Our advice columnists have heard it all over the years—so we’re diving into the Dear Prudence archives to share classic letters with our readers. Submit your own questions to Prudie here.

Dear Prudie,

My boyfriend and I have been together for almost a year and a half now, and I love him dearly. He stays at my house a couple of nights a week, and there have been three separate occasions when he has wet the bed; however, he doesn’t know that I know he wet the bed. I feel bad because I can tell when it happens that he’s terrified and just praying to God that I don’t roll over and realize that the bed is soaked. I just don’t know how to tell him that I know. I don’t want him to ever feel ashamed of it (my brother had this problem when we were growing up), and there is no way I would ever think less of him because of this. How do I broach the subject? I just want him to know it is nothing to be embarrassed about without embarrassing him.

—Sleeping With a Bed-Wetter

Dear Sleeping,

Unless you want to have a recurring dream that you’re in steerage on the Titanic, you have to speak up. One of the loveliest things about intimacy is being accepted despite the least lovely things about us. Although you dread this conversation, ultimately it will relieve him. He probably goes to sleep each time he’s at your place dripping with anxiety that by the morning he will have turned your mattress into a water bed. But since it’s only happened three times in 18 months, the good news is that the overall forecast is for mostly dry conditions. At some relaxed time, just tell him in a low-key way that on a couple of occasions you noticed the bed was wet. Explain you’re very familiar with this issue because your brother experienced it, and you don’t want him to feel uncomfortable if it happens again. Tell him if he hasn’t had a thorough urological exam, he needs one. This website discusses the possible causes of enuresis and describes some techniques and treatments that might be helpful. Being able to be open with each other about this will be a great investment in your relationship; and buying a waterproof mattress pad will be a great investment in the life of your bedding.

—Emily Yoffe

From: Stream of Unconsciousness. (March 5, 2009)

Dear Prudence,

I was riding the subway to visit some pals in a neighboring borough and a pleasant young man got on two stops after I did. He and I chatted about the weather, the stock market, and the Mets. About five minutes into our conversation I noticed a lot of people were looking at him funny. Then I heard muffled chuckles that eventually built up to whooping, bansheelike laughter. When he turned around to find out what was going on, I noticed the problem: His hairpiece had gotten caught in itself and was all askew. I tried to casually tell him the problem, but I too broke up.

Prudence, the look on his face was heartbreaking. And to make things worse, this guy belongs to my gym and I see him often. Every time he sees me a look of pure dread comes over his face and he scampers away. I feel awful. I want to apologize to the guy, but I am afraid that would make him feel worse. Got any ideas?

—Lacking Tact, but Trying

Danny M. Lavery and Emily Yoffe Read More

Dear Lack,

My Wife Is Adamantly Against Allowing Our Daughter to Enjoy a Childhood Rite of Passage. Her Reason Makes No Sense. My Boyfriend Knows My One Big Boundary in Bed. He Went Ahead and Broke It Anyway. Help! We Generously Offered to Take Over Custody of Our Grandson. We’re So Frustrated at How His Parents Responded. My Sisters Have Always Resented My Existence. Suddenly, They’re Changed Women. I Know It’s a Con.

As Prudie read your letter, she too laughed out loud, but here’s a suggestion to put everyone at ease. Since the episode with the screwed up rug has been tacitly acknowledged, and the guy tries to hide from you because of embarrassment, invite him to sit down for a chat or a cup of coffee. If you make the first move and issue the invitation, he will sense you are a safe place, and then you can have a conversation. Tell him he has a very pleasing personality, and why is he bothering with a rug, anyway? Mention some well-known bald guys: Yul Brynner, Sean Connery, Michael Milkin, Kojak … anybody you can think of. Then suggest he give the natural look a try, pointing out that many women find balding men sexy. This chap may or may not give up the rug, but at least you will have tried to ameliorate his embarrassment, and the meeting-greeting relationship at the gym will get back to normal.

—Margo Howard

From: Death Becomes Her. (June 15, 2000). Read about the response to Prudie’s advice here. 

Dear Prudence,

Please settle an ongoing dispute between my husband and me. My husband believes it is OK to floss his teeth while driving his car. (I am not making this up.) His teeth are very nice, but I believe this activity should be restricted to the privacy of the bathroom only. He does not see a problem doing this in public. Please respond.

Sincerely,

Mrs. Floss

Dear Mrs.,

Prudie hesitates to ask what he is steering the car with. Flossing is not a one-handed maneuver. You are correct that it is not an activity meant for public viewing but, more important, seeing to one’s dental hygiene while driving a car poses a threat to oneself, as well as to others. Do tell Mr. Floss that Prudie implores him to find four minutes to do his admirable oral upkeep when he is outside of his automobile.

—M.H.

From: Driving While Flossing. (May 27, 1999)

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