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 voice mail 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. Engagement ring all wrong: I got engaged recently, and while I’m so happy to be marrying a wonderful man, there’s one little problem: I hate and am embarrassed by the ring he bought me. The diamond is so big, and the setting so flashy, it’s completely unlike the kind of rings most of my friends got. The problem is when he proposed and offered me the ring, my initial reaction was overwhelmingly positive. I gasped and gushed about how beautiful it was, and on the surface it is a beautiful ring—just not right for me. I’ve gotten so much unwanted attention, with people asking to see “the rock” and calling me celebrity nicknames. My mom has used every synonym for tacky in the book, and friends have asked if I know whether or not it’s a blood diamond. It’s humiliating.

My fiancé is so proud that he was able to get me such a nice ring since he comes from a working-class background. I just don’t know how to tell him that I want him to take it back and get a semi-precious stone or something more to my taste. I already tried telling him that it was too much money, but he has a great job and got a really good price, so he can afford it. I’d do anything rather than hurt him, but I’m supposed to wear this ring for the rest of my life. What do I do?

A: Good news: You get to have an embarrassing conversation with your fiancé! There is no way out of this, especially if you plan on spending the rest of your life together, which will almost certainly entail having at least four or five more embarrassing conversations before one of you dies. The longer you wait to have this conversation, the likelier it is that you will accidentally lose the ring or betray your true feelings about it to someone else in a way that gets back to him.

Be direct, and get it over with. Tell him that you’re embarrassed you didn’t tell him sooner but that you were so bowled over in the moment, so excited to be getting married, that you didn’t have room for anything but joy. Tell him it means so much to you that he wanted to make such a grand gesture by buying you a big engagement ring, but that it’s simply not to your taste, and you want to pick out a replacement together. If he’s deflated or embarrassed, listen to him. I’m sure he would have liked to get it right on the first try, but presumably what he really wants is to get you a ring that you’re happy wearing, not for you to feel guilty and uncomfortable whenever you look at your left hand.

Q. Was I used?: I dated a man who owns his own professional firm for over a year. A year ago, I quit a waitress job to study for a board licensing exam. I scraped by doing rideshare work to pay my bills, and he disliked it because it wasn’t “sexy.” (He even let it slip that I should be a stripper.) He traveled for the holidays and his firm fell apart—one employee had a job offer elsewhere and one was always away from the desk, then quit without notice. He asked me to temporarily fill in and I agreed with the condition that he hire someone else permanently. When he returned he said, “I think we should go on break until this project is over; for ethical reasons.” I reversed his business’ decline and boosted revenue so much he had to stop taking in clients. One of his tenants wanted to break their lease, so I had to find a new tenant for him. It took four months for us to find him a new employee. (Guess who had to receive and screen the résumés.) I told him over text that I was hurt that he dumped me for helping him.

He said that he didn’t consider a break a breakup, that he didn’t anticipate this would take more than a month, and that I was paid and needed something on my résumé, so don’t feel bad or regret. After training the new hire, I revisited the subject again and told him he broke my heart. He said that I shouldn’t be upset, that it was a difficult time, that he considers this an even exchange, that he could’ve used a temp firm instead of me, and I could’ve gone to work at McDonald’s. At this point, I can’t convince him of my point of view, and he swears he calculated the situation to work out for both of us.

Since the new hire, I’ve declined any new “projects” for his firm because that’s extending the break, and to me, an indefinite break is a breakup. I don’t want to work for someone who dumped me. We’re still in touch and he considers us back together. Although he was a very nice and caring guy before this episode, I’m not sure if I can move past this. He thanked me many times during the period he made me miserable, yet I feel used.

Am I missing something? Should I just cough it up to a difficult time? I need perspective. I ran out of savings and secretly did rideshare to get by. I’m expecting a verbal fight real soon where I’d retort, “I had a sexy job. You dumped me.”

A: I lost patience with this dude less than halfway through this letter. I have absolutely no idea why you would even consider speaking to this guy again, much less go out with him or help him out professionally. As a boss he was a jerk. As a boyfriend he was manipulative, selfish, and cruel. You told him he hurt you and his response was, “Go get a job at McDonald’s.” (That’s not a knock against working in fast food, by the way, but the fact that he thought that was a relevant response to your honest confession about your feelings speaks volumes.) The fact that he “considers [you] back together” even though you don’t want to work with him and don’t like the way he treats you says a lot about his character.

My perspective is this: Lose his number, ignore any and all future attempts on his part to get in contact, whether it be via sext or LinkedIn request, and practice saying “No” to people when they make unreasonable, unkind demands on your time and energy in the future.

Q. Jealous: “Kay” and I have been friends for over 12 years; we dated briefly in high school and stayed in touch through college, marriage (hers), moving (me), and divorce (hers).

I have been dating “Nina” for about a year and it is getting very serious. We are talking about getting a place together. Kay and her son, “Nick,” live near my brother and my parents. They come over to cookouts and my sister-in-law regularly trades babysitting with Kay. Every summer, my dad, brother, and I go out to the woods for a fishing and hunting trip. Since Kay’s ex is a waste of space, we’ve brought Nick along for the past three years. It was stupid on my part, but I never told Nina that I dated Kay. It happened so long ago, I honestly forgot. Last time we visited, my mom brought out the old photos and there was one of Kay and I at our junior prom. It upset Nina and she wanted to know why I lied to her about Kay. We argued and I thought it got resolved until we got back. I caught Nina going through my text messages to Kay, and she told me that my relationship with Kay made her “nervous.”

Now Nina wants me skip my fishing trip to go to some wedding with her for a cousin who lives out of state. She was planning on going with her sisters, but now she insists I go. I don’t know what to do. I promised Nick I would come and I hate to disappoint him, plus I hate weddings and have never even met this cousin of Nina’s. But I do love Nina. Kay is always going to be in our lives if only because she and my sister in-law are joined at the hip. The entire situation is so ludicrous, half the time I think it is all in my head.

Can you help?

A: I think there are two important issues here! One is that it’s not completely ludicrous for your girlfriend to feel unsettled that you never mentioned you dated Kay; the other is that it’s also reasonable for you to go on your annual trip and to make it clear that Kay and her son are an important part of your (and your family’s) life.

You can, and should, apologize for not mentioning that you and Kay dated, but you should also stress that this was over a decade ago, when you were a teenager, and that Kay is a dear family friend whose son is like a nephew to you. Kay’s not a serious ex from your adult dating life—your romantic relationship never made it out of high school. If Nina merely needs to be reassured that you were not actively trying to mislead her and that there’s nothing going on between you and Kay, then I think you can do that easily enough.

If, however, what Nina wants is for you to drop your friendship with Kay and her son because she’s jealous, then I think that’s an unreasonable expectation and not one you need to honor. You’ve already committed to your fishing trip, and more importantly, you value the time you get to spend with Nick. So I think you should go. There are other ways to demonstrate your commitment to Nina. It’s one thing for Nina to ask for reassurance and be honest if she’s feeling jealous or insecure, but it’s not OK for her to go through your phone or ask you to ditch a young boy who looks up to you.

Q. Ghost boyfriend: I’ve been with my boyfriend for two years and he’s creative, interesting, and sensitive. The only problem in our relationship is the way he resolves and reacts to conflict. He’s in no way abusive or aggressive, but he’s very sensitive and when he gets ticked off with me, he just ghosts me. I don’t even find out that there’s a problem until I realize he hasn’t responded to my last few texts. My heart sinks when I call and receive no answer. Then comes the anxiety of trying to figure out what I did wrong and getting him to talk to me about it.

It’s often over things that I don’t consider to be worthy of the panic this ghosting induces in me. (Recent examples: I forgot his mother’s birthday; I didn’t text him to let him know I got home safely; I fell asleep during his favorite movie; he caught me smoking a cigarette when I was supposed to be quitting.) When I finally out he was mad about me not remembering his mom’s birthday (from his friend), I was literally shaking, called her and apologized, and sent a belated gift—only to discover she was in no way fazed. It still wasn’t good enough until I apologized to him in person. Then everything was perfect again. But I know it’s only perfect until I screw up again, and if I’m ever mad at him, he just acts like I’m being crazy.

I’ve invested two years in this and right now, things are going really well. But I don’t know if I want to wait for it all to get passive-aggressive again. Should I break up with him now and make a clean break when things are good? Or should I try couples counseling?

A: Breaking up or going to couples counseling are both good options! This avoidant strategy of his would drive me absolutely up the wall, but if you believe he’s interested in trying to change, then by all means give couples counseling a try, and ask him to make a good-faith effort at finding a better way to tell you when he’s upset. If nothing’s changed after a few months, you still have the option of ending the relationship.

You know him better than I do, of course, but the fact that you don’t say whether he wants to change, plus the fact that he treats you like you’re “crazy” when you get upset with him, suggests that he’s pretty happy with things the way they are. That’s not a great sign for how much couples counseling might help the two of you. If you’re worried you don’t have sufficient cause to break up right now, let me assure you: You definitely do.

Q. Re: Was I used?: Mallory, you are completely off in your reply on this one. The stripper comment is a red herring and unrelated to everything pertinent.

The man did nothing wrong; when crisis hit his office, he ASKED her to step in, paid her for her work, and made clear at the outset that the relationship was going on hold. There was no lying, manipulation, or anything of the sort.

If she didn’t like his terms, if she thought it was benefiting him more than her, she had all the opportunity to walk away. She chose not to. She now needs to live with the consequences of her decision.

A: What do you think “living with the consequences of her decision” ought to be? She’s not trying to sue him for back wages or destroy his business. She just doesn’t want to date or work for him anymore. He asked his girlfriend to step in as an office manager, dumped her while she held the job to “avoid an ethical conflict,” then insisted she get back together with him once his business had been saved. She doesn’t want to. Are you suggesting that she is obligated to continue to date him because that’s the “consequence” of her decision? Because, you know, if so, all I have to say is: Bosh and flimshaw.

Q: Uneven salaries: One of a group of friends is a talented programmer earning a large salary while most of our group is still starting out or living off student loans. The problem is this: He has started to give large, unexpected gifts.

Some members of the group take free and full advantage of this, but others are uncomfortable or complain he’s showing off. He thinks I’m ridiculous to refuse $200+ meals and expensive gifts. He makes expensive plans and refuses to consider cheaper suggestions when I tell him I can’t afford to go. He just says he’ll pay for everyone.

What do I do? I’m uncomfortable accepting these gifts, I feel like I’m taking advantage of his good fortune, but I’m struggling to explain to him again and again that I don’t want or need him to buy me things; I’m happy to live within my limited means. We’ve been friends a long time and I care about him—I’m worried about other people taking advantage of him as well as the impact this constant fight is having on our friendship. How do I explain this to him? Am I being ridiculous? Help.

A: It’s perfectly appropriate for you to decline his offers if they make you uncomfortable, but I think it’s a step too far to tell him he’s being taken advantage of by his other friends. If he wants to treat them to expensive dinners or the occasional bauble, then that’s his prerogative. You might find it in poor taste, or a sign that he thinks he needs to buy people’s friendships, but he’s not being tricked or manipulated into anything he’s doing. Tell him you’d rather get together sometime for a walk or a home-cooked meal than an expensive night out, but don’t try to tell him he shouldn’t treat other friends who are comfortable being the occasional recipients of his largesse.

Q. No ocean for him, an update: A couple of weeks ago I wrote in asking advice on how to deal with my brother and SIL hounding my 5-year-old nephew about going in the ocean. I asked that we not give any of the kids a hard time about not going into the ocean. It turned out that my nephew had already said he would not go in the water at all again this year but he would play in the sand and swim in the pool. Thankfully, my brother and SIL respected his wishes. No threats of ending the trip early, no dragging the boy to the water. The entire week was much more relaxing for everyone.

A: This is the most reassuring update I’ve ever gotten from a reader. Thank you so much for letting us know your brother and his wife have seen reason!

Q. Re: Re: Was I used?: Prudie isn’t wrong.

You write: There was no lying, manipulation, or anything of the sort. It’s worse than him being inflexible and incredibly dismissive several times—“become a stripper” or “go work at McDonalds.” He tells her she should be grateful—he could have used a temp. According to her, she turned around the company and took on many more roles than in her job description. He’s trying to manipulate her because he’s onto a good thing.

A: That’s a key point, I think! He acts as if he did her a favor by offering her a job, when in fact she was doing him multiple favors by acting as his co-landlord, hiring manager, new employee trainer, and office/project manager. (One of the details we had to leave out for length, by the way, is that she often worked off-the-record overtime because she was given more work than pay. This was not a quid pro quo situation!)

Q. Closeted at work: I’m a young lesbian female working at a small nonprofit. I’m still fairly closeted at work. Last week a co-worker, “Beth,” shared her thoughts on gay marriage with another co-worker. Her remarks were benign at first, but then veered into the territory of thinly veiled homophobia. Here’s the catch: The co-worker who heard these remarks is not only one of my closest friends but also a closeted lesbian herself. She, of course, gave me a heads-up about Beth’s diatribe.

Beth and I work in the same small physical area and interact for at least several hours per day. Until this incident, we’d had a fairly warm working relationship, sharing details about our lives and eating lunch together at least once a week. I now find it difficult to authentically engage with her knowing how she feels about people like me.

Do I a) ignore it all, and continue inauthentically interacting with Beth; b) try and “bait” her into sharing these opinions to me directly so I can engage; or c) report the remarks to HR? Is there another option I can consider?

A: I think inauthentic interaction is the safest way to go here. Trying to bait a co-worker into expressing homophobic sentiments is not a good use of your time. If Beth volunteers an anti-LGBT opinion, you can of course firmly disagree and ask her to cut it out. You can even go to HR if she doesn’t let up. But don’t try to get her to talk about gay marriage at work again. Be polite, be professional, and feel free to have lunch with somebody else.

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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