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Dear Prudie,
My manager is extremely sensitive, the sort who borders on being self-involved. I can honestly say she's been a very good boss professionally, but personally she is driving me crazy. She and I are friendly, but she's pushing for us to be best friends. I enjoy her company, but want to keep it business-friendly; after all, she does my performance review! If I'm not overly animated and happy to see her, she assumes I'm mad at her. She then asks around about whether or not I'm mad at her and what she did to make me mad. If I see people from the office on the weekends, she'll sniff out all the details (which I do not broadcast), and then ask me about it, informing me about how much she can drink or how late she can stay up or how she would have added to the fun. She cried over not being invited to my birthday party. She does this to many other people, not just me. We all feel the same way but don't want to upset her. But on the other hand, doing constant damage control ("Oh, no, Susie isn't mad at you, really") is exhausting. How do I salvage this situation?

—Keeping My Distance

Dear Keeping,
You and your co-workers are being held hostage emotionally by your boss. I talked to Marty Kurtz, an executive development consultant in New Jersey. He said that while she's clearly stepping over the line and it's not your duty to repair her psychic wounds, there are some things you and your colleague can do to try to draw better boundaries. When she brings up how much she'd like to socialize with you, tell her that while you get a great deal out of working for her and you enjoy her company, since she's your manager, you feel more comfortable separating your work and social lives. When she starts her game of why-is-Susie-mad-at-me, have everyone agree not to play. Simply tell her, "Gee, I don't know anything about this. You'll have to ask Susie directly." Because she is unstable, there's a possibility she could strike out if she isn't feeling stroked, so keep a diary of these interactions. You could also confidentially go to human resources and say that she's in many ways a good boss, and you'd like their advice on how to handle this aspect of her personality—that way, you're both seeking help and establishing a record of this problem. If none of this results in improvement, Kurtz advises trying to enlist several co-workers, and going to her superior, saying that while you respect her professionally, her emotional needs are damaging your whole unit. Finally, if you're driven mad from too many tear-soaked Monday mornings, you could start looking inside, and outside, the company for another job.

—Prudie

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Dear Prudence,
I am a divorced woman in my 40s. I have been seeing a man in his early 50s, whom I love immensely. He is handsome, intelligent and most of the time he treats me like I am the love of his life. He gets me, he laughs at my jokes, and he listens. He is a wonderful lover—physically and emotionally. The problem? He is never, ever wrong. Whenever we fight, I am the one who has to get us past it with an apology. At first I would apologize with tears and remorse because he was so steadfast in his refusal to acknowledge my side. After two years, I realize that I can't possibly be to blame every time! Last night, after he accused me of behaving like a bitch, I offered an obligatory though lame, "I'm sorry." I didn't mean it. But it was either say those two words or start the fight over again. He doesn't realize this is chipping away at my regard for him. He has never had therapy (I've had tons) and he has never been broken up with. I think that has allowed him to legitimize his feelings and negate those of the other person, and that it has worked quite well for him. Is this hopeless? Do I get out now before I begin to hate him, or do I dare suggest that he examine how he behaves in relationships? My gut tells me he would rather let me go than admit his own flaws, and that makes me so sad.

—Tired of Saying I'm Sorry

Dear Tired,
Yes, it's worked out well for him, assuming his goal is to move from relationship to relationship, never making an enduring one. So much of what you have is so good, but, no, it doesn't make up for the fact that you two can't work out disagreements without your being insulted, bullied, and humiliated. Having finally realized that, you know, too, that you won't end up being the love of his life, just the love of 2005–2007. Let go of the idea that he will see the light when you explain why all his relationships have gone wrong. Instead, tell him why you can't go on. Say that as much as you love him, as reciprocal as most of your relationship is, there is nothing reciprocal about the way you two resolve your conflicts. Explain you've been worn down by the need to always apologize to end a fight, that you've stopped meaning it, and you can't do it anymore. I agree that at this point, he would likely rather let you go than figure out another way. But if he wants to try, let a third party help guide the two of you. If he doesn't want that, how many more evenings do you want to spend making fake apologies after being called a bitch?

—Prudie

Dear Prudie,
I volunteer at a church, where I work very closely with a woman I am increasingly attracted to. I serve in different functions, and in almost every one of them, she's the leader. We bounce tremendously off of each other spiritually and get along really well, and we have the same interests and sensibilities about a lot of things. Sometimes when we talk or are around each other, there are these subtle moments of electricity, though at other times, our relationship takes a more professional type of tone (which kills me). She is a marvelous woman, and when I describe what I want in a relationship, I end up describing her. She doesn't know that I'm interested. I wonder if I should broach the subject, and if so, how I might go about it, seeing as she has a little over 10 years on me in age (I'm in my early 20s) and is in a position of authority over me in a lot of areas. Is this just a pipe dream, or do I have a prayer?

—Confused

Dear Confused,
Forget her being in a position of authority over you—if you can't make a romantic connection with someone you meet while volunteering, then the human race is doomed. There's a good chance she feels what you feel, but then goes home telling herself, "Cut it out, he's 10 years younger, he can't possibly be interested." So, let her know you're interested. Next time you're together, ask her if she's free for dinner one night in the coming week. If she asks if you want to discuss church matters, tell her no, you just want to get to know her better. Given that she may feel awkward about your age difference, if she seems hesitant or confused, tell her you've been hoping that the interest you've been feeling toward her is mutual. If she rebuffs you, then accept that you two will connect only on the spiritual plane, and look for someone else to share more earthly delights with.

—Prudie

Dear Prudence,
My fiance and I have lived together for over a year now, so many of the things we would have registered for, we already have. We're considering registering for more practical types of gifts, and offering our friends and family the option of donating money for our honeymoon or other startup expenses (maybe savings toward the house we want to buy in a couple years). I have thought of asking specific friends for certain types of gifts, as well. For example, one friend is a very talented graphic designer, and I might ask her to design my thank-you cards. She is a recent college graduate like me, so I think this would be easier for her financially, and I would consider it a tremendous gift if she's willing. Is this an appropriate request?

—Trying To Be Practical

Dear Trying,
What a great idea to think of your friends as your personal Yellow Pages! If you have one who's a gynecologist, ask her to give you the gift of a premarital pelvic exam. That bartender pal can pour the champagne at the reception. For that writer friend, hand her the list of the gifts you received, and tell her to get to work on the thank-you notes. Or you could think about your wedding as a lovely event to celebrate with your friends, on the beginning of your married life, and stop thinking about how you can get them to provide services for it. As for your graphic designer friend, you could tell her you love her work and ask if you can hire her—at her usual fee—to create your cards.

—Prudie