Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.
Daniel Mallory Ortberg: Good morning, everyone! Let’s chat.
Q. Happy: I am a 38-year-old widow. The day my husband died was the happiest day of my life. He was a miserable, vindictive man whose greatest joy was tearing me down. He cheated on me constantly and would cheerfully recount all my inadequacies compared with his mistresses. If I left, he would “pursue me to the ends of the earth.” He never hit me, for what it is worth. At the end, I was isolated and alone; my only social outlet was my family. They all knew how horrible my marriage was, which is what makes their reaction now more hurtful.
I am going to travel. I am going to visit exotic places, drink wine, and learn a foreign language. I have enough money to be quite comfortable for the rest of my life. I would rather shoot myself than ever get married again. My family acts like I am an idiot—they have all sorts of “concerns” about my emotional state, since I not mourning adequately and pearl-clutching over my plans (I am going to Italy). They keep telling me I need to take time and get “my head on straight.” My sisters express discomfort when I say I am happy my husband died when he did or if I joke that I am surprised it was a heart attack since I never thought he’d have one. They hated him! I have an accountant and a lawyer; I am well-advised about my finances. I lost 15 years to the man. I don’t want to lose another five months because my family has a skewed sense of decorum. Please help me get through to them.
A: Don’t worry about getting through to them. Worry about making sure you’re well-packed for your trip. If your family feels uncomfortable when you make jokes about your husband’s death, I do think it’s reasonable to limit your more-off-color comments for close friends (or a therapist) who understand why gallows humor is called for in this situation. It may be one thing for them to acknowledge your marriage was an unhappy one, but they may be unable to join in making jokes about him with you. But beyond that, you don’t need them to agree with you that the time is right in order to get on that plane. If you think it will help, you can share a little bit more about how painful your marriage was, how free you feel now, and how committed you are to making the most of your life as a widow, without making any jokes or trying to relieve the tension with humor, if you think there’s something that they’re missing from the story. But you don’t have to lose another five months; you can still get on a plane even if your family thinks your behavior is shocking. You can tell them you appreciate their concern but have no interest in taking more time, that your head is on as straight as you’d like it to be, and that you’ll send them all a postcard from Milan.
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Q. Silence surrounding long-ago loss: My girlfriend and I have recently started to get more serious, and as a result, I’ve spent more time with her wonderful parents and older brother. I love her and her family very much. A few months into our relationship, she shared with me that she had another sibling who passed away as an infant. Her family never talks about this sibling, and you wouldn’t know they existed from the family pictures in their house (she and her brother are featured prominently) or anything they say. I want to be respectful of her and the pain she and her family must have experienced with this loss, but I’m also confused by the silence that surrounds it—it’s very different than the way I’m used to processing loss. I’m trying to follow her lead (she’s only mentioned her sibling a few times) but I find myself thinking about the infant whenever she and I go out with her brother. How do I navigate this respectfully? Is it ever appropriate for me to mention her sibling in private?
A: It might be different if your girlfriend had ever gotten to know her sibling, but it sounds like they died either before she was born or when she was young enough not to remember them—it doesn’t sound like she has much she needs to process or share with you. That doesn’t mean this is a permanently off-limits topic, but if you’re thinking about this every time you go out with your girlfriend and her brother, you’re probably thinking about it more than they are. I think you have grounds to ask (just her, not her brother) some time when the two of you are alone: “Would you be comfortable with me asking a few questions about your other sibling, and how your family has dealt with that loss? I’m curious to know more, but I don’t want to push if it makes you uncomfortable or feel like I’m being nosy.” Then think of two or three basic questions about what she remembers and how her family talks about it (or doesn’t). But it may be that while this was a serious and devastating loss for her parents, your girlfriend has a more distant, abstract sense of grief around a sibling she never really knew, and that it doesn’t take up as much space in her mind as it does in yours; if that’s the case, I think you’ll have to accept that you sometimes think about it more than she does, without implying that she ought to be thinking about it more.
Q. Overly intimate acquaintance of social media: A man I didn’t know well during college over a decade ago dated one of my not-that-close friends. As I recall, their relationship wasn’t great, and they broke up after a few months. At most, he and I spoke casually in group settings a handful of times years ago. In the past year or so, he has followed all my social media profiles, and he repeatedly writes kind-sounding but overly intimate messages: “Thinking of you all the time, beautiful,” “So proud of your accomplishments, keep crushing it,” etc. I never respond and have blocked him on several sites, only to have him create new accounts and refollow me. I don’t like that he is creating a false public impression of intimacy between us, and I don’t know how to respond. Do I tell him to knock it off? Report him? Keep blocking? Ignore it? I don’t know what to do.
A: Certainly, if you’ve never told him that these comments are unwelcome, then I think it’s time to send him a straightforward “Knock it off” or, if you’re feeling diplomatic, “Maybe you think you’re being friendly by telling me you’re proud of me over and over again, even when I don’t respond. But we don’t have a relationship of any kind, and it’s really creepy when you say things like ‘Thinking of you all the time’ or call me beautiful. I’ve had to block you repeatedly, but you’ve continued to make this sort of comment. You need to stop.” If you still have any mutual friends in common, you might ask them to follow up with him and make sure he knows he needs to leave you alone or he’s going to start hearing about it from other friends. You can also ask your friends or followers on whatever social media platforms you use to report any comments from his various accounts along the lines of “So proud of how you’re crushing it, gorgeous,” venting if you think it would help (“This guy who dated a friend of mine 10 years ago keeps popping up to call me gorgeous and tell me he’s proud of me; it’s so bizarre being told by some near-stranger that I’ve won his approval over and over again when we don’t have any kind of relationship!”), and continuing to block him whenever he pops up.
Q. Get over it: I am 27 and never been married. My boyfriend is 29 and divorced. In the most awkward introduction on earth, I met my boyfriend’s mom, “Leigh,” while we were having sex (his mom used the backup key to bring in groceries). I was embarrassed at the time, but three months down the line, I am annoyed. Leigh acts like I am this evil seducer after her little boy. She is cold toward me and makes sure to get in these little conversational digs. My boyfriend has stood up for me and called her out, but that only makes her worse. He tells me that Leigh will warm up to me in time, but part of me is sympathizing with his ex-wife now. (My boyfriend claims the marriage fell apart due to their career demands.)
I am starting to fall in love here, but the evil mother-in-law jokes are starting to feel less funny and more fortunetelling to me. I am attractive, educated, and kind, and I have never had a boyfriend’s mother act like this toward me. I have gone to church with Leigh, baked her a cake, and volunteered to help out with her charity marathon run. So far it has only gotten me sore calves and more uncivil behavior. I don’t know how to win over this woman, and in all honesty, I just want her to get over it. For someone who claims to want grandchildren, she certainly is trying to run off anyone who might give them to her. What should I do?
A: I know it’s a cliché at this point, but I don’t think you have a Leigh problem. I think you have a boyfriend problem. You (understandably) have a lot of negative things to say about your boyfriend’s mother, but you don’t say a word about why this 29-year-old man lets his mother keep a key to the house or bring over groceries for him unannounced. I assume if there were extenuating circumstances or reasons why he couldn’t comfortably shop for himself that you’d mention them, so it looks like he’s just perfectly happy to let his mother continue to dote on him like he’s still her baby boy. If his version of “standing up to his mother” is objecting when she insults you but still continuing to spend time with her (and letting her keep her key to his apartment!), then his version of “standing up to people” looks an awful lot like lying down. Leigh is doing you a favor in the long run. Let her run you off! Run far away and find a guy who doesn’t give his mother a key to his house.
Q. Love this man, cannot deal with his kid: In December 2014, I had lunch with an old friend from college. I suggested we catch up, not really expecting a lunch to be a date, even though he did. Upshot: great relationship ensues. Over the next four years, my kids grow up, move out, and are now independent; he still has one at home who has severe depression and bipolar disorder and is an alcoholic, but for now is on antidepressants and is controlling his drinking. This kid has a job and is buying a car and has been told that, as of January 2020, he will need to move out because the house will be on the market. And his kid says he is fine with that.
So the question is: I have experience dealing with both an alcoholic relative and a mentally ill relative. (Lucky me!) There is no circumstance under which I would be OK having this adult child live in our house with us. And because I have this experience, I know his kid will be needing a place to stay on occasion, and for an indeterminate amount of time in the next 12 to 1,500 months for the rest of his life. What do I do?
A: Talk to your partner before the two of you move in together and make sure that you’re actually on the same page about this; if you think you’re not, don’t move in together. That’s the simplest part! There’s also the complex aspect of letting your boyfriend’s son be his own person—your experience with your own family members is certainly relevant, but everyone’s experience with addiction and mental illness is at least a little unique, and it will be possible for you to maintain your own (perfectly reasonable!) boundaries here while also treating this young man like a human being. You say “lucky me” in response to having a mentally ill relative and an alcoholic one—without diminishing the pain and frustration you may have experienced in your relationship with them, I would argue that this is not something either of them did to you, and that your “luck” doesn’t really enter into it.
But the most important thing, I think, is to make your expectations very clear to your partner before you two move in together, and if he’s at all squishy on not living with his son (or even if you’re inclined to suspect his promises to the contrary), then there’s no reason to rush co-habitation.
Q. Re: Silence surrounding long-ago loss: Two months after I was born, my parents’ second child died of childhood cancer. (For reference, I am the fourth child of five, born precisely in the middle of the 10-year difference between the oldest and youngest siblings.) There have never been pictures of him displayed outside of family photo albums, and it’s quite rare that anyone knows there was a fifth child. Much of this was due to my mom’s grief over losing a child, but we never questioned this, nor would there be any reason to have a family discussion with partners of my siblings. It happened decades ago, and it was incredibly difficult for my mom, but she’s also not the type to open up and discuss that kind of loss even with her own kids. Let it go unless a family member brings it up of their own volition.
A: I think that’s the right approach to take with the girlfriend’s family. I can understand wanting to ask her a bit about it (assuming she’s open to it, and that the questions are all fairly open-ended rather than invasive, etc.), but ultimately the answer to this question is basically just: “One of their children died as a baby. The family doesn’t talk about it much.” You’re not going to change this dynamic and it’s not inherently unhealthy; the best-case scenario is you learn a little more about how your girlfriend feels about it, not make any changes yourself.
Q. Resource-constrained friend: I have a very good friend who is having some financial troubles. Actually, they’ve been going on for a while and are likely baked into the cake for the foreseeable future. I go on occasional expensive trips, some of which he’s joined me for in the past. Recently, he confided that his financial troubles are deeper than I realized—as in, not just living paycheck to paycheck but dealing with significant (!) credit card debt. I have an expensive trip coming up, but I don’t want to invite him to join me because I’d feel guilty about him going deeper into debt. I can’t treat him, both because his pride would reject it and also because it would be too much for my budget as well. But if I don’t invite him, I know he’ll be hurt. He’s a grown-up, and he can make his own choices, of course. But still, I don’t want to feel like I am tempting him (or encouraging him) to get deeper into debt, and also if he does come I know I’ll feel constrained to try to limit our expenses, which will mean I won’t get to do things I’d like to do. We do also see each other in less spendy circumstances, so it is not like this is our only opportunity to get together. What should I do?
A: Don’t invite him. You say you don’t invite him on all of these trips, so it’s not as if you’ll be breaking precedent here, and you can’t afford to treat him (and he can’t afford to go). Invite him over for coffee or dinner when you get back, but don’t put yourself (and him) in a situation you know will result in discomfort, unequal expectations, additional debt, or a sense of obligation. Go on your own vacation and have a wonderful time.
Q. Re: Overly intimate acquaintance of social media: The letter writer said this online acquaintance keeps creating new accounts and refollowing her every time she blocks him. That’s stalker behavior. By all means, tell him to knock it off, but keep copies of all of his messages. He’s probably also violating the social media platforms’ terms of service by creating multiple accounts, so report him to Facebook, Instagram, etc. This guy knows he’s behaving badly. He knows you’ve blocked him multiple times, and he continues to find ways around it. Be very careful, especially if you live near each other.
A: Yes, be sure to report each new account, not just block, and gauge what the odds are that you think he’ll try to escalate. Someone else advised not to say anything to him; I’m still on the side of saying, “You need to stop” just once, but I certainly don’t think that you have to.
Q. Lingerer loathing: My roommate and I have an issue we could use your help on. Her friend “Jonathan” moved back to the area last year and his longtime girlfriend broke up with him shortly after, leaving him with few friends here and a broken heart. He reached out to my roommate to reconnect and started coming over to watch shows, go for runs with my roommate, and just generally hang out. During this time, he has become my friend as well.
Our issue is that he is a lingerer! Sometimes he will even fall asleep on our couch. For a while he had a bad living situation and we could not blame him for not wanting to go back to that. But no amount of gently (or not so gently) hinting that it is time for him to go gets him to leave in a timely manner. We can say, “OK, it’s time for me to make dinner/take a shower/go to bed,” and we can physically begin to do these things, and still he will linger for 10-plus minutes. He will start putting his shoes and jacket on, all while slowly moving his way toward the door, trying to keep up a conversation the whole time. Sometimes he will just stay on the couch until we physically start leaving him to head upstairs. My roommate and I are both sympathetic to the fact that he just needs some friends and a place to hang out that he can feel comfortable in, but we are annoyed with this habit of his. We enjoy and value our friendship with Jonathan and do not want him to feel unwelcome at our house. But we need a way to tell him “It is time for you to leave now” that he will actually listen to.
A: Since you’re close friends and you spend a lot of time together, you have a lot of room here. In my experience, once people have reached the “don’t stand upon formality” level of friendship, they respond really well to clear, cheerful announcements to head home at the end of the night. Instead of “OK, it’s time for me to make dinner,” just say, “I’m exhausted! Time for you to clear out. Talk to you tomorrow!” You can say it cheerfully and in a spirit of playfulness so he understands you haven’t suddenly turned on him, but you should say it and stick to it. If you need to hand him his shoes and stand by the door holding it open so he gets a clearer picture of the leaving process, do it, but it’s time to stop assuming he’ll pick up on any hints and start saying exactly what you need: “All right, off the couch; I’m taking a shower and I need you out of here.” “Let’s talk about this later; I don’t have time to get into this right now.” Maybe even “Scoot!” But leave the hints behind you.
Q. Update: Keeping in touch: I’m the letter writer. Receiving your advice has been a gift—both your writing and the comments section. It’s solidified that I’m not going to contact the person in question and that I have plenty of work to do on myself, and that’s where my effort should be going. I think part of my desire to spend time with her (this wasn’t romantic, or violent? That really threw me, as many of the commenters suggested) was because I wanted to help her, because I wanted to help everybody in that program. When I was there, I was the most functional person by factors of magnitude. We did have some pretty rare things in common. I would have approached via social media if she’d had any social media profiles, but she doesn’t, and I should have taken that as a clear sign. I don’t want to make any more of this about her because I should be focusing my energy on coping with my mental illnesses more effectively. Again, thank you and your comment section for the advice.
A: Thank you so much for keeping us posted. I completely understand both the desire to stay in touch with someone who was present during a pretty significant portion of your life and also the impulse to help other people. (Especially since your own time there wasn’t especially productive—my guess is that desire would have made it feel redemptive, like, “Even if it didn’t do much for me, at least it was worth going so I could be useful to others.”) It’s not necessarily a rejection of any kind; she’s just in the middle of a crisis and doesn’t have much time or energy to spare. I’m glad you’re looking after yourself. I hope things only get better from here on out.
Q. Too honest: Before meeting and marrying my wife, I had many different sexual partners, mostly casual. I’m her first. We are in our first year of marriage. During a conversation about our sex life, I mentioned that I had been more attracted to past partners than I am to my wife. She became visibly upset; in the days since, she has stopped initiating intimacy and has asked if I want an open marriage. I said no. I tried explaining that I am attracted to her—it’s just that the physical dimension of our relationship is less important to me than the emotional, intellectual, and spiritual connections we share. And, truth be told, I have had some sexual relationships in the past with an explosive chemistry that my wife and I lack. Did I overstep a boundary? I thought I was just being honest, but my wife is clearly hurt, and I don’t know how to reassure her without lying.
And find even more letters in the Dear Prudie archive.