In a live chat, Prudie advises a woman whose nanny had an affair with her husband.

A: The point is not to ask your stepson to take the Jockeys and leave the La Perla, but to deal with the fact that he has crossed some serious boundaries. Sure, he's a hormonal teen, and you are young and attractive. But yechh! In a low-key, calm way, tell your husband what you found. Encourage him not to hit the roof or be punitive to his son. Say that as mortifying as this all is, he needs to sit down with the boy, explain what was found, and tell him that he knows it's not okay to take his stepmother's private things. Then after that be as normal and welcoming as possible. Acting as if nothing has happened will be a good skill for your stepson to learn.

Q. Boozy Boyfriend?: I've been dating "Adam," who is 10 years older than me (and in his 40s), for about a year. He is a great guy with a very stressful job who always treats me right and wants to make me happy. I feel like he's quite a catch. The problem is that while during the week he is a hard-working, sober man, he gets drunk every Friday and/or Saturday night! EVERY weekend. He drinks almost 10 beers on a Friday and then a bottle of wine plus a few more beers on the next night, although most of the time he drinks excessively only one night of the weekend. He's very good friends with his neighbors, who also drink quite a bit, and most of his friends love to drink. It's almost like a joke, this adoration they all have for beer and wine. It makes me so uncomfortable! I worry that he abuses alcohol and that he is one tragedy away (say, death of a loved one) from being an alcoholic. I don't drink more than two or three cocktails per week, so sometimes I feel like I’m being hypersensitive about it. I tried telling him by asking, "Why do you need to drink so much?" and his reply was, "I didn't even drink that much!" Even though he's a "nice drunk"—not obnoxious or rude or loud—his answer scares the hell out of me! Am I blowing his drinking out of proportion? I love him and I’m starting to think about our future together.

A: He's not one anything away from being an alcoholic, he is an alcoholic. It's not a coincidence or a joke that all his friends have similar proclivities. It's because booze is their guiding principle. If you want your future to involve calls from the police that your husband has been arrest for a DUI, then that future is yours. And if Adam is getting behind the wheel after 10 beers, take away his keys. You would all do all of us a favor by reporting him as an impaired driver to the DMV.

Q. Nannys: I wanted to respond to the mother/wife with the nanny situation. One possible outcome to this horrible situation is that the nanny learned her lesson in the most brutal and devastating of ways and it will not happen again. A friend put herself in a very similar situation and I watched the humiliation, grief, and massive amount of guilt plague her for several years after the wife found out and the relationship came to a screeching and messy halt. She saw what it did to the wife and family, and has never once looked at a married man since, even though she has been working in the same type of environment in which she met the man in the first place. So let's hope that this is the case in this situation. Sometimes the people who do this are looking for something, and it takes a situation like this to shock them into realizing they won't find it in an illicit and immoral relationship.

A: I agree, let's hope this is the case in this situation. Becoming a professional home-wrecker is a nasty line of work.

Q. Telling My Boyfriend About My Late Son: I married in my late teens, had a baby by the time I turned 20, and watched my precious son succumb to leukemia before I turned 23. Soon after our son died, my ex-husband and I divorced. I didn't date for years, but now I'm in my early 30s and have been seeing a wonderful guy for about three months. He's the first man I've trusted enough to tell about my late son. While my boyfriend knows I was married young, I've never discussed my son with him, because it always seemed too soon. Now I think I've waited too long to tell him, because I've never found the right words. My boyfriend has a daughter, and he assumes I've never had kids. I know the time has come to talk to him about my son, but it's such a personal and important subject that I still have no idea what to say. I'm falling for this man, and he for me, so I want to find a way to share this intimate part of my history with him.

A: It is certainly not too late to tell your boyfriend only now about the most painful experience of your life. Get a photograph of your darling boy and when you are alone, at your house or his, take it out and say there's something you want him to know about you. Show him the photo and say in fact, you did have a child, and tell him the story. It's OK if you cry. It's very hard to imagine your not crying. Tell him you rarely open up to people about this because the wound is still so raw. If your guy is as wonderful as you say, he will be moved by your story and by the trust in him it conveys.

Q. Overwhelming Texts, Emails, and Facebook Posts: In the past year, both of my parents have retired. I was, and still am, very excited for them because they've worked so hard throughout their lives and really deserve to live life to its fullest now. There's one problem from my end: Each day, I now receive 15-20 emails and about five texts from them, and my mother "likes" and/or comments on everything I post on Facebook. And the emails and texts are rarely sent just to me—they're blasted out to at least three or more people, so they're not too personal. I liken this to receiving, in pre-Internet time, 15-20 voice mails and five postcards and letters EACH DAY from my parents. I've been dealing with this by getting really irritated in private, and then answering about one in five messages. When I leave voicemails for them, so we can have a more personal catch-up and hopefully decrease the number of messages coming in, sometimes they call back and sometimes they don't. I live about 15 hours away from family, so I can't easily give them more face time. What to do? Do you think it's appropriate to ask them not to include me on the emails and texts? (I can change settings on Facebook if needed.) That if they want to contact me directly, just call? I'm afraid I'll wind up getting multiple phone calls a day from them in that case. What I'd really like is for us to talk/email just once a week to catch up. Does that make me a bad (adult) daughter?

A: Haven't your parents ever heard of golf? These people desperately need a hobby beyond harassing their daughter. Forget hints, have a serious phone conversation with them about email, phone, and Facebook etiquette. Suggest the three of you set a regular time—say Sunday evening—to catch up, and tell them to save up the news of the week for you to hear. You can also say that a few emails a week are fine, but any more than that and you'll have to delete without answering. (You might also want to change your Facebook settings anyway, to remove their temptation.) Then gently steer the conversation to how they can productively use this gift of free time. Say you know the transition to not-working can be disorienting, but they have so much to give to their community. Encourage them to look into volunteer work—think of the foster kids who could use some very attentive surrogate grandparents.

Q. Re: My Stepson Took My Panties, Help!: If I may offer a helpful suggestion, it may be best for the father in this situation to say that he, rather than stepmom, found the underwear. It would certainly make for a much less awkward confrontation, as stepmom could pretend to know nothing about the entire incident.

A: Since I've already suggested another white lie in this chat, I think your idea about a white lie about black lace panties is a good one. Dad can say he was getting the bedroom ready for guests and came upon the stash.

Q. Lost Ring: My mother over a period of decades took all of the diamonds she'd been given—her wedding ring from my late father plus a bundle of others and had them piled onto a platinum setting the size of a brass knuckle. The ring was last appraised at $26,000. For some reason, she felt it necessary to wear it on a trip to Costco. It fell off in the parking lot. She noticed later—too late. The Costco parking lot gets swept every night. $26,000 in a land fill. We can only laugh.