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.

Mallory Ortberg: Welcome back, you seekers of wisdom and truth. Let’s chat!

Q. I’M the gay sister: I’m writing to you because I am too embarrassed to say this to anyone I know. I’m an out lesbian, and I have been for years. It’s been a process getting my family on board, and some still aren’t. My younger sister is amazing and supportive, and has been with her boyfriend for a few years. I’ve got a lot of resentment toward how our family has treated our relationships (her boyfriend is included in everything the family does, he’s allowed to sleep over, etc.) while my partner didn’t get the time of day. Well, my straight sister just told me she’s not so straight. Outwardly, I’ve been super supportive, and love her to bits, but I can’t shake the negative feelings I have about her being bisexual! I’m not biphobic at all; it’s something about our family dynamics that has put a negative taste in my mouth. Am I crazy? How do I get over this so I can support my wonderful sister the way she deserves?

A: Your reaction is completely understandable and not “crazy” in the least. You can both support your sister’s bisexuality and acknowledge that, because she’s dating a man, your family affords her a great deal of straight(-appearing) privilege that has never been available to you. That’s not her fault, which you’re well aware of, but it’s still painful and isolating. You’re doing everything right by supporting your sister and trying to figure out how to process your feelings of resentment in a way that doesn’t involve her. Discuss them with a therapist or friends who don’t have a direct connection to your sister. Be aware, too, that if and when your sister ever comes out to your family, the kindness they’ve extended toward her boyfriend may shift or even evaporate. It’s also worth pointing out that you have the right to ask for your sister’s support as much as she’s asking for yours—your homophobic family is a problem that affects you both in some different and some overlapping ways, and you may find yourself less resentful if you lean on her when you’re being excluded.

Q. Do we owe an explanation?: My boyfriend and I are in our late 20s and live together. We’re close to getting engaged. I’ve known since I was a preteen that I don’t want to have kids, and my boyfriend doesn’t want them either. My family is aware of this, but most of them assume I’ll change my mind or that my boyfriend will (and some tell me so when the subject comes up). His family doesn’t know, and his parents are big on grandchildren. Once we’re married, I know this will become an issue on both sides. I hate being told I’ll change my mind—I know I won’t. What is the best way to deflect these questions that already come up and will only become more insistent?

A: Your boyfriend should tell his parents, certainly, at some point before you are married that he does not plan to provide them with grandchildren. You are right in anticipating that it usually takes more than one conversation to convince someone that one is genuinely uninterested in having children and not merely offering an interesting thought experiment. The best deflection for “You’ll change your mind” is polite nonengagement along the lines of “I’m sure anything’s possible, but we’re both confident and secure in our choice, and have been for years—thanks for asking.” (It will be perhaps tempting to speculate on the number of people who have had children and then changed their minds, but I do not think this is a conversational avenue you should be exploring.)

If anyone in the reading pool has found success with a particular deflection when told “You’ll change your minds,” please share!

Q. My best friend might hate me: My friend and I are both 17, although because I’m in my third year of college, and she’s a senior in high school, we are only a part of each other’s lives if we want to be. We have been friends off and on for eight years. We are currently extremely close and spend time together almost daily. Last July, we had become friends again, and we were drinking at her house. She fell asleep, and I made the decision to text her friend and sister that she had been texting to tell them that she was asleep and they didn’t have to worry if they didn’t hear back from her until tomorrow. Not sure why I did this, but she saw the texts the next day, said that it was weird, as I agreed, but she had no issue with it, and wasn’t mad. However, while texting her friend I saw my name in the conversation. Curious, and drunk, I read some messages and found out that my friend had said many hurtful things about me. She thought I was irritating and, when we became friends again, she “hoped I didn’t become obsessed with her like I was with my last best friend.” I brought her coffee one morning, and she said that this was creepy and weird. She said other things that weren’t horrible but stung and I felt stupid and was upset, but never mentioned it. I am very happy with the friendship I have with her, and I’m not mad, but I feel guilty about reading the messages, and, while I’m fairly certain she’s equally as happy with the friendship as I am, knowing she said these things about me is hurtful. I have no idea if I should bring this up or not. Please help.

A: I think your friend’s fear that you would disregard her boundaries and your inexplicable decision to send text messages on her behalf are very much linked. What you did was unbelievably out of line, and even if your friend claimed not to be angry in the moment (which she may have done simply because she felt too uncomfortable to tell you), it’s clear that she is profoundly worried about your ability to behave appropriately, as evidenced by the texts you read. You say you’re “not sure why you did this,” but I think that’s disingenuous. You wanted to know what your friend was saying to other people about you, and you wanted to assert a level of control over her communication and relationships with other people, and she was asleep and you could get away with it, so you violated her privacy in a grossly unacceptable fashion. You should scale back on how often you see your friend until you have a better handle on how to behave, and to that end I encourage you to pursue therapy so you can get help in respecting other people’s privacy and limits.

Q. Kids and me make three(’s company): I’ve been seeing a lovely man for over two years. We’re both divorced. He has two children (10 and 13) and I don’t have any. Due to a canceled job relocation, we went from living together in my city to living apart. With my encouragement, he moved to the same small town as his kids, where his ex-wife has physical custody. All are getting along well, but our future gives me a lot of anxiety. I do not want to move to snow country, and it’d be hard to find work in my field (I’ve looked!). But I feel a lot of guilt about asking him to come back to the city since I didn’t relocate, especially since he doesn’t share custody. He’d go from seeing them regularly in his own place to twice monthly flights to a hotel. It seems like a zero-sum game. I don’t want his kids to lose out, but I’m feeling left out.

A: There is, I’m afraid, a high probability that the two of you will break up, and with that in mind you should both be as honest as possible about what you are and aren’t willing to do to save yourself anguish and uncertainty. If you’re not able to move to where he’s living now, make that clear. If he’s not able to leave his young children in order to live with you again because his role as father trumps his role as boyfriend, then you two will have to decide if you want to date long-distance for the foreseeable future or amicably part ways.

Q. Re: Do we owe an explanation?: When I was married to my first husband, his family, particularly his grandparents, were eager for grandkids. One day I’d had enough and replied to his grandma’s umpteenth “When are you having kids?” with “Nine months after hell freezes over.” Never asked again.

A: This would certainly end the conversation!

Q. Re: Do we owe an explanation?: First I and then both my husband and I went through this with family/friends. I cannot tell you all the creative arguments that have been thrown at me/us! In the end, just let them have the last word of “You’ll change your minds.” In the end you will have the last action—choosing not to have kids.

Q. Boyfriend still on internet dating sites: I have been divorced for a year and have been dating a man for about six months. He is kind and loving. We met on a dating site. A few months back I spotted him on the site, scrolling through pictures of women. I got upset and asked him to delete the site. This past weekend he was on it again. He told me he went back on the site out of boredom. I asked him to delete it again. A few days later I got incredibly angry with him because it’s not out of my head. He has also been looking at porn. I told him I considered this cheating. What should I do? I don’t want to break up with him, but I don’t want a cheater on my hands.

A: If you don’t want to break up with him but you also don’t want him to cheat on you (according to your specific parameters of cheating), you have created for yourself an impossible situation. You’ve asked him not to trawl for dates online—or at least not actively contemplate trawling for dates online, as you don’t know whether he crossed the line from thinking about it to doing it—and he hasn’t stopped. If you consider viewing porn to be cheating, and he idly scrolls through dating sites to pass the time, you two simply aren’t compatible. It’s only been six months; people have ended such short-term relationships for much less. Thank him for a fun six months and exit gracefully, instead of having this exact same fight with no resolution every couple of weeks for the rest of your relationship.

Q. Helping college-age son come out to himself: My son is a college student in a conservative state. The state he grew up in is also conservative. My husband and I have always thought there was a good chance our son might be gay and have tried to communicate our openness in case he was ready to come out. He never has, perhaps out of fear of rejection from friends and acquaintances. In college, he has dated women, and it seems to make him anxious and miserable. I think he might be in denial. Is there any way we can help him?

A: You can ask him if he is gay. I don’t know what you mean when you say you’ve tried to communicate your openness—have you smiled sympathetically when LGBTQ characters show up on your TV screen? talked up your queer friends and co-workers? quietly hoped for the gay best?—but if you haven’t said to your son, “We love you, and if you are gay or bisexual, we would be thrilled and supportive, and if you are not, we are thrilled and supportive,” then say so now, explicitly. Years of overt homophobic messaging from every corner of society aren’t always easily overcome by the vague, implicit communication of “openness.” If you haven’t been making it abundantly clear that you would support and cherish your son if he were gay, but just hoping he would pick up on your supportiveness, start making it clear now.

If he does not take the opportunity to come out, do not force the issue—no one, regardless of their sexuality, likes to be told that they must admit to a particular orientation. It’s possible that he’s never come out due to fear of rejection, but it’s also possible that he’s never come out due to being heterosexaul, and you should take him at his word. He may be anxious and miserable from dating women, or he may be anxious and miserable because he is a young person in a terrifying world. Don’t insist that he must be gay and that he must come out. Even if he’s simply not ready, it’s his decision and you have to let him make it.

Q. Re: I’M the gay sister: I know how you feel. I have a gay sister who came out at 38, while I was a gay man narrowly surviving the AIDS crisis, dealing with discrimination in work and school, and fighting with our parents constantly about my boyfriends for years. I think it’s OK to point out to your sister that you’ve been out longer and had to fight many more battles than her so far. But look beyond that—she’s still your sister, she’s queer like you, and she probably needs the benefit of your experience. It’s worth going the extra mile for queer family, even if they’re late to the party.

A: Thank you so much for sharing this generous, hard-won perspective.

Q. Could this be it?: I am a 30-year-old divorced mom of three wonderful children. I recently started dating a man I met on Tinder and we decided to become exclusive two months ago. I have never been treated so well. He opens doors, waits for me to get off the elevator first, makes me French-press coffee and delicious breakfast in the morning, is truly interested in how my day has been and cares about my academic success. I could really see myself with this man for the rest of my life. However, he has no children and has never been married. He’s 34. This scares me a bit, but as he is otherwise amazing, I’m not dwelling on it too much. My question is more concerning my children. When is an appropriate time to introduce children to a new beau? Of course we would take it very slow, not overwhelming either him or my babes by keeping the initial meet and greets short, dinner or an outing together. But when? Is a few months too short? Is six months better? I think he is really in this for the long haul, as I am. We’ve talked about the future, having to move away as a family unit for my graduate school, and he’s said emphatically that he’s “in.” I’m excited what may come, but also want to do the absolute best by my children.

A: If you think this guy’s in it for the long haul, then there’s no reason to rush an introduction. Being unmarried at 34 is hardly a mark of suspicious character, and he’s made it clear that he’s happy to keep dating you, even knowing that you have three children, and that he’s looking forward to meeting them and understands that you come as a package deal. All signs point to cautious optimism! At two months in, however, you’ve only seen him on his best behavior. That’s not to say he’s probably a secret jerk, just that you’ll do better to see how things go over a slightly longer period of time (what’s he like when he gets sick? When things are stressful at work? When taxes are due? When it’s, I don’t know, summer?) before introducing him to your children. Your instinct to start the introductions off brief and low-key is a good one, and I think the six-month mark is a reasonable one. Go slow—you have plenty of time—and only take next steps when you feel comfortable. Trust but verify!

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