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."

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