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Posted Monday, April 13, 2009, at 3:40 PM ET

Five months ago, I started dating a friend of the family (his sister is so close to my mom that she was present at my birth, and she often refers to me as 'family,' invites me to Christmas dinner, etc.). We haven't told our families because they're unlikely to approve as he is 15 years older than me; I'm 26, he's 41. We are exclusive, and he's now a big part of my life. I'm beginning to feel like there may be a certain point where the omission of not telling our families (that we're close with) is too big, but I don't know where that point is, exactly. Is it none of their business or should we clear the air? should we wait until we have dated longer (like a year? Or wait until we want to move in together, etc.?)?

Secret Girlfriend

Emily Yoffe: Fifteen years is a big gap, but it's hardly the Grand Canyon of age differences. It sounds as if the time to mention this is now because you are starting to feel funny about not doing so. Since neither of you think anything is wrong, acting as if it is certainly leaves the impression you agree with the people who will disapprove. But you're both adults, so it's one thing to let your families know important news about your lives, but it's another to act as if you're asking your permission. You're not asking permission—you're just letting them know about your happiness.

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South Orange, N.J.: In our world, we have a circle of relatively new friends I'll call "Ys"—we met most of the Ys within the last year or two. All know I'm unemployed, and have offered the usual support ("if I hear anything or know anyone...").

When they ask how my hunt is or how I'm doing, I'm torn about how much detail to give for an answer. I don't run the detail of "sent out 45 resumes, responded to 18 ads each of the last days," but I do give a "highlights"—"second round interview at one company, three other first rounds didn't progress, seems like there are more ads this month than last."

My wife favors more of the "doing well, seen some action" response, which sounds both pitiful and not sharing enough to me.

What are your ideas for us unemployed?

Emily Yoffe: Unless the Ys are in the industry you are looking in and you think having a more in depth discussion with them will improve your job hunt, there's no reason to give a more detailed answer to "How's the job search going?" It's a similar question to "How are you?". Usually you just give a brief, anodyne response in social settings. But with close friends, who truly want to know how the job search is, or how you are, you give more details.

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Back to the basics: Really basic question here. I'm not a phone person. I prefer texting or emailing. However, I've noticed that when I date men, my reluctance to talk on the phone negatively affects our attempts to get to know each other. With that in mind, I've decided I need to at least give it a shot. I'm fine with the brief five minute "how was your day" call, but I'm thinking to give this a fair chance, I probably have to start doing longer phone calls. What is normal? Or is there no normal, and I can continue in my anti-phone ways? I'm in my 30's, so I grew up talking on the phone, and thus have no excuse for my texting ways. Thanks!

Emily Yoffe: From what I see and hear I think the world is beginning to divide into two groups of people. Those who love to shout into the cell phone that there was too much mayo on the turkey sandwich they had for lunch, and those who prefer to text this crucial information. I just read an article that young people are refusing to even listen to their voice mail anymore because it's so cumbersome, and they get annoyed with anyone who won't just leave a text. So you are not alone in your aversion to the drifting nature of the live phone conversation—and I'm surprised your beaux are still stuck on this technology. If they want to talk, however, of course you should make the effort. But even in today's world of instant communication, nothing beats using the phone, or a text, to make a date to actually get together in person as the best way to get to know someone.

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Washington, D.C.: A little over a year ago, I left my husband because of his verbal/emotional abuse. We have a child, and in the years preceding the separation, I had worked full time (as had he) and I had also obtained a post-graduate degree at night. He and I share completely equal custody (despite his verbal/emotional abuse to me, I think he's been a good father—so far). Because I have been unwilling to get into the nitty-gritty of our split with co-workers, mutual friends, and some family members, some people have assumed that I left him because I was done with the post-grad degree, making a good salary and no longer needed his help (I left him a little less than a year after I was done with the post-grad degree).

I am so frustrated at times (the most recent was a digging comment by my 86-year-old grandmother) that I just want to tell everyone WHY I left him—but at the same time, I don't think that's right, nor do I think it's productive. Those who need to know (my mom, brother, and a few close friends) do know. Any recommendations for how to handle the rest of the peanut gallery?

Emily Yoffe: The people who need to know, know. No one wants a dig from Grandma, but isn't she close enough to be told that your ex was an abuser? It's too bad she made a dig, but surely it makes no sense to her that you would walk out of what looks like a good marriage for no discernible reason. As for the rest, you can say something like, "I appreciate your concern, but as painful as this has been, it is for the best." If they keep pressing, firmly reply, "I just don't want to discuss such a private matter. Thanks."

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Out of the office: NOOOO - you need to establish bounderies. His insistance is ridiculous that it basically gives carte blanche.

It's entirely reasonable not to check in/respond for one day. You can let people know you are out of the office via greeting on your voicemail and an autoresponse to e-mail. If he really needs to get hold of you, he can call you on your cell.

Our society has gone crazy expecting instant access to people. There is almost nothing that can't wait 24 hours.

Emily Yoffe: I agree with you about the mania of 24 hour access. But the letter writer has an overbearing boss, so it's important to pick your fights. As you say, it's not unreasonable to check in once during the day, so do that. That puts you in a better position to distinguish between reasonable and unreasonable requests. Refusing to check in just gives the boss ammunition to say you ignore reasonable requests and you're unavailable at crucial times.

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Arlington, Va.: To the person with the micro-managing boss: it's actually quite normal to check into the office at least once a day when you'll be out of the office. That's just normal in my office. How long does it take to check messages? A minute or two at the most? This really isn't a battle that you want to fight. If your boss is asking you to do it, do it.