Dear Prudence

Generation Y Me?

My perfectionist boss is a tightwad with praise. Plus, should my parents help pay off my student loans?

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Dear Prudence,
I’m an ambitious recent college graduate. Six months ago, I moved to Washington, D.C., and was lucky enough to land a well-paying job with great career prospects as an assistant at a law firm. The problem is that one of the partners I assist is particularly challenging. She’s intelligent and distinguished, but she is also a perfectionist. She’s an extremely daunting supervisor—especially for a legal neophyte and nonperfectionist like me. I’m functioning in high gear all day long, but I struggle to keep up. What’s worse is that she is heavy on the criticism and light on the positive reinforcement. A simple mistake like forgetting to put the “Northwest” at the end of a Washington, D.C., address in her appointment schedule will set off a string of negative interactions, while a perfectly orchestrated event will maybe muster an e-mail saying “Tks.” Our exchanges often leave me fuming yet stuck without a venue for venting. At what point can I turn to my boss and say, “Hey, I need things to be different around here” without sounding like an ingrate for the great opportunity that I have.

—Deterred in the District

Dear Deterred,
At any point, you can turn to her and say, “I need things to be different around here.” She will likely agree and respond, “Let’s start by having you clear out your desk by noon.” Sure, your job’s daunting, but you have chosen to work in a high-pressure field in which every detail counts. (And if she has an appointment, she doesn’t want to get in a cab without knowing what quadrant of the city she’s headed to.) You may have picked up by now that people don’t get to be top partners at law firms because of their “Don’t worry, that’s close enough” and “Let’s put it off until mañana” attitudes. But it turns out your frustration with your boss is part of common generational miscommunication. Jeffrey Zaslow had a column in the Wall Street Journal describing young workers’ need for and expectation of constant praise, and how some employers are realizing that they’d better be generous with the stroking if they want to retain them. But the essential problem for you is that given your boss’ personality and demands, she doesn’t think “I’m a nonperfectionist” excuses you from doing things perfectly for her. You’ve only been out of school for a few months, so why don’t you think of working for this partner as legal boot camp? It’s going to be tough and sometimes unpleasant, but if you stick with it, you will come away with a set of skills no amount of flattery will provide. And when you get one of her “Tks” messages, realize it’s the equivalent of getting a smile out of a drill sergeant.


Dear Prudence Video: Virtual Teen Romance

Dear Prudie,
I am a 26-year-old just out of college, and I recently started my first full-time position. I have been paying my school loans back on my own since I graduated, but I’m not able to save much month-to-month. My parents are divorced and somewhat low-income. My dad supported me a little through school, and my mom gave me a little money when I needed it. Neither has offered to help pay back my loans, although they both stressed the importance of getting a college education. I want to bring this topic up with them to see if they are willing to help, but I hate talking to them about money, especially because of their financial situations. I’m worried that they will say I should be capable of making the payments since I have this new job. But I really feel that they should offer to assist with these loans. Am I wrong? If not, how do I ask my parents to help?

—Needs Help With Loans

Dear Needs Help,
I don’t want to sound like this is Dump on Millennials Day, but I’m with your parents. I do have a lot of sympathy for young people who come out of college with sometimes crushing debt. But your parents were right to encourage you to get your degree, and it sounds as if they stretched financially to do what they could to help you. But now that you’ve got it and have landed your first big job, they must feel their efforts and yours have been vindicated. You mention that they are both alone and have little income. But think of what happens down the road when they’re retired, or develop health issues, and don’t have any financial cushion because they kept giving to you to make your young life a little easier. It’s actually in your personal interest to keep your parents as solvent as possible—won’t it be you they turn to if they find themselves old and in financial need? Appreciate that even if things are tight now, your parents have done all they could to ensure you have a more prosperous life than theirs.


Dear Prudie,
I have been dating a wonderful young woman for over a year. We just got engaged. She is smart and witty, and I am very much in love with her. The only real issue I have is her constant need to correct, contradict, and one-up me. Usually, her ubiquitous arguments have no bearing on the subject matter or are without any logic or reason. This isn’t about me being right; this is about me not being able to express any sort of opinion or observation about anything without being contradicted. Some days, it’s a real mental beat-down. I’ve talked to her about this before, and I have no doubt she is aware of the problem. I’m starting to think she does it just to further inflate her ego. How can I deal?

—Not Always Wrong

Dear Not Always,
My husband says since he’s gotten used to this, you can, too. But, of course, I think he’s wrong. I suggest several possible approaches: You could develop a dissociative disorder, which would allow you to enter a state in which either your fiancée or yourself ceases to seem real. Or you could say, “I realize I’ve made a terrible mistake. The wedding is off, but I want you to keep the engagement ring.” Or you could tell her, “I love you, you’re smart and witty and wonderful. But I cannot live with your unrelenting put-downs. Either we solve this problem now, or we can’t go on.” Whichever approach you take, it would be worth it to find out why you have decided you should spend the rest of your life with someone who constantly lambastes you.


Dear Prudie,
I recently had breast-enhancement surgery, and there is a noticeable difference. My question is, How do I respond when people make remarks about it? I know that it is an obvious change, and people do notice, but it is not as if I’m flaunting it in revealing tops. How do I respond when someone says, “Wow, you got a boob job!” I find it very rude when mere acquaintances make such comments, as I would not comment if they got dentures!

—Newly Enhanced

Dear Newly,
There’s a Bible verse for every situation, and Psalms 23.5 seems appropriate here. But what a bunch of jugheads your acquaintances are if they feel the need to keep abreast of your personal developments. Don’t get into a tit for tat with them. Just turn away as you say, “Ta ta.”