not on top of their finances and ended up going to her husband in tears and he helped her untangle their finances. But she has still not told him they owe me money and has asked me not to say anything to him. This makes me very uncomfortable because I feel like I’m deceiving him.

Second, they just took a family trip to Hawaii and did a lot of (expensive) activities while they were there. Good for them! Except they still owe me more than $1,500. I’m a little taken aback at her irresponsibility and that she thinks doing expensive extra activities on an annual vacation is OK when she still owes me for helping cover her son’s tuition.

Lesson learned. I won’t ever let her borrow money again! But I’m having a hard time with this whole situation, as I feel like a friend whom I love and trusted took advantage of me. And what’s more, I feel complicit in the deception she’s running with her husband.

For what it’s worth, aside from this scenario, she is a generous, caring, kind person, and I really do love their family. What’s thrown me for a loop is that this behavior is outside the normal from what I know of her. That said, is there anything I could have done to help my friend and also avoid the messy situation I’m in now?

A: Look, the past is the past. You know you’re not going to lend her money again. Has she behaved inappropriately? Yes. Did she write me to ask? No. I would not worry about being duplicitous toward the husband. They are two separate organisms, and it’s $3K and not $10K, and it needed to be paid then. And you have almost half of it back already. Call and say you were a little surprised to see they took an expensive vacation while still owing you money, and ask for a firmer payment plan.

Q. Re: My sister’s loser boyfriend: This sounds like the letter writer is projecting a lot of pain about missing her sister on her sister’s boyfriend. It could be that your sister has no idea that you want to spend one-on-one time with her. Tell her how you feel, honestly, without including the boyfriend in the discussion. Just say that it would mean a lot to you if you could count on some one-on-one time with her here and there, without her boyfriend, and leave it at that.

A: This is great advice. It’s hard to take serious offense at “I’d like to just do sister stuff sometimes.” And use some of that time to ask your sister what she loves about her boyfriend, and listen to her.

Q. How do I explain to my child that I’m adopted? My parents divorced when I was 6 and my birth father kind of dropped off the radar. I still had some contact with my paternal grandmother, but by and large that whole half of my family disappeared. Not long after the divorce, my mom met another man who ended up adopting both me and my sister, and then he and my mom had two more children. Now, this is my family as I understand it: He is and has been my dad since I was 12 and my brothers are just that, little brothers (not half). I have a 2-year-old now and I’m thinking ahead to when this may come up. I still have some childhood books with my former last name on them; this is how my brothers found out the story. I expect that my daughter will find this out eventually and I have no idea how to explain. My husband has told me he will fully support however I decide to go about it, but I’m at a loss.

A: Get a book about adoption aimed at small kids, wait a couple of years, and then just tell her that you, yourself, were adopted, while reading it. I do not think your daughter will have any intense emotional reaction, as long as you don’t mirror one to her.

Q. Spent my entire paycheck in one day: I got my first paycheck from my new job yesterday and … I went a little crazy. Long story short, I got four haircuts from four separate barbers. I don’t know why I did it—I wanted to treat myself but I think I went a little too far. The first haircut was not a lot of money, $25 including the tip. I was in a good mood so I went to another highly rated barber and got another haircut, and then another, and then another. It added up quickly, and now I have spent my entire paycheck in one day and my hair is as short as it can be without being bald. I’m fine with the money I have now, I’ll be able to make it to my next paycheck, but I feel depressed and empty knowing that all of the money that I worked so hard for went to waste on four haircuts. It hurts even more knowing that I could have just gotten an extra-short haircut the first time and not paid for the other three haircuts. Also, I didn’t even use one of the haircuts to shave my facial hair, so I almost went to a fifth barber for the shave before I realized that I had spent my entire paycheck. How can I cheer myself up after this and how can I better budget myself in the future?

A: This is … bizarre. This is bizarre behavior. I know you’re not thrilled about it either, so I do not want to scold, but it’s important to register how absolutely wild this was. I suggest you cheer yourself up by making a budget for your next paycheck (and future paychecks). People love YNAB. If this, or any variation of this (buying 100 watermelons) happens again, get thee to a therapist.

Q. Co-workers trying to chip away at my one work perk: I recently started a new job at 75 percent my prior pay. I took this pay cut because this job is task-based and allows me to come and go as needed. One of my co-workers was turned down for this position. She knows about the pay. She continues to promote the idea that I should be here from 8–5 every day. She makes subtle underhanded comments about my work ethic and schedule. Slowly some of the other people in our office have started to follow suit. Our work is entirely unrelated. We do not share workload. So far I have tried showing her genuine kindness, helping out with her tasks, politely addressing any issues she tried to raise about my position. This hasn’t had any positive effect. Now, I’m just saddled with extra tasks that go unappreciated by her. She has no official power over me, but I have seen where this goes. I don’t want my one big perk to be reconsidered because a jealous co-worker ruined my reputation. My boss is in another state. Her role is only monitoring my quality of work and output, but news has traveled in this company before.

A: There is a lovely French phrase (“faites attention à vos propres oignons”) that roughly translates to “mind your own onions/business.” This co-worker could learn a lot from that.

It sounds to me that saying, “Jane, I think you misunderstand my arrangement with my boss,” then briefly explaining it is something you have already tried. If not, do that. Repeat if someone else says something. It is indeed no one else’s business, but it’s definitely impacting your work, or soon will.

If this escalates, email your boss and say that you love your current arrangement but you think many of your colleagues think you’re a slacker for not working 8–5. Here’s the key: Ask her for advice, after saying you’ve been ignoring it for several months. She may say something to the team, but it plays better than “can you tell them to lay off me?”

Q. Re: My friend borrowed $3,000 for her son’s tuition: If you loan anyone money without getting a signed promissory note—that you plan to collect on!—it is not a loan. It is a gift.

Be glad you have half of the loan back. I bet that puts you in at least the top 20 percent of givers/loaners.

I don’t think I would say anything to your friend. Then you might lose good friends as well as the money.

A: I think she’s sufficiently steamed that she’s going to say something to the friend regardless, but your first point is so good. I do not “lend” money—I give money and do not expect to see it again. If you can’t afford to give the money, don’t assume a handshake loan will result in you being made whole, and Just Say No.

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Classic Prudie

Q. Should I have a baby using my dead husband’s sperm? I met and married my husband when I was 21 years old and he was 41. Our marriage has been ridiculously wonderful for five years. Then my husband died unexpectedly. It has been almost a year since he passed. I am still close with my late husband’s mother, and because he was an only child who had no children, I know one of her griefs is that she will never have grandchildren. What almost no one but me knows is that before he died, my husband decided to deposit some sperm at a local fertility clinic. We wanted to wait to have children, but he was concerned about how the quality of his sperm would decline as he aged. The sperm is now mine to do with as I will, and I am only now getting around to deciding what to do with it. Though I am financially equipped to be a mother, I do not want to artificially inseminate myself. I do not know if I could handle raising our child without him. I also believe I will be ready to date again in another year, though I hate myself for feeling this way. I feel horrible for caring more about my future than continuing my husband’s family. And I know my mother-in-law would thrive as a grandmother. Can you offer me any advice, please?