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 gay best friend proposed to me: I am 35 right now, and my best friend “Tom” is 39. We have been best friends since our college years, survived career changes, the death of parents (mine), cancer (him), and never finding true love. Tom’s lover left him during his bout with cancer, and I wasted the last five years with a guy who lied to me about wanting kids and marriage. I have always wanted to get married and have kids. Tom wants the same thing; only Tom is gay. We always joked about having kids together if we hit 40 without finding true love. But Tom is serious now. He has brought it up a couple of times and thinks we should do it. He says he loves me, trusts me, and it would be too hard to raise a baby as a single parent. It would be a partnership to raise the kids together and an open marriage. His insurance is better than mine and only for legal partners and families. We would do it artificially, and together I could afford to stay home with the baby. Tom is basically my only family now that my parents are gone, other than some cousins I exchange Christmas cards with. Am I crazy to consider this? I want to be a mom and Tom would be a great dad, and I don’t want to take my chances in the dating pool again. We could always get a divorce if either of us found love. I just feel that my heart is overtaking my head here. Am I being rational?

A: It is not crazy to consider a nontraditional family arrangement, not by a long shot. It’s also not something you should enter into lightly or without careful deliberation. If, in the back of your mind, you consider marriage and children with a romantically and sexually available partner to be your first and best option, and Tom’s solution a mere forestalling of the worst-case scenario, then you should carefully interrogate your own goals, desires, and expectations. Consider going to premarital counseling together for six months with a queer-friendly therapist who understands what kind of family you two are trying to develop before moving forward. It’s a good idea for any couple contemplating marriage and co-parenting, regardless of whether they’re romantically involved or not.

Talk seriously and at length about what an open marriage would look like. How much time would you be willing to grant the other to devote to dating while your children are very young? What would you do if one of you met someone they felt serious about while you were pregnant? While your children were infants? How will you two resolve disputes and handle the division of household labor? Have you ever lived together before? In the event of an amicable divorce, would one of you seek child support? What sort of custody arrangement would you be able to agree upon? These are all questions it’s crucial to address before you make any permanent decisions.

That doesn’t mean this is a bad idea, or that you shouldn’t consider it—I think it sounds lovely, and you and Tom seem to have a solid, long-term foundation for a lasting co-parenting partnership. But there are a lot of potential pitfalls, and you might run into more complications than the average romantic couple. That absolutely doesn’t mean you can’t consider it, just that you should plan for maximum difficulty and hope for the best. If you two can successfully develop some mutual goals, establish parenting compatibility, and figure out a level of commitment to one another that would work for both of you even once (or if) you start dating again, then I think you should move forward with cautious hope and joy.

Q. Previously married?: I’ve always had an interest in genealogy, and since I already know as much as there is to know about my family, I started looking into my partner’s family. He gave me some names, and for the past few days I’ve been telling him about information I found, and we were both quite excited about this. However, I might have just found out that his mom was previously married. All the facts seem to line up, but I’m not sure what to do with this information. My partner comes from a very religious family, where divorce is looked down upon. I don’t want to keep information from him, but I also don’t want to cause tension in his family by bringing this story to light, especially since I don’t know if it’s true. His mom passed away a couple of years ago and is thus unable to confirm it. I’m assuming that if she was previously married, her husband/my partner’s dad would have known, but what if he didn’t?

A: If it were me, I would put this potential bomb back and gingerly step away from whatever drawer I’d stashed it in. Given that your partner’s mother is dead, the absolute best-case scenario of this situation is as follows: You tell your partner you found out his mother was previously married, he confirms it, and the two of you speculate for a while about what that marriage might have been like. That’s it. That’s the best possible outcome. The only other possible outcomes are gossip, hurt feelings, sudden revelation of further secrets about the dead, and resentment. Since this happened before your in-laws got married, it’s not information that could change your partner’s understanding of his parents’ relationship and thus doesn’t seem crucial for him to know.

Given, however, that you are not me, if you think your partner would be able to handle this sudden revelation and wouldn’t necessarily demand his father offer an immediate explanation, you might consider discussing this just between the two of you. You know your partner better than I do, so only bring this up if you think there’s a decent chance he could absorb this information without feeling rocked, bearing in mind that the only person who could provide him with any sort of detailed explanation is now dead.

Q. Trying not to insult: Is there a rule on how to politely give “hand-me-downs” to people I encounter daily who are less fortunate financially? Example: I am fortunate enough to live a fairly comfortable life and because of a hectic schedule have a cleaning lady come to my home every few weeks. This young lady is lovely and very professional at her job. Since we chat during most of her visits I have gotten to know that she and her family are in a financial hardship (most of the time) and that she is constantly working to make ends meet. I know that things such as clothes/cosmetics/perfume are very expensive for her and a rarity. I happen to have several bottles of nice perfume (various gifts, etc.), which I never used and which are sitting on my shelf collecting dust. I would like for her to take them if she likes them but am unsure how to offer them without insulting her—I don’t want her to think that these are pity gifts or hand-me-downs I want to get rid of. She is a very proud person and I don’t want her to take it the wrong way. (I already pay her for her work.) I have several other things that I think she may like, but I have no idea how to offer them to her?

A: If you know this woman well enough that you’re worried she’d be offended by the gift of secondhand perfume, then I think you should trust your own judgment and not run the risk. If you’re looking to help her out financially, consider offering her a quarterly bonus or the occasional tip the next time she cleans your house.

Q. Good friend didn’t take my side in a dispute: I have a work friend that (until recently) I had been very close to both at and outside of work. We worked in cubicles next door to each other for about a year and half before I applied for a promotion and moved to another department at the same organization. While we didn’t see each other quite as often anymore, we still regularly met for coffee, lunches out, and social events outside of work. A few months into my new position, I got into a serious dispute with another co-worker concerning intellectual property rights and an article I had written. It’s a long story and could be the subject of its own question, but the end result was that the organization’s legal department sided with me, and the co-worker I was disputing with left the organization voluntarily. A few weeks after this dispute had been resolved, I was out to lunch with my friend, and as we hadn’t chatted in a while, I asked her if she had heard about this dispute. Turns out that my friend had not only heard about the dispute but had been communicating with the long-gone co-worker about it and had taken her side against me! I was shocked because I didn’t even know they were friends—and then I find out she took this other person’s side without even asking me about the dispute to hear my side of the story? I was so hurt that I haven’t spoken to this friend for the past few months. When she does try to approach me at work, I am polite but keep my distance. Now she has emailed me an invitation to something and seems to want to be friends again, yet she hasn’t mentioned the dispute—either to apologize or explain herself. Should I accept her invitation and see if she apologizes? Or keep my distance and consider the friendship lost?

A: An invitation is not the same thing as an apology. It sounds like your co-worker would like to resume some version of your previous friendship but does not believe herself to have done anything wrong. If you’re not interested in picking up where you left off unless she’s willing to apologize and hear your side of the story, I think you should decline the invitation and continue to remain professional but distant.

Q. New love and expectation of moving to another country: I recently started dating a wonderful man. As we have become a bit more serious, he inquired how I might transfer my ability to practice law to his country. I recently researched it, and it is incredibly hard to become licensed to practice law in his country. I don’t think I could do it. Is it reasonable to ask him if he would consider moving if our relationship became long-term due to my inability to become licensed (or extreme hardship in doing so) in his country? He currently works in both the U.S. and his home country, so it appears his career would permit him to find work in the U.S.? Should I not move forward with this relationship?

A: Yes, of course you can ask him. He already brought up the subject, so you don’t even have to go to the trouble of introducing the topic of moving. If it’s debilitatingly difficult for you to transfer your law degree to his country, but he’s already got a professional foothold in yours, it seems only practical that you two would consider the possibility of his moving to the United States full time. He may have had no idea that getting licensed would be so close to impossible. Everything you’ve described about him thus far sounds reasonable, so tell him what you’ve learned and see if he’s interested in considering other possibilities.

Q. Re: Trying not to insult: As the poorer friend who just learned of massive Goodwill donations of things that my household could have used, I think it’s OK to ask gently if someone is interested. She can always say no, but it’s really killing me to think that I could have saved hundreds of dollars and instead—POOF.

A: That’s a helpful perspective, although I think it’s worth bearing in mind that accepting a donation from a friend is situationally different from accepting a donation from an employer. There’s a difference, too, between useful household items and luxury perfume—tastes in perfume can be so subjective that I think the risk outweighs the reward. But it’s a point in the “Go ahead and offer” column!

Q. My friend doesn’t get that he broke up with her: I have a wonderful friend who recently broke up with her boyfriend of over five years, which was great, because it was such a terrible relationship, really unhealthy and toxic. She immediately started dating another guy. I was hoping that it was just a rebound, but when that relationship ended up fizzling out, she just wouldn’t get over it. He broke it off by saying that maybe, when they were both in a healthier place, they could get back together. She is so hung up on that and won’t get over it. My friends and I are trying to encourage her to enjoy being single—invest her time in hobbies and her mental health—but she will only do it in the context of being better for him to come back to her. I want to just tell her that he broke up with her, he won’t ever come back, but I don’t think she’ll believe me. All she does all day is worry about him and his mental health instead of herself. Worst of all, now her other ex is starting to text her again. How do I support her? How do I get her to just stop thinking about him and to focus on herself?

A: You can offer your own opinion clearly but no more than once (“I don’t think it’s a good idea for you to text Monstro No. 1 back, but it’s your call”) unless invited to give further advice. Beyond that, you can offer her a generous berth to make bad decisions and limit the amount of time you spend listening to her talk about Monstro No. 2. If you’ve previously been willing to listen to her discuss his impending return endlessly, she may kick at the prospect of having an ever-present ear taken away from her, but hold fast. You may not be able to convince her to see her situation the way you do, but you can absolutely tell her, kindly but firmly, that she’s been talking about him in circles for weeks, which doesn’t seem to be helping any, and if she’s looking for further help processing the end of the relationship, she should talk to a professional about it.

Q. Re: Trying not to insult: I disagree. Ask your cleaning woman if she is interested in having first refusal of things you want to get rid of. If she says yes, then as long as these items are new and unopened (perfume, etc.), or in good usable condition (clothing, furniture), and she can say, “No, thank you” without offending you, then this can be a respectful interaction.

A: That’s a polite, open-ended way to offer! Thanks for the suggestion.

Q. Travel woes: I’m a college student and attend school very far from home. Summer break is coming soon, and I’d really like to take a weekend trip to a nearby country with my boyfriend of six months. The only thing stopping me from going ahead with booking is my parents. They’re pretty conservative and aren’t very keen on me traveling alone with him, sleeping in the same room as him, etc. We’re not very interested in inviting any friends along because our friend circles don’t really overlap, plus some friends end their semesters in different weeks. I can’t just book my tickets and go ahead because my parents control my bank account and getting a few hundred isn’t possible. My boyfriend and I are stuck on how best to convince my parents that it’ll be a healthy and safe trip, because we both really want to travel together for the first time. Any advice?

A: Are your parents your sole source of income, or do they merely have controlling access to your joint bank account? If it’s the former, then your options are slightly more limited. If it’s the latter, you might be able to visit a local branch and find out how to either set up your own, separate account, or how to make deposits and withdrawals without parental permission. Assuming your parents don’t just manage your bank account but also put money in it, you can try any one of the following:

Talk to them honestly about the trip you want to take, stress how safe and responsible you plan on being, and ask them to consider changing their minds. While you’re at it, you might reconsider inviting some of your nonoverlapping friends as a buffer. It’s only a weekend trip, not a month backpacking together and living out of one another’s pockets.

Ask your boyfriend to book the tickets on your behalf, if he’s financially able to and willing to consider it a gift or a long-term loan.

Skip the trip this summer, but start saving up money in a separate bank account so that you’re able to take future trips without getting your parents’ permission first.

Mallory Ortberg: That’s it for today, everyone. Thanks, and see you here next week!

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