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Am I Hot or Not?Prudie counsels a woman whose boyfriend doesn't compliment her appearance—and other advice seekers.

Posted Monday, Oct. 5, 2009, at 3:16 PM ET

Emily Yoffe, aka Dear Prudence, is on Washingtonpost.com Mondays at 1 p.m. to chat with readers about their romantic, family, financial, and workplace problems. (Read Prudie's Slate columns here.)

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Emily Yoffe: Good afternoon, everyone. I look forward to your questions.

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Chicago: I'm an attractive (not to sound narcissistic, but you'll understand as I continue) 26-year-old female and have been dating my boyfriend for five years. He never, EVER tells me that I'm attractive. Not in bed, not when we're at weddings, not when we go out on dates. I have talked to him endlessly about it, and he says he thinks it but he just can't say it. Sometimes he'll try, and it's pretty obvious that he's only doing it so he doesn't get yelled at later, but then he'll stop until I have to remind him again. I need to be told that I'm attractive, not because I have low self-esteem, but because it makes me MORE attracted to him. I'm at the point where I don't want to do anything in bed with him because he doesn't make me feel sexy. Plus, it does hurt when I hear him talk about other attractive people (actresses, people we know, random strangers on the street). He also doesn't do the cute things guys do, like send me a cute note about how much he loves me or get me flowers when I'm having a bad day. ... Fine, I watch too many rom-coms, but still, he doesn't do anything out of the ordinary to make me feel special. He seems to be happy with doing pretty much nothing and watching a lot of football. I love him, but I don't know what to do. Is this something I should accept as his personality or a byproduct of being in a long relationship? Am I just overreacting, or is this a relationship deal-breaker and I need to get out?

Emily Yoffe: This sounds like a great relationship! You are constantly yelling at him to tell you how attractive you are; he is constantly zoning out of the relationship to watch sports. You are constantly expecting he'll snap to it like Matthew McConaughey in the final reel. He is constantly disappointing you. Also, you don't like to have sex with him anymore. All this isn't the description of a long relationship. It's the description of a long, lousy relationship. You both sound like you need to move on, but I'm not sure you've each extracted the lessons from this one you should have to make the next one better.

Dear Prudence Videos: Hot-Flashing Boss

Kansas City, Mo.: My sister and I (both in our 50s) bought a house together two years ago so we could share caregiving for our 80-year-old mother. I stipulated that I wouldn't permit my sister's ex-husband to visit the house—he's a lifelong alcoholic and has verbally, mentally, and sexually abused my sister; made sexual advances to both my mother and my other sister; and despises me because I don't take any guff from him. My sister still loves him, still refers to him as her husband (they were divorced 22 years ago), talks to him on the phone every week, and is astonished when the rest of our family refuses to invite Ex to family dinners/holidays. (Yes, I think she desperately needs counseling, but whether she ever gets it or not, I'll still love her.) However, she agreed that Ex would be barred from the house. Sis has two adult sons; the younger one has a restraining order to keep Ex away from his home. My older nephew and his wife also refuse to have Ex at their home. They recently had their first child and made it very clear to Sis and me that they don't want Ex around their baby. Sis, oblivious as always, invited Ex to the hospital to await the baby's birth. My nephew and his wife were livid but chose not to make a scene and weren't brave enough to confront Sis about it. Here's the problem: Sis and I volunteered to provide free baby-sitting on the weekends. Sis just told me that she invited Ex over this weekend to see the baby, because "he hasn't seen her since she was born." I seriously doubt she's cleared this with my nephew and his wife. I realize I'll have to have yet another conversation with her about Mom and I not wanting Ex in the house for our own reasons. But should I warn my nephew and his wife about the invitation? It's up to them to set the boundaries with Sis and Ex, and I can't interfere with that. But they're trusting me with their infant daughter, too, and I don't think Ex should be here unless they say it's OK.

Emily Yoffe: Letters like yours make me think that "family" is overrated as a way to organize society. I will not raise the obvious issue of why you would live with someone who likes to bring an abusive sexual deviant around so you can have the conversation about why you don't want him around on an endless loop. That said, yes, you must tell your nephew and his wife about the invitation—they are entitled to know their mother is violating their explicit instructions about caring for their daughter.

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New York: An old college friend of mine calls frequently to agonize over problems I would kill to have. Some recent examples: On her luxury vacation to Bali, should she stay at the resort on the beach or the inland one with the great spa? When she takes six months off next year to write her memoirs, should she do it from her home or go stay at a writer's retreat? Should she get a personal chef, or is the personal trainer enough?

Her wealth is family money—she's spent the nine years that I've known her as a part-time grad student and has never held down a full-time job.

She is a sweet, caring friend. But my jealousy (combined with irritation over her lack of self awareness) is making it really hard for me to interact with her. I haven't returned her calls in two weeks.

I don't want to end this friendship, but I also don't want to spend 70 percent of it resenting her good fortune. Help.

Emily Yoffe: She is a sweet, caring, spoiled, and oblivious friend. Traits that weren't so grating in college grate more now, and you are free to move her to a more peripheral friendship status. As for the problems she presents you with, just be more blunt. "Cynthia, it's wonderful that you have the financial comfort to have to wrestle with such issues as whether you need your own chef, but I'm afraid this is the kind of dilemma for which I have no insight." But with problems like this, I'm sure her memoir will be gripping. What's the title, "Trust Fund Baby"?