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.)

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Mallory Ortberg: LET’S DO THIS!

Q. Why should I?: My on again/off again boyfriend of 15 years wants me to leave my husband and be with him. But he refuses to divorce his wife even though they are $50,000 in debt because of her. He refuses to help her until she helps herself. Now he’s allowing his children to make the same spending mistakes by letting his oldest go into debt for college out of state instead of making a better financial decision with an in-state college. I told him why should I leave my husband who provides for me and isn’t in debt for a person who complains about his wife all the time but never does anything about it?

A: This letter provides an exciting challenge, because I don’t believe I have an ounce of sympathy for either of you, and I’m finding it particularly difficult to wish for good things for your future. Such opportunities come rarely! It sounds like you do not wish to leave your husband for a financially insecure married man, and I suppose you have your answer there. I can’t imagine what sort of life you three would have together, if you left your partner but he stayed with his. As a longtime mistress, you have very little say in where your boyfriend’s children go to school, no matter how sound your reasoning. Something tells me they would not appreciate your financial advice. Stick with the bed you’ve made for yourself.

Q. Commemorative tattoo: My dad passed away just under two years ago. We were extremely close, and it was very unexpected. In a lot of ways I’m still reeling. Since before his passing, I’d always thought I’d like to get a tattoo somewhere down the line (I’m only 22) but was never sure what of. But since then, I’ve been thinking about getting a tattoo in my dad’s handwriting of a sweet message from a card he’d written me, maybe eventually adding a watercolor image from a beloved children’s book we read together countless times. The problem is, my dad was never a big fan of tattoos. If I’d gotten one when he was still here, I know he wouldn’t have held it against me, but he might not have been happy. A part of me feels like getting a commemorative tattoo for him would be disrespectful since I know he didn’t like them. Another part just wants to get the tattoo. What do you think?

A: I can’t think of anything more charmingly appropriate than commemorating your father in a way that would have made him feel both moved and mildly disapproving.

Q. Strange interview: I had an interview this week with a very small, local dentist office. I was called for an interview for an office-manager type job. The man who interviewed me, who is also the dentist, was probably around 80 years old and was asking me very uncomfortable questions. He asked if I was married, did I have kids, what church I go to, do I have anything wrong with me physically, and a lot more deeply personal questions. I am obviously not taking this job because it would be a horrible fit, but I’m a little worried about him. If he interviewed someone and they aren’t as easygoing as me, he could get in trouble for asking these questions, right? He does have a receptionist, should I call her and give her a head’s up about the kinds of things he was asking me and suggest that he needs to knock it off? I don’t think there was any malicious intent, I just think he might be unaware how dangerous it is to ask these kinds of things. Any advice would be great!

A: Technically speaking, it’s not illegal to ask these questions during a job interview, although it is illegal to base hiring decisions off of their answers, which is why most good employers don’t ask them—no point. Based on this dentist’s age and the general read you got from your conversation, it sounds more like he was trying to make conversation and didn’t realize he was asking inappropriate, intrusive questions that he could not use in his decision to hire a candidate. That doesn’t make it all right—there are very good reasons not to ask those questions—and you’d be perfectly justified in making a phone call, if you wanted to follow up with his receptionist and take yourself out of the running for the job, letting her know that at least part of the reason why is the series of personal questions you were asked unrelated to your ability to do your job.

Q. Not a restaurant: I am a stay-at-home mom with a toddler and a middle-schooler and take care of my nieces, nephews, and neighborhood children. Most of us can’t afford the ridiculous rates that child care costs in our area. I am lucky that my husband’s salary is enough for us to live on—I vividly remember when it wasn’t. My problem is that I have five to seven different children plus my toddler running around my house at any given time. I can’t indulge tantrums—my nephew is 5 and turns into a tiny tyrant when food is involved. He doesn’t like yellow, the carrots and peas are touching, etc. He is my sister-in-law’s only child and I know she feels great guilt for her long hours, but I can’t and won’t throw away good food and remake a meal based on whims. If you don’t eat the meal in front of you, you don’t get anything else. Missing dinner or a snack now and then will not harm him, but this has become a great source of conflict between us. I don’t ask for money beyond groceries and gas but I am this close to telling her to look for other after-school care. I grew up dirt poor and my grandmother could barely feed us some days. I am not going to impart the self-destructive and self-absorbed values where children are given everything so they appreciate nothing. I need an outside opinion before I pull the trigger and cause a rift in my family. My husband is away but supports me. My mother-in-law wants peace between us.

A: You sound like a woman who reached the end of her rope about 15 ruined meals ago. I hope you don’t feel that you are personally responsible for defraying the costs of child care in your city. It sounds like you’re stressed to the point that a little child’s fussy eating habits are striking you as an example of everything that’s wrong with his generation. That’s not a healthy way for a caretaker to view a child, and this isn’t good for any of you. That’s not to say you’re wrong to set limits, or to offer him the option of eating the meals you’ve prepared or waiting to eat until he gets home, but surely you must realize that a little boy who has tantrums about food combinations is not the same thing as “appreciating nothing,” and that he is not trying to malign your grandmother’s sacrifice. This situation is obviously untenable, and the best thing you can do is be honest about what you are and aren’t willing to do so that your sister-in-law came make alternate arrangements, since neither of you are getting what you want in this state of affairs. Give her, and the other parents, a reasonable deadline of a few weeks or so—don’t insist they all take over tomorrow—but you’ve been running a free day care for long enough, and it’s time for you to retire.

Q. OK to stay home?: My stepbrother is getting married in two weeks, and my husband and I originally replied that we’d be going to the wedding and made our travel arrangements. We were looking forward to both the wedding and spending the weekend with my family (we’d all be staying in a house together for the weekend). We’ve also been struggling to start our family for about five years. We’ve gone through a miscarriage, multiple IVF failures, and about a month ago we were matched with a pre-adoptive placement through foster care. We were elated about the placement, but the timeline conflicted with the wedding and we couldn’t take the children out of state so we backed out of the wedding. Except, we never canceled our tickets and now the placement has fallen through (and two days after it fell through my brother’s wife had another baby). We are devastated about yet another loss and, while we could technically make it to the wedding, spending a weekend with my family and their children (and especially a brand new baby) feels exhausting. Yet I’m also torn because we could technically make it because we didn’t cancel our tickets. Can I take a pass at this one or should I suck it up and just go? For what it’s worth my husband now wants to stay home, but I’m torn.

A: You’ve already told your stepbrother that you can’t attend, so it isn’t as if he’s going to be expecting you—take the pass and take care of yourselves. You’ve suffered a real and a grievous loss, and you won’t be any good to your family if you tried to go while you were still in the first moments of grief and shock. Take your brother and his new partner out for dinner to celebrate their wedding when they get back, but you don’t have to force yourself to attend a party when you can barely get out of bed just because you don’t want to “waste” the cost of airfare.

Q. Conflicted and heartbroken: My boyfriend and I just celebrated our third anniversary. We bought a home recently after nearly two years of living in an apartment, and want to get married someday. I have one child from a previous relationship, who adores him, and he treats him as his own. He’s been great in his fatherly role. I have been upfront with my boyfriend about certain things I will not tolerate (dishonesty and cheating are the big deal-breakers. My child’s father cheated on me, and I eventually left him). Our relationship is strong, and we are happy. I found out recently that just before our first anniversary, he went to an ex-girlfriend’s house after he spent some time at a bar that he goes to occasionally. This was previous to our living together, but we were exclusive. I assume he was there either late, or spent the night. I don’t have details on that. I just know that he bought beer and went to her apartment. I can only assume something happened, especially since he never mentioned going to a friend’s house afterward (he usually does). I’m crushed. I never knew this information before, and had I known at the time, we would not be where we are today. I am heartbroken, disappointed, and feel less confident. It wasn’t like we were together for a few weeks—it was almost a year. I feel he not only hurt me, but by extension, he did a disservice to my child as well. They are not friends on social media. Since two years have passed, should I say anything? Do I keep this secret to myself? What can I do?

A: If you have the opportunity to trade vagueness for clarity, back channels for direct conversation, and uncertainty for honest self-disclosure, I can’t imagine why you wouldn’t say something to your boyfriend. Based on your letter, it sounds like you found out this information from a possibly misinformed third party; who better than your boyfriend to fill in the details of what actually happened? You trust him, he’s given you no cause to doubt his word, and your relationship is otherwise good, so speak up. Don’t lob accusations or fill in the blanks for yourself, but tell him that you’ve recently learned something that makes you uncertain and anxious, and you’d like him to tell you what happened that night. Then listen. It may be he admits to something you find unacceptable; it may be that he has a perfectly legitimate explanation; it may be that you two have to fight about this, or break up, or laugh off a misunderstanding. But give him the chance to shed light on what is now just a rumor.

As an aside: I understand the desire to overstate hurt in the absence of information, but whatever happened that night was not an act of disrespect to your son. This is about you and your boyfriend, and it’s unnecessary to insert your son as a proxy into a conversation about your feelings.

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