Dear Prudence answers readers' questions live at Washingtonpost.com.

Real-time discussions with Slate writers.
Jan. 11 2010 2:35 PM

Grandma's Prison Pen Pal

Prudie offers advice on what to do when an elderly relative is looking for love in all the wrong places—and other dilemmas.

Emily Yoffe, aka Dear Prudence, is on Washingtonpost.com weekly to chat with readers about their romantic, family, financial, and workplace problems. A transcript of this week's chat is below. (Read Prudie's Slate columns here.)

Emily Yoffe: Good afternoon, everyone. It's hard to get used to writing "2010" on the checks, isn't it?

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Alma, Ark.: My 75-year-old grandma has been widowed for more than 10 years. Most of our family doesn't include her in any outside activities, so she lives a lonely existence. She still works part time outside her home, lives alone, and is healthy. She has been writing to a prison pen pal for almost four years now. She also regularly drives three hours each way to visit this man in prison. She recently told me she and this man, let's call him "Steve," are planning on getting married at the end of this month. Steve is 37 years old and won't get out of prison for six more years. I truly believe my grandma loves Steve and that he makes her happy, but I also know that the rest of my family will disown her if she does this. Should I be happy for her or not? What should I do? Please help. I love my Grandma and want her to be happy, but I don't want her to be hurt by the rest of the family either.

Emily Yoffe: I wonder which came first, your grandmother's estrangement from her family, or Steve? If your 75-year-old grandmother plans to marry a 37-year-old convict, I think the family would do well to try to have some kind of intervention and at least see if Grandma is suffering from a medical or mental condition. What you can do is maintain a loving relationship with your grandmother. Does she have interests besides prison reform that you two could share? Maybe she could tell you some of her memories of her childhood, and you can put them in book form for her. If she brings up Steve, feel free to tell her the truth: that you want her to be happy, but you think marriage to a convict young enough to be her son is not the path to follow.

Danbury: I'll be getting married this October. My fiancee's maid of honor is getting married two weeks before us. She is putting off searching for her own wedding dress because she is insisting that she will lose 60(!) pounds before this September. Both my fiancee and I think this is an unrealistic expectation (she's done nothing to change her lifestyle so far), and it creates a problem with the bridesmaid dresses for our wedding. My fiancee wants her friends to order their dresses by February. How can she politely tell her maid of honor to order a dress in a reasonable size, rather than an idealized one that will probably be way too small?

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Emily Yoffe: She should say that what makes the most sense is to buy a dress that fits now and that if the bridesmaid has changed dress sizes as the fall approaches, there will be plenty of time to get the dress altered. If the bridesmaid insists she'd rather alter herself, then the bride should let it go. Somehow or another, the maid of honor will have something to wear on the wedding day. And if it's something ridiculous, it will be a good story to tell in the years to come.

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New York, N.Y.: I am about to earn my doctorate! This process has taken me six years of graduate school in addition to four years of college. I am still struggling to finish the last chapter of my dissertation in order to meet the deadline to graduate this May. This is not the problem. The problem is my mother. Six months ago, she and my best friend were jointly planning a birthday party for me (with my knowledge) while I was out of the country. The day before my birthday, I received frantic phone calls from both of them, telling me their side of "the story" (they had a huge disagreement that resulted in hurt feelings on both sides and the party being called off).

It is now six months later, and in a recent conversation about my graduation, I mentioned to my mother that my best friend will (hopefully—if she can get time off from work) be there and sharing the large house I will be renting for those who come to attend my graduation. (My friends and family do not live on the mainland U.S., and I have long envisioned having everyone together under one roof as we celebrate the graduation festivities with barbeques, etc.) My mother refuses to stay in the house if Best Friend is there. I wrote her, explaining that this event would be about me and my accomplishments, and not their argument/power struggle. (Incidentally, Best Friend, who is my age, is over this "fight.") In her most recent e-mail, my mother seems to be threatening not to attend graduation at all, as I have "chosen" Best Friend over her. What to do? I have told her I won't choose and will instead invite everyone who has helped me achieve this life goal, but she seems unwilling to budge.

Emily Yoffe: Congratulations on your accomplishment. Since you heard both sides of the story of the fight, and your best friend is still your best friend, you sound smart not to be mediating whatever happened. I often get letters from people marking a milestone who have to contend with family members who say, "If X is invited, I won't be coming." Unless there truly is a good reason someone can't be in the room with X (sexual assault, for example), I think the best approach is to say, "I know you don't get along with X, but it would mean the world to me to have you at my graduation/wedding/etc. X has been invited, so I hope you can put your disagreements aside for this one day. If you can't, I will truly miss you."

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Vienna, Va.: I am unsure how to respond to a woman in my neighborhood who cannot control her large, aggressive Doberman. The dog lunges, snarls, and barks at anyone within 20 feet—the dog often blocks paths and crossings because there's no safe way to pass. The woman will yell at the dog and jerk the leash, but with no result. When I encounter them, I basically have to stop walking until the woman hauls the dog out of sight. The woman is short and slight, and the dog is going to pull her off her feet one of these days. I feel strongly that she needs to either train her dog or keep it off the street. Is there anything I can say or do?

Emily Yoffe: You should ask to have a conversation with her, sans Doberman, and explain that when you encounter her and her dog, you feel threatened by the dog's aggression and how large and strong he is in comparison to her. Suggest that she needs to get dog training classes, because he is a potential hazard if he ever knocks her off her feet. Then if things don't improve, report her to the local animal control authorities. Explain the dog hasn't bitten anyone yet, but the owner needs an official visit because an unfortunate incident seems like just a matter of time.

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Bay Area: This may be more of an etiquette question. ... I wasn't into someone I went out with twice and I am getting e-mails/texts from them. How do I say "I'm not that into you" without being unnecessarily harsh? Since it's been just two dates, one set of friends says ignore the messages and they'll get the hit; another says don't respond till days later and they'll get the hint. I would like a happy medium between being that passive and being too assertive for me, such as "It was great meeting you, but please never contact me again. Thanks."

Emily Yoffe: You did go out with "them" twice, so even though "them" is into you, and you're not into "them," you owe "them" the courtesy of an explanation: "I really enjoyed meeting you, but we just didn't click romantically. I wish you the best."

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Oregon: My brother and his daughter have a volatile relationship. She recently had a baby girl and has cut off all communication with her heartbroken dad. She says he is too controlling and critical. I love them both (they are both wonderful people) and feel torn about what to do. They just don't seem willing to listen to each other. I don't want to take sides, and I don't want them to get upset with me while I try to stay neutral. Is there anything I can say to them that will keep me out of the turmoil?

Emily Yoffe: Your niece just had a baby (is she on her own?) and so needs support. Go and see her and do helpful auntie things with her, and for the time being stay away from the topic of her father. You can, however, report how she's doing to her father; say you are trying to help her in a difficult time and that you hope eventually you will be able to persuade her to resume contact.

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"Writing '2010' on the checks": What's a "check," grandma? Don't you pay your bills online?

Emily Yoffe: You mean that Interwebs thing the young folks keep talking about? I'm too busy crocheting antimacassars to get into that.

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New York, N.Y.: I am a 19-year-old from New York who has a brother in his 30s, and we share the same father. He has lived in Pennsylvania for about seven years. He is married and now has two girls, 7 and 4. Throughout that time, I have only seen him about once, and that was for a funeral. I also have never met my nieces. He recently called over the holiday season and asked me to come visit him, as well as reminding me that I have nieces that I have never met. I have mixed feelings about going to visit him because I do not share the same relationship with him like I do with my other siblings. On one hand, I would love to go visit him and his family. But on the other hand, I don't because we went this long without seeing each other, so why start now? But for some reason I feel so guilty for not going to meet my nieces. And for me, it has been out of sight, out of mind. Now I don't know what to do. Should I visit or not?

Emily Yoffe: I'm going to infer from the letter that your father started a second family that perhaps has gotten a great deal more time and attention than the child or children of his first family. But now that your half-brother has children of his own, he's feeling that he wants to connect more fully to his missing parts, both for himself and his children. It's usually difficult and awkward to start a new family relationship between long-estranged members, but you're not far away, and it seems worth it to at least make a gesture toward reconnecting this lost brother with the rest of you.

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Boston: Is it OK to stay married to one's spouse "for the sake of the children"? My spouse of almost 20 years and I (we're both professionals) have a comfortable lifestyle, but spouse exhibits extremely controlling behavior—tells me what I should or shouldn't eat, drink, wear, etc., and demands constant attention. Constantly calls me at work, calls to check on me—almost hourly—when I'm doing errands in the car. Calls me when I'm on a weekend away with college friends, etc. I've never given Spouse any reason to doubt me or my fidelity. Spouse refuses to join me in counseling (with clergy or professional), even though I've suggested it many times. Spouse can't admit that spouse has control issue. If it were just I and spouse, I'd be long gone.

However, we have two wonderful, smart teenage kids. Both Spouse and I adore them and don't want to see them hurt. However, our kids are savvy enough to recognize Spouse's controlling behavior—they should, because they are on the receiving end of it as well. Spouse is strong-willed and simply won't recognize the problem. We (kids and I) are feeling suffocated.

The younger child is still five years away from college and leaving home. I've pretty much decided to stick it out until this happens—I'll be just 50 years old. Should I gut it out or upset the apple cart sooner?

Emily Yoffe: What's with the pronouns, or lack of them today? First someone was dating "them," now it's you and "Spouse." Living with your spouse sounds intolerable. I wonder if it's always been that way, or if Spouse's behavior has escalated over the years. Since Spouse won't join you for counseling, you need to tell him, I mean Spouse, that you are going by yourself to help you clarify your situation. Explain that you've reached a breaking point with the constant monitoring, dictating, and distrust, and your marriage is falling apart. Say you are reluctant to break up your family, but you no longer can live under the current conditions, and it's Spouse's choice whether or not to recognize what's wrong and try to address it.

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Re: 2010: Who still writes checks?

Emily Yoffe: This morning, a man from the heating company came to fix my furnace. He didn't want to be paid with cookies.

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Chicago, Ill.:

I recently signed up for an online dating site. I have never really dated before, but at 27, I figured it was about time. I met one person from the site about a month ago, and it went well. We have been talking ever since, though his schedule never allowed for a follow-up meeting. This last weekend, I met another guy, and it also went well. We had a nice lunch and talked for a few hours. I don't know if I am still ready for a relationship and liked talking to both of these guys. Am I off base to want to try to develop friendships with these men? And should I tell the other what I am doing? I just have never been in such a situation.

Emily Yoffe: Trying to develop a friendship with agreeable people of the opposite sex you meet on a dating service seems like an excellent way to go. However, your obligation to someone you dated once and whose schedule has prevented you from getting together again adds up to zero.

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Raleigh, N.C.: I'm in a quandary. I recently hosted a casual dinner party with friends. We didn't invite our friend "John" because his significant other is a vegan, and, quite frankly, working around her dietary restrictions was too much of a hassle. (As a side note: the significant other is not generally well-liked among our circle of friends, but that's not the reason we excluded the couple from this particular dinner.) Now John has found out about the dinner party and is upset. Should I explain to him why they weren't invited to this particular dinner? I plan to have them over another time, when I have more energy to devote to planning a menu that accommodates a vegan. Is he wrong to be upset about this?

Emily Yoffe: Since you're having dinner parties and have significant others, I assume all of you are not in junior high school. Because once you get past junior high, you realize that people are entitled to have social events that don't include you. You owe John no explanation. If he brings it up again, just say you look forward to getting together with him another time.

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Re: Controlling Spouse: I am in a similar situation with a controlling partner. Unfortunately, we just purchased a home, and it would be cruel for me to cut and run and leave said partner with a lot of bills (although I would really love to).

Emily Yoffe: You get involved with this person, then, realizing you were miserable, decided a good thing to do would be to buy a house together. You may feel trapped, but you need to figure out why you want to be trapped.

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RE: Controlling Spouse/Kids: As an adult who grew up in this type of situation, PLEASE get your kids out of it. The chat is almost over, so I don't have time to go into details; please just take my first-hand experience as one opinion as you decide.

Emily Yoffe: Good point. The spouse in this situation is creating a pretty unhappy childhood for the children. There's no good solution here. Divorce is awful; so is being hectored and under constant surveillance.

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Grandma's Prison Romance: I would add that you make sure her affairs are in order. I used to be in the elder-law business, and I can't tell you how many times we had to clean up the mess wrought by the elderly person's young "boyfriend." I'm pretty sure it's a common con—romance the older person, and next thing you know, you're in the will and they're writing you $200 checks every day. I'm not saying that's specifically what's happening here—it may be a real love match—but keep an eye on her finances and make sure this guy isn't planning on using her as an ATM.

Emily Yoffe: Good point. Grandma could end up seriously broke and having to turn to the family that has rejected her. As for the possibility of it being a real love match; that seems as likely as the underpants bomber just wanting to make Christmas memorable for everyone on board his flight.

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Wichita, Kan.: I am a 28-year-old woman. I have a master's degree, a good job, and am self-sufficient, intelligent, and attractive. I also have three children, one of which was born when I was 17.

My problem is with dating. I would like to date, and I have time to date some when the noncustodial parent has the children. But I find that the sorts of men I would date will not even consider dating me. I take care of myself and my children. I have a job, a home, and a car. Why won't men who have the same going for them date me? Am I doomed to be alone forever? Should I lower my standards?

Emily Yoffe: You obviously have many sterling qualities, but to a man in his 20s, the matter of three young children is not just an asterisk but a flashing neon sign. Most young single men are going to have second thoughts about getting involved with a woman with so many little ones underfoot. You might do better looking for dates with men who have children of their own. Yes, that complicates one's dating life, but they at least will understand what it means to come as a package deal.

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Raleigh: I purchased an adorable baby outfit for my friend, who is expecting, and she yelled at me for not buying off the registry. I guess I have two questions: 1) Are baby registries acceptable now? I have never liked them, and 2) I am justified in saying it's not appropriate to yell at someone for not purchasing off the baby registry?

Emily Yoffe: The generous thing to do would be to write off your friend's behavior to hormones, nerves, and stress. However, I fear she's just a jerk who will find motherhood most instructive as far as getting other people to do exactly what she wants. Baby registries are fine. Also equally fine is choosing a lovely, unexpected gift. Not fine is yelling at someone who wishes to celebrate your good fortune. Apologies are in order; let's hope she delivers one.

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Emily Yoffe: Thank you, everyone. Talk to you next week.