Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at prudence@slate.com.)

Readers! Ask me your questions on the voicemail of the Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Q. My engagement ring diamond is too large!: Seriously, the diamond in my engagement ring is way too large! I know this sounds like a humblebrag or the rant of a crazy person, but it is true. My fiancé and I have been talking marriage for a couple of years, and he proposed over the holidays. I said yes of course. He didn’t have a ring and said he was going to surprise me with one. All good so far—honestly I love this guy to the moon and back so I was thrilled. Then two weeks ago he gave me the ring. It is huge, like something one of the Real Housewives would sport, and it is just not my thing. I am not a jewelry person at all. I hadn’t given much thought to a ring, but I thought something nice and tasteful would be great. This isn’t that. I told my fiancé how I felt and he kind of shut down. But finally he admitted that he thinks the diamond needs to be bigger than the one his brother gave to his fiancée. They are super competitive and always have been. Seriously, I do not want this ring, and I don’t want to be part of a war between brothers either. I found the receipt for the ring, and it cost more than a year of my fiancé’s salary! We can’t afford this! I don’t know what to do. This is making me rethink how my fiancé is, and I’m not liking what I see. Do you see any solutions here?

A: What an exciting opportunity to pursue healthy conflict you have been presented with! Your fiancé presumably wishes to marry you, not his brother and sister-in-law, therefore your opinion about the engagement ring is really the only one that counts. You don’t have to let yourself get encased in diamonds just to satisfy his weird, jewel-based rivalry with his brother. “The last time I tried to talk to you about my engagement ring, you shut down, but that’s not how I want us to handle conflict in our relationship. We need to be able to talk about these things, and it’s really worrying me that you seem more concerned with showing up your brother than what I want. I don’t like this ring. I’m not interested in lugging a giant rock around that doesn’t reflect my tastes and makes me feel self-conscious, and I want to feel like my preferences are important to you. I would like to return this ring and pick out a less expensive one together. I’d also like to talk about why you felt like you ‘needed’ to buy a bigger diamond than your brother did, and the fact that you were willing to spend an entire year’s salary on it. Can we do that?” Pay attention to your feelings! If you continue to not like what you see from your fiancé even after you have a follow-up conversation, consider giving the ring back altogether.

Q. Involuntary Peeping Tom: I live in a Southern state, and our home is located in a community of houses that are built pretty close together. Our neighborhood is a mix of families and young professionals. My husband and I have a 15-year-old son and an 11-year-old daughter. Our newish neighbor is an attractive woman in her early 30s. I don’t know her very well, but she seems perfectly nice. My issue involves the fact that she likes to lounge naked by the small pool in her yard. I found out that you can see her from our backyard deck when I caught my giggling son and his friend pointing her out. My husband and I spoke with my son about respecting someone’s privacy, that he shouldn’t make a spectacle of it, or God forbid take photos of her (I hoped to not have to say that to my kid, but in this digital age, it felt necessary to make clear). I brought it up to the neighbor in a “just so you know” way once, when I found out, and she kind of laughed and said she’d keep it in mind. But she continues to do it. And I know it’s her home, and she can lay/walk/dance naked on her property all she wants. And I don’t want to make the neighbor defensive about doing something totally legal. My husband and I aren’t even that bothered by it (although I’m sure my husband is bothered by it less), but I worry now about having people over and hanging out on the deck (like, “don’t worry—that’s just our naked neighbor, try not to peek, pass the wine”) or more importantly, I now worry if my kids have their friends over on the deck (do I have to tell their parents, like sorry, there might be a naked woman within your kid’s line of sight, but we’ll have snacks?). And if I do bring it up again, do you have any suggestions on what to say?

A: You’ve already mentioned it to your neighbor and she’s declined to stop lounging naked, so I don’t think there’s any reason to bring it up with her again, especially since, as you acknowledge, she’s free to do what she likes in her own yard. Your approach thus far seems fairly reasonable—generally you try not to look, and encourage everyone else in your family to do the same. If, however, you worry about making guests feel uncomfortable when they visit, consider putting up an awning or a series of deck umbrellas that block the view. It’s not as expensive as adding another six feet to your backyard fence, but it will spare you at least some of the worry that your next dinner party will be highlighted by unexpected nudity. (Expected nudity is fine.)

Q. He works hard for her money: My dear, sweet fiancé and I are both divorced, and in short, his divorce agreement sucks. I silently suspected this, but his lawyer confirmed it is “punishing.” For many ill-advised reasons, he signed it without counsel and four years later he’s using mediation to request some modifications to alimony (an uncapped percentage of his income for 10-plus years) and visitation (none stipulated). While their co-parenting relationship is very cordial, I’m skeptical his highly educated ex-wife will agree to jeopardize her status as a stay-at-home mother. If we married, I’m anticipating resentment at watching a growing 60 percent of his income—he’s likely to increase his income significantly in the next few years—go out the door. If nothing changes, can I distance myself from his painful finances with separate bank accounts? By remaining unmarried? Is this just a case of accepting someone with their (contractual) baggage? I don’t have kids, work, and am financially independent, so it’s not about the money for me. It wouldn’t be so hard if a chunk went to a college fund, or a trust for his kids. But, how can we start a life together and watch someone else live so comfortably off of his/our labor?

A: You can put off your marriage for another five or six years, if you’re not in a rush, or you and your fiancé could maintain separate finances after you get married. You could also get a prenup of your own together to protect your own assets and make sure that you don’t set yourself up for future financially unequal arrangements. The fact that your fiancé is currently attempting to amend his divorce agreement suggests that he’s making progress and becoming a better advocate for himself, both financially and personally. Talk to him (and a lawyer! and a couples counselor!) about what your goals are for your future partnership, what you’re afraid of, what you resent, and what you hope for as a couple. This is challenging but surmountable, I think, and you have multiple options before you, none of them perfect but all of them workable.

Q. Should I cut ties with broke friend?: My friend died 13 years ago, leaving his wife $1 million in life insurance. Since then, she has lived a high lifestyle. She bought two high-end cars, put in a spa that she keeps heated 24/7 “just in case” she feels like using it, remodeled her kitchen as a way to employ a boyfriend, and buys pot and booze for all her hanger-on friends. I’ve helped her over the years by doing her taxes, finding her a financial adviser, and keeping her home in good repair, all for free because I felt that this honored her late husband, who was my good friend. Well, she’s burned through the money, and is angry that the financial adviser can’t help her. She was warned years ago that this day was coming. I’ve tried to get her to live within her means, but she didn’t listen. She now needs to sell the cars and the house. I could help her navigate this, but I just want to walk away and let her end up homeless. Am I a bad person? Should I help her? I’m so angry. Her late husband looked out for her, even in death, and this feels like she’s spitting in his face.

A: You have helped her navigate this—you provided her with a financial adviser and have assisted her with her taxes for well over a decade. You are helping her by not intervening now. She is an adult who has had plenty of time to prepare for this day, and she has multiple options now; if she has numerous assets she could sell in order to finance her downsized lifestyle and is capable of finding a job; homelessness is not an immediate threat. Wish her the best and encourage her to take her financial adviser’s advice. That’s all the help you can, or should, offer her now.

Q. Coming out, take two?: I’m a trans guy in my early 20s. I’m out to my partner, friends, colleagues, professors … pretty much everyone except my own parents, who are conservative, religious, and unlikely to take it well. (I know this because I tried to tell them at a young age; they threatened conversion therapy if I didn’t shut up about it, so I did. I don’t know what they made of my profoundly unhappy teenage years and continued “androgynous” presentation, but I think they believe this really was a “phase.”) I’ve been approved for top surgery, and my friends have raised thousands of dollars to cover the costs, for which I’m enormously grateful—I haven’t reached the necessary amount yet, but I’m on my way. My question is: When do I need to talk to my parents? My partner worries that if I don’t give them the chance to contribute, they’ll be (or claim to be) even more betrayed, and that even if they aren’t interested in supporting me financially, they need to know about the surgery before it happens or their reaction will be far worse. I’m just scared that they’ll try to stop me (and frankly anticipate being disowned anyway). Is our relationship inherently worth fighting for because they raised me, even if the mistakes they made in the process left me suicidal? And if so, how do you come out to someone you know will hate you for it?

A: You do not need to invite your parents’ input before getting top surgery, much less give them the chance to contribute financially. Since you anticipate being disowned, it’s probably unlikely they’re going to turn a complete about-face and offer to help pay for it. You are not in any way obligated to disclose any medical procedures you undergo during transition. Getting surgery (especially surgery you have to pay for out-of-pocket) is stressful enough on its own. If you feel like this is a conversation you’d rather postpone, then postpone it until you feel prepared to do so. The important thing to bear in mind, I think, is that the conversation you want to eventually have with your parents is “I’m transgender,” not “I’m transgender, and I’m pursuing the following medical aspects of transitioning, and welcome your input.”

You cannot “betray” your parents by being transgender or getting top surgery; you are an adult and have the final (and only!) say over your own body. Given that the last conversation you had with your parents about being trans resulted in the threat of conversion therapy, it’s understandable that you would rather hold off on having a follow-up until after you’ve been able to recover from surgery. Tell your parents in your own time—or not at all. If you decide you do want to (re)tell them, keep it simple. “Mom, Dad, I told you I was transgender when I was young, and at the time you reacted so angrily I didn’t feel comfortable mentioning it to you again. I want to give you the opportunity to know me better now, if you’re willing. I’m still trans.” If they display any sort of willingness to listen without making threats, then maybe you can figure out a different sort of adult relationship; if their reaction is the same as it was the first time, you don’t owe them a relationship just because they raised you.

Q. Responsibility: When I was 18, I dated this boy. I was a really terrible girlfriend—emotionally manipulative, mean, and eventually kissed someone else. We broke up messily, tried again, I wasn’t worthy enough, I had a mental breakdown, and I don’t date anymore. Two weeks ago, I got a message from someone who dated him. Turns out, he finds girls who are sort of like me, and treats them the same way I treated him. Since this started with me and is essentially my fault what is my responsibility to these women? What should I do to apologize and mitigate their trauma?

A: Nothing. You are not responsible for how your ex treats the people he dates after you; none of us are responsible for how our exes behave in the world, and thank God for that. Take care of yourself and your own mental health. It sounds like you’ve been through a great deal over the last few years and should be focusing on your own well-being. It was presumably surprising to hear from a stranger who had also dated your ex and felt raw enough about it that she contacted you out of the blue, but you don’t owe her (or anyone else) anything other than basic respect and politeness. I’ll say it again because I think it bears repeating: Your ex-boyfriend’s behavior is not your responsibility. The fact that you were not a good girlfriend to him at 18 does not mean you have “doomed” him to recreate your past behavior. Whatever trauma (or mere unpleasantness) his future girlfriends may or may not have experienced, there’s nothing you can do to make them feel any better; they’ll have to do it for themselves and with the support of their own social circles.

Q. Re: Should I cut ties with broke friend?: You don’t need to help your friend anymore, but it might be useful to stop judging every little move she makes. Heating her spa 24/7 is hardly luxurious—we bought a house with a hot tub and whether we keep it heated or not barely makes a difference in our electric bill.

A: I have no idea how much it costs to heat a hot tub! Good to know.

Q. Who is Mother’s Day for?: I love my spouse and teen kids, but they treat me like a maid rather than a relative. I’ve tried various ways to get them to do their share, but they firmly believe housework is 100 percent on me. Like, they will literally drop trash in the middle of a floor when I am cleaning it and expect me to pick it up. Last year I said, “No Mother’s Day until you treat me with respect,” because getting a card doesn’t make up for being treated poorly the rest of the year and in fact kind of makes the contrast more painful. Spouse said, “I know you didn’t want a card, but I bought you one anyway.” Sigh. I just reiterated that this year, unless they change their ways, I do not want to celebrate Mother’s Day. Now they are all mad at me. Spouse isn’t speaking to me. Is Mother’s Day for me, the mother, in which case I can legitimately claim some say in what happens? Or am I obliged to let them pretend that a card and a box of candy make up for being treated poorly 364 days a year? I know they “love” me, in the sense that they are happy someone is around to clean up their shit, but just once I would relish being listened to.

A: I think you should stop cleaning up their shit. Your kids aren’t toddlers, they’re teenagers; in a few years they will be living independently and won’t be able to rely on the fact that their roommates love them unconditionally and are willing to do their laundry and dishes for them. I also think you should consider leaving your spouse, because they’re not willing to treat you with respect, and give you the silent treatment for complaining about being treated like a maid. I think, in fact, that you should quit your job as family maid, whether you decide to leave or not. Figure out what you would like to do that would make you happy, whether that’s taking up hiking or a team sport or going out with friends of your own who treat you like a human being and not Rosie from The Jetsons—something that doesn’t revolve around catering to your spouse and children’s every whim.

Mallory Ortberg: We’ve made it through another week, a little wiser, a little queerer. See you back here next Monday.

Discuss this column with Dear Prudence on her Facebook page!

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