Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

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Q. Should I be more embarrassed?: My husband and I don’t have kids or pets. We’d love both or either but we haven’t been blessed, so we sort of started a game of pretend with a beloved stuffed animal. It started as a joke, but four years later, our stuffed animal has a personality, “talks,” and even has a fleshed-out backstory.

We both know she isn’t alive, nor do we wish her to be, but I feel like this is something I should hide from others even though we’re not doing anything that weird. Or is it super weird for adults to anthropomorphize a teddy bear? Why can’t I continue to play my harmless game without guilt? Is this the most pathetic letter ever?

A: This is at worst harmless and at best charming and enjoyable! All adults play various games of pretend. This particular game sounds playful, self-aware, and like it brings you both joy.

It’s also perfectly reasonable to want to keep it relatively private, in much the same way that the voice I use to address my 14-year-old spaniel when we are alone in the house is not the same voice I use to answer a phone call or record the Dear Prudence podcast. There is nothing wrong with the voice I use to speak affectionately to my dog, but it’s a very particular sort of voice that’s only appropriate under very specific circumstances.

As for your more general question—humans anthropomorphize everything. There are blogs devoted to cataloging houses that sort of look like faces! This is a completely average impulse, and it’s not a sign that you and your husband have an arrested emotional development or need to channel your energies elsewhere. You are fine!

Q. Son won’t have children: We are concerned our only son isn’t having children. Every time we bring it up with him, he seems to have a new excuse. Recently when we tried to discuss this with our daughter-in-law directly, she said her high-powered career would be severely impacted if she didn’t plan child-bearing carefully because she doesn’t get paid parental leave at her workplace. We tried to encourage her by saying that she doesn’t even need to work since our son is very successful and we have considerable means. This seems to have offended her greatly. How do we convince them that we only want them to be happy?

A: A great way to convince your children that you want them to be happy is to stop directly contributing to their unhappiness by repeatedly badgering them about their life choices and assuming you know what will make them happy better than they do.

Apologize to your son for pressing the issue, take his excuses at face value—what you consider “excuses” may be, to him, excellent reasons to delay or avoid having children altogether—and apologize to your daughter-in-law for presuming she should quit her job and have children simply because you would find it convenient, and then drop the subject entirely. You have forfeited the right to ask innocently about whether or not they’re planning on having children because you have repeatedly failed to do so politely, respectfully, and appropriately.

Q. I think my dad is forcing me to commit fraud: I moved out of my parents’ house almost two years ago and bought new car insurance at my new address that same month. My dad immediately advised me to add my sister, who still lives at home, to my policy to save us both money, and I didn’t think anything of it at the time because my dad has always handled my financial planning. Now he wants me to add an additional car that will be driven primarily by her fiancé, who lives at a third address, without actually adding him as a driver.

I asked my dad outright if this was fraud—he said no. Everything I’ve found through a cursory Google search disagrees. I’m angry that my dad is being so cavalier about the risks to my record, but there’s no way for me to clarify the legalities without tipping off my insurance provider. What should I do?

A: Don’t add the additional car, and have your sister’s name removed from your insurance policy (it’s possible that I’m missing something, but I’m not sure how adding your sister to your policy saved you “both” money, so much as it saved your father money). In the future, do not take financial advice from your father.

Q. Retirement: I am lucky enough to be looking at early retirement. I have grand plans to travel and not sit at home babysitting. I love my grandchildren wholeheartedly. My daughter’s kids are old enough to take care of themselves while my son’s children are infants. His wife and I don’t see eye to eye. She has firm opinions on parenting practices, which I don’t share, but I learned from my wonderful mother-in-law that the best gifts you can give to your in-laws are an open door and sealed lips.

My daughter-in-law does not share this view. She loves to dictate how other people’s homes should be run, from meals to cleaning products. Now that my retirement is coming up, she has been making noises about “Grandma bonding with the grandbabies,” meaning they want to stop paying for their expensive day care by making me do it for free. If it were an emergency situation I would be happy to help, but it isn’t.

I know it will end in tears. How do I head off this situation without offending my daughter-in-law? My son is useless as a go-between and my relationship with both of them is very delicate; I have no desire to wreck it.

A: There are definitely situations where it’s possible, even desirable, to finesse a nonanswer or arrive at some sort of diplomatic compromise—this is not one of those situations. The worst possible outcome here is not that you say “No” upon being asked to open a day care and your daughter-in-law throws a tantrum. The worst possible outcome is one where you end up giving in despite your misgivings because your daughter-in-law tries to make your life miserable until you say yes, and then things go badly (as you know they will) because she wants both free child care and the right to micromanage the manner in which you provide it.

If your daughter-in-law is a steamroller and your son is “useless,” then it falls to you to become the cheerful-yet-firm enforcer of the word no. “No, that doesn’t work for me.” “No, I’m not able to do that.” “No, I’m going to travel during my retirement.” You don’t need to provide justification or furnish arguments as to why you don’t want to become a full-time child care provider after you retire; you simply need to say “No” and let the chips fall where they may.

It’s possible that all your daughter-in-law ever does is “make noise” about having you replace their expensive day care service (it’s always charming when someone phrases something that would benefit them as if it is something that you secretly want or need, like she’s doing you a favor in giving you “grandma bonding time” by asking you to provide her with free, daily child care). If she never asks you directly, then that’s a bullet well-dodged. But if she does, I don’t see a way for you to “head off” any sort of conflict, because you absolutely have to say no.

Q. Cousins, not siblings: About three years ago, my parents became guardians for two of my cousins, ages 2 and 4. They soon started calling my parents “mom” and “dad.” That’s completely fine by me, as my parents stepped into their parental roles. However, my parents also started insisting I refer to them as my brother and sister, and I can’t do that.

I have been living out of state for years and I have no basis for referring to my cousins as my siblings. I expressed this view to my mother once and she was extremely upset with me and told me I was wrong, making light of family ties. I don’t see it that way at all, and I feel it’s healthy to refer to family members correctly. The children know that my parents are actually their aunt and uncle, so it’s not even like they’re trying to keep it secret. My cousins are not adopted, and may end up moving back in with their biological parents eventually.

I get my cousins gifts, celebrate special events with them, and they’re included in all family photos. When I got married, I didn’t make an issue of it when my mom insisted that my cousins be in all of my wedding photographs involving immediate family, and they’re front and center even though I would have preferred an actual immediate family photo.

I do my best to treat my cousins the same as I treat my siblings, so am I being selfish to refuse to call them my brother and sister?

A: If your parents had suddenly had late-in-life biological children, those children would still be your siblings, even if you did not grow up together or consider yourself especially close to them. Your parents have “stepped into their parental roles” with your cousins; they are now, in every sense, your cousins’ mother and father. Even a pedant can see that; as your cousins are now your parents’ children, they are also your siblings. It’s not “incorrect” to refer to them as such, and you are of course free to clarify with your own friends the slightly unconventional way in which you came to acquire two new siblings a few years back.

You say that you do your best to treat your cousins the same as your biological siblings, but it’s very clear from your letter that you consider this a temporary and inconvenient arrangement—you “didn’t make an issue” when your parents asked to have the children they’ve been raising for three years included in a family photo. It doesn’t sound like your parents are asking you to treat your youngest siblings the same way you treat the ones you grew up with, or that they’re asking you to refer to anyone “incorrectly.” I think you have a real opportunity to let something relatively unimportant go here, and you should take it!

Q. Regret: I got pregnant 10 years ago and let my husband pressure me into carrying it to term. It was the biggest mistake of my life. I never bonded with my daughter. I listened to my mother, the nurses, my doula—the bliss, the love, the affection was never there. I looked at my baby and only saw a greedy, grasping nightmare and I hated myself more for feeling that way. I went to work as soon as I was able and got a live-in nanny.

I tried asking for help from my husband and mother once. They tried to pass it off as postpartum depression because “only a monster could not love her child.” I tried going to a therapist twice, only to get a similar reaction. My husband left without looking back when our daughter was 4. I offered him physical custody, he declined. He moved away and skipped seeing her except on holidays and for a week during the summer.

He remarried last year in a big production. His new wife seemed to genuinely want my daughter, at least until she got pregnant. Now they have “scheduling conflicts” when his turn comes around. My daughter hasn’t seen her father in six months. My mother and our housekeeper do most of the heavy raising with my daughter. My work involves a lot of travel, often weeks at a time. I try to play the part of attentive mother—I talk to my daughter over the phone or Skype, make notes on important events at school, remember the names of friends, et cetera.

My daughter, by all accounts, is a healthy, happy child. I am terrified of screwing her up. I tell her that I love her back when she says “I love you, Mommy” and it is completely devoid of any emotion. I am numb. I can’t see a light at the end of this tunnel. Maybe you can. I don’t know what to do. Please help me.

A: Let’s start by taking a look at all the things you’re doing right. You’ve developed a shared child care/housework arrangement between your mother, your housekeeper, and yourself that seems to be working right now. Your child is doing well in school and you two, while not the closest mother-daughter pair, talk regularly and have positive interactions, and you’re involved in the workings of her daily life. You behave lovingly toward her even though you did not want to become a parent and don’t feel an emotional connection with her. Frankly, if you’re terrified of screwing her up, that’s a pretty significant indicator that you do care for her. You may not feel a rush of emotionalism when you think about her or want to be a stay-at-home parent, but you care deeply about her well-being and don’t want her to come to harm—that’s a very real sort of love. There’s a lot of good here. That doesn’t mean that your anxieties aren’t justified, or that your daughter isn’t already aware on some level that you don’t feel warmth and affectionate toward her, but I think you’re being much harder on yourself than you need to be.

When it comes to making sure your ex-husband is holding up his end of your custody agreement, I think your best bet is to consult with your divorce lawyer and figure out what options are available to you. I also think, even though you’ve been burned before, you should seek out a new therapist and be very clear from the outset that you want to be able to discuss the fact that you don’t have strong, loving feelings for your daughter, and are looking for strategies to manage your feelings of distance, detachment, and guilt while also remaining a stable, involved presence in her life. You have the right to get therapeutic support without judgment. Hiring nannies and housekeepers and getting your mother to help (as long as she’s willing and able) are perfectly legitimate things to do, and you should continue to take help where you need it. As your daughter gets older and more self-sufficient, you’ll be able to develop a different sort of relationship with her, one that’s based less on dependence, which should go a long way toward removing that trapped feeling.

Q. He’s engaged but won’t leave me alone: I (25, female) have been seeing this guy for almost two years now. He (33, male) has a girlfriend of eight years, and they recently got engaged. I was very hurt, and I told him to leave me alone, but he wouldn’t stop contacting me. He would contact me on different apps when I didn’t respond.

Over these two years, we tried to break things off multiple times, but we’d end up getting back together somehow. I even moved to another country a year ago just to stay away from him because I love him too much. He was devastated when I told him that I was moving away. He texts and calls me when he’s with his girlfriend even when they were going on trips together. And we’ve met up in various countries this year; we went to L.A., Dubai, Bali, and Hong Kong together (we were originally in Australia). He also checks on guys whom I’ve gone out with and gets jealous.

I’m single and feel like I’ll forever be single because of him­. Does he really like me? If he likes me, then why did he get engaged? What does it mean when a guy goes through all the trouble to keep a girl in his life but then proposes to his long-term girlfriend?

A: It means he’s a jerk who is going to continue to waste your time for as long as you accept his calls, agree to meet up with him, and tell him which guys you’re seeing. He may like you, but he doesn’t care about your well-being, and he wants to keep you constantly available to him on the side while he marries someone else. If you don’t want that for your future, then it doesn’t matter how far away you move—the real distance you need to set between the two of you is emotional.

It’s incredibly difficult to break a long-term habit like the one you’ve established with this guy, especially when you’ve become addicted to the inconsistent hit of attention you get from him when he reappears in your life—alternately distant and wildly jealous—so ask for help from friends, family, and a therapist as you set and enforce a real no-contact limit with him and figure out how to live your life in such a way that you’re not writing to me in another 10 years about your now-married boyfriend.

Q. Re: Retirement: Make plans. Loudly. Obnoxiously. Ask your daughter-in-law if she thinks Fiji is better than Tahiti. Keep the momentum moving so your daughter-in-law can’t derail you. When she tries to spring the “bonding with the grandbabies,” play dumb—“I am so sorry, daughter-in-law, but I can’t. Going to Fiji, remember I asked you about it a month ago!”

A: I think this is a great strategy after the original clear, direct “No,” but it’s absolutely a good idea to make your own plans for your life clear and not to simply clam up and let your daughter-in-law direct the conversation about what you’re going to do with your retirement.

Q. Is it cat stealing if the cat keeps coming back?: My landlord/neighbor has an outdoor cat who is very friendly (and has a heated outdoor house of his own). Last week it was minus 40 degrees for several days, and when I came home, the cat was sitting on my porch making strange sounds. I invited him in, thinking he may be dehydrated; he drank two bowls of water and then went to sleep on the floor.

He hasn’t left. All he wants is to sleep on the floor or couch and cuddle. I have put him outside on warmer days, but he comes back every day. I spoke to my landlord and told her where her cat was, and she said it was fine and she wasn’t worried. Did I steal this cat? Or am I ethically in the clear to keep letting this cat inside?

A: If you spoke to the cat’s owner and she’s OK with him staying with you, then by absolutely no definition have you stolen anything. You are doing fine!

Mallory Ortberg: Thanks, everyone! See you all next week.

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

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