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: Hello, comrades. Let’s knit up the raveled sleave of care together today, shall we?

Q. Divorce and health insurance: After I had an ugly and protracted affair, my husband ended our eight-year marriage. We’ve been living separately for almost four months. Despite many pleas on my part to reconcile, I’ve finally begun to accept that he does not view me as a life partner anymore, for extremely valid reasons. He has drawn up and sent me some very equitable divorce papers and has displayed a lot of patience about my taking some time to sign them. I’m currently employed as a freelancer at a prestigious publication; I’ve been here for more than a year but don’t yet have employee benefits—most pressingly, health insurance. I have gotten some vague promises that I am “next in line” for a staff position but no hard timing and no indication of a move in that direction. I am reliant on my estranged husband’s health insurance to control an intense anxiety disorder and for therapy to help process my feelings on our split. While so much of me is not ready to give up on him, I want to set him free to pursue someone who can be faithful to him and can appreciate him fully. But on the other hand, I don’t want to saddle myself with crippling financial burdens just to maintain my precarious mental health. Is it moral to delay the divorce process until I can secure employee benefits? Should I be looking for another job, even though the stability of a job I love is one of the few bright spots in my life right now?

A: Two distinct points to be noted here, I think: One is that you are still in love with your soon-to-be ex-husband, as much as you are trying to come to terms with the fact that your marriage is over. The other is that you’re in a genuinely precarious financial position. If it were only the first, I’d encourage you to sign the divorce papers as quickly as possible, but as things are, I think you have to adopt a policy of cautious risk-taking. It would be a mistake to delay the divorce process indefinitely, because then you run the risk of exhausting your (extremely patient, it sounds like) ex-husband’s goodwill, and it doesn’t sound like your current employer is in any hurry to offer you a full-time position with benefits. Letting the husband you’re trying to get over pay for the therapist who’s trying to help you get over him sounds like a recipe for trouble, and the sooner you can get on your own health plan, the better. Look for another job with great zeal, and let your husband know that your goal is to find a full-time position elsewhere so you’re no longer dependent on his insurance policy. Ask him how much time he’s willing to offer you, so you have as much information as possible about your future, and so he knows you’re doing your level best not to take advantage of him or spin this divorce out perpetually in the hopes that he’ll want to reconcile. Vagueness is your enemy; clarity and detail are your greatest allies when it comes to planning for your future without your spouse.

I’ll welcome more specific advice from readers well-versed in health insurance policy, so if anyone has a suggestion or other options for this LW, please let us know.

Q. Which pronouns do I use to talk about times before a friend transitioned?: I’m a girl. I had a roommate in college who recently came out as a trans man (let’s call him Joe) and now goes by male pronouns. My question is: When I tell stories from the year that Joe roomed with me, how do I refer to this person? It is especially weird when I mention my freshman college roommate in a story to a bunch of people who have never met him (and will never meet him). Example: “ … then my roommate walked in and he … ” Can I just say she/her/his old name so that I don’t have to explain the situation? Or is that rude?

A: If you refer to Joe by female pronouns, you run the risk of outing him to other people without his consent, which is something I’m sure you don’t want to do. Even if Joe is relatively out to his own family and friends, he may not wish to be outed to a wider set of your acquaintances for reasons of safety and personal comfort. Stick with Joe and he; I don’t think too many people will be jarred by the idea of a woman having had a male roommate in college. Since the situation isn’t yours to explain and Joe no longer uses his old name or female pronouns, you should follow his lead and let him tell his own story.

Q. Photo dilemma: My father is 74 years old and in poor health. I only see him a couple of times a year because I am so busy these days between work and kids, and his health no longer permits him to travel to my home to visit. We are going to see him soon, and I have scheduled an in-studio photo session with a professional photographer for the first afternoon that we are going to be in town. My dad said he was willing to get photos taken with our boys.

Here’s my dilemma: I don’t want my stepmother in the photos, and I’m searching for a diplomatic way to communicate this to him. Long story short: They have been married for 26-plus years, and she and I have never had a good relationship, but in the past 15 months or so, things have deteriorated to a point where I do not speak to her (unless absolutely necessary) and have decided to have no relationship with her going forward. Any suggestions on how to frame this so as not to offend my father?

A: Readers familiar with my general take on things will not be surprised by the following: You must abandon your belief that you will be able to ask your father something offensive without offending him. You can offend him and get what you want, you can offend him and fail to get what you want, you can compromise and not offend him at all, but there is no sequence of events where you tell your father his wife of nearly three decades is not welcome in the family portrait you’ve scheduled for him and he shrugs and says, “All right, then.” Just because you’ve decided not to have a relationship with his wife doesn’t mean you can pretend he doesn’t have one with her. You’ve also hamstrung yourself by asking for the portrait first, then attempting to push your stepmother out of the picture after he’s already agreed. That said, I think there’s a reasonable compromise to be found here. Take your big group shot, stepmother included, and then ask for one of just your father with his grandsons. That’s a perfectly normal portrait arrangement, and one that won’t single out your stepmother as the object of your disfavor. He can keep and display the pictures with both him and his wife, and you can frame the others. Then go back to your usual policy of keeping a polite distance.

Q. Does a baby require both parents at all times?: I just don’t know how to talk to my friend about this. My very good friend had a baby about a year ago. I know babies change friendships; however, I haven’t seen my friend without her husband and the baby since. A whole unit every time we get together. I tried to be subtle about it: “I’m looking forward to a nice girl’s day.” She’s even bringing them to a girl’s weekend away. I have other friends with babies, even younger than hers, and they told me they are looking forward to time off from baby and husband. I’m completely at a loss to know what to say to her or if I can say anything. Any advice is welcome.

A: Don’t be subtle. Tell your friend that you’d love to see her just the two of you, and ask what you can do to make that happen. (As you ask, try to keep resentment out of your voice; you’re asking for some one-on-one time, not reprimanding her for having had a family.) Just because you have other friends who have expressed a desire to spend time away from their children doesn’t mean this particular friend wants the same thing. She may not have the money or the resources to spend much time away from her 1-year-old, and when those rare opportunities do arise, maybe she’d rather spend them getting rest or being by herself. It’s not unusual for the parent of a newborn to spend a great deal of time with said newborn. There’s nothing wrong with what you want, but you should also accept that your friend’s child is going to be a significant part of her life, for the rest of her life.

Q. Re: Divorce and health insurance: If you work an average of at least 30 hours per week, the employer may be obligated to offer you insurance because of the ACA. It depends on the size of the company; the requirement applies to companies with 50 or more full-time employees and/or full-time equivalents. Under the ACA, employees who work 30 or more hours per week are considered full time. This happened to me shortly before I was taken on staff at my company.

A: Thanks for the tip!

Q. I know it’s over, but he doesn’t: I have been in a long-distance relationship for nearly 10 years. We did live together for one year and planned to continue doing so, but I took a new job in another part of the country two years ago. At the time, he was angry about this because he felt he had no choice in where we would live. I had no choice in taking the job either, though, if I wanted to continue on my chosen career path. We had some pretty serious arguments (where he took out his anger by breaking things), and a couple of times he said he wanted to end the relationship. However, each time he changed his mind within a few hours. Two years later, he has warmed up to the idea of moving, but now I am the one with reservations, partly stemming from highly flirtatious texts he exchanged with at least two other women (he doesn’t know I know this). He has been dealing with a stressful family situation and frequently says to me “You’re the only person I have” and “I don’t have anyone else to talk to,” making me really worried about how he will handle a breakup. My solution so far has been to delay the inevitable. I know I’m only making things worse, but I can’t decide how to proceed. Break up over the phone? Fly out and do it in person? Help!

A: This is a long-overdue breakup. Don’t waste any more of either of your time by waiting to get on a plane. End it now, over the phone, and stick to your guns. Take yourself out for a drink or a meal with friends afterward so you’re not tempted to drag out the conversation or kick the can a little further down the road for another decade. There are other people in the world your boyfriend can talk to about your breakup, and I’d encourage you to end things even if he lived in the next room.

Q. Don’t want to move: I met my husband while doing a semester abroad. He ended up following me to the States and finishing his Ph.D. We got married and had a plan to move back to his home country in five years. Since then we’ve had a 4-year-old girl and a 3-year-old boy; I have been a stay-at-home mom with my mother and sisters only two streets away. I don’t want to leave. My husband has increasingly been talking about moving back to his home country since his father is in poor health. If we go, my children will miss growing up with their cousins and grandparents. I don’t want to move. I feel awful because my husband agreed to stay in America when I was pregnant because I wanted my mom nearby. His parents have only seen our kids three times since they have been born. Am I being selfish here?

A: For the sake of balance, I would remind you that if you do not go, your children will still miss growing up with their cousins and grandparents, because they are as much a part of your husband’s family as they are a part of yours. If you’ve changed your mind since you and your husband originally agreed upon your five-year plan, you owe it to him to be honest. You knew when you married him that your husband wanted to go back to his home country one day. You can’t just keep your thoughts to yourself until he’s waiting for you at the airport then pull the rug out from under him. I don’t know what compromise the two of you will be able to reach—whether it’s returning to his home country together for a limited number of years, splitting the time between your two respective countries, or sending the children over to see their extended family in the summers—but I do know that you can’t make this decision unilaterally just because you’re comfortable with the way things are. Your husband is just as much a part of your family as you are, and his family background is every bit as important as yours. Be honest about what you want, be willing to accept that you will not get everything your way, prioritize what’s best for your children over what’s easiest for you, and listen to your husband as much as you advocate for yourself.

Q. Breast-feeding etiquette: I have 6-week-old twins, and I am breast-feeding them. The problem is that my in-laws are anti–breast-feeding. My mother-in-law thinks that breast-fed babies are “malnourished,” and she fears that I am permanently damaging her grandchildren by starving them. My father-in-law is so uncomfortable with breast-feeding that he leaves the house when the babies are eating, even if I am using a cover. When they come to visit us, I refuse to change my nursing routine to accommodate their discomfort. However, I’m not sure what to do when we are at their house. I could hide myself away in a bedroom the whole time (with two babies, I spend a lot of time nursing!), or I can continue to ignore their reactions and plant myself in their living room. It feels a little rude to make them so uncomfortable in their own house when they are hosting us. But on the other hand, I think their reactions are ridiculous and they need to get over it. What do you think?

A: How on earth does your mother-in-law think human children survived before the invention of baby formula? Does she take the story of Romulus and Remus literally? You could, I suppose, offer her a few La Leche League pamphlets to set her straight on the safety and efficacy of breast-feeding, although something tells me that’s unlikely to change her mind entirely. I think you’re right not to change your feeding routine in your own home, but I’m afraid that whenever you’re a guest at theirs, you should defer to them. That doesn’t mean you should stop breast-feeding entirely when you’re under their roof, but if they’d prefer you do so privately, it would be polite of you to comply. When it comes to your own home and the world at large, however, you’re under no obligation to change your habits.

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