Dear Prudence

The Littlest Member

My tiny package is wrecking my love life.

Emily Yoffe.
Emily Yoffe

Photograph by Teresa Castracane

Get Dear Prudence delivered to your inbox each week; click here to sign up. Please send your questions for publication to (Questions may be edited.)

Got a burning question for Prudie? She’ll be online at to chat with readers each Monday at noon. Submit your questions and comments here before or during the live discussion.

Dear Prudence,
I’m a single guy in my late 20s with a steady job and lots of good boyfriend qualities. I’m at the point in my life where I’d like to settle down and maybe start a family. The problem is that I have had a horrible time with women, and it pretty much always comes back to the same problem: I have a very small penis. I have a condition called micropenis, and it has been the cause of the end of a few relationships. One of my ex-girlfriends couldn’t stop giggling and said, “Aww, it’s so cute!” the first time she saw it. I’ve had several relationships fizzle out immediately after we start getting intimate. I’m starting to get desperate. I can’t wait around forever to find a mate who’s willing to accept me, and I don’t want to trap a woman in an unhappy and unfulfilling marriage where she ends up sneaking around on me. My sex life hasn’t been all that pleasurable because there’s so much embarrassment and my partner never enjoys it. I’ve thought about posting personal ads that mention it upfront and asking for a one-sided open relationship. I would be monogamous but my partner would have my blessing to have an occasional lover on the side. I have a feeling I’ll probably have to settle for something like this regardless—either behind my back or with my knowledge. Do you think this is a realistic idea, or would I be just setting myself up to get hurt and manipulated? Should I continue to play the field and hope to find a woman who’ll accept my shortcomings (pun intended)?


Dear Lonely,
You deserve a partner who is fully committed to you. I bet you do have many good boyfriend qualities, and among them are a sense of humor and forthrightness. Don’t settle for a situation in which if your wife says she’s working late you’ll be torn up as to whether she’s seeing the boyfriend you tacitly approved. Physically, you’re not a typical guy. So I think you should expand your horizons by looking for a gem of a woman who herself may not be typical. Read this article about dating websites for people with disabilities, including Dating4Disabled. There are plenty of women for whom intercourse may not be the primary way of expressing their sexuality but who want a physical connection and would be great and faithful romantic partners. You need to find someone who is eager to explore all the creative ways there are to sexually satisfy each other. If you meet a woman on a website at which people are upfront about their physical capacities, you would be starting off with someone who is aware of and comfortable with your situation from the start. Think of what a relief it would be to get to know a woman without worrying about the “there’s something I need to tell you” conversation. A targeted search for a compatible partner should spare you unnecessary anxiety and humiliation. I hope the happy ending to your quest is that two people who weren’t sure they’d ever find anyone have found each other.


Dear Prudence: G-String Hobbyist

Dear Prudence,
Until recently I worked at a copy shop, and as I copied, I often couldn’t help but read some of the documents. About a month ago, I had a job that required the copying of emails between a private tutor of young teenagers and a friend of his. Many exchanges centered around very detailed fantasies the tutor had about specific girls he taught, describing their bodies lasciviously and even singling some out by name. He described a time he called the girl’s house just to talk to her and expressed concern to his friend that her mother was suspicious. He wrote graphically about how he wished both he and his correspondent could take the virginity of a 15-year-old student. The two of them exchanged recommendations for adult websites that feature simulations of such events. I told my girlfriend about this, and she thought I should report this guy. But I’m not sure he’s actually done anything, and I’m concerned about privacy violations given how I came across this correspondence. I was worried enough to secretly scan all of the emails and save a copy. Should I mind my own business, or should I forward them on to a state agency?

—Copy That

Dear Copy,
I seriously doubt this tutor is writing a homage to Lolita in the form of an epistolary novel, so I agree with your girlfriend that you should turn him in. If you were a computer technician called in to clear a virus and found evidence of child pornography, in some states you would be required to report this to the authorities. What you’ve stumbled upon falls into a similar category, and we should all be grateful that some sexual deviants are so stupid that they present evidence of their behavior to alert service people. Don’t worry about the privacy of the emails you were asked to copy—in the course of your duties you discovered serious discussions of sexual contact with minors. You even have evidence that this guy is grooming the girl whose home he called. His fantasies don’t sound like idle ones, especially given his line of work. So he needs to get on the radar of the authorities. I suggest you call the police and ask where you would send evidence of a possible sexual predator. Once you find out whom to direct your cache to, you can send it all with an anonymous cover letter, if that’s what you prefer, giving the name of the customer and explaining how you came upon this material. Let’s hope this starts to process of seeing that the tutor finds another line of work.  


Dear Prudence,
My husband’s parents moved across the country to help us with our infant so I could finish my doctorate. They are very adventurous and loving grandparents. We have always gotten along so well my husband jokes that they like me more than they like him. So I am bewildered that now that they are here, I prefer the care provided by our chilled-out baby sitter whom we found on the Internet. My in-laws make such a project out of having “quality time” with our 6-month-old that they constantly keep him on the go: driving on the highway to get to four different parks, going to afternoon classes, and skipping naps. He comes home with a soaking wet cloth diaper and has trouble going to bed at night because he’s so wound up. My in-laws say it’s important to keep a baby engaged, and I admit part of me is jealous that they get to have fun with him while I am doing schoolwork, pumping, and washing diapers. But I want my son to be allowed to nap, I want to know where he is, and I want his diaper to get changed. Is it abhorrently ungrateful that I prefer hired help to my in-laws?

—Tired Mommy

Dear Tired,
First of all, find some other ways to save the planet and switch to disposable diapers. Your in-laws will be more likely to change a disposable, and you can stop washing slop buckets of these rank things. As for your reaction to your in-laws, I think it’s reasonable. Unless there is a medical issue that’s being addressed, a 6-month-old doesn’t need classes. He is already an expert in how to be a baby. Nor does he need to spend a lot of time on the highway in order to find the most invigorating outdoor experience. A walk around the block or time on a blanket on the floor learning to roll over or shake a rattle is plenty of stimulation. What’s not good for an infant is not getting enough sleep and having a soaked bottom. It’s natural for you to not only want to know where your baby is but to have him be nearby. When you hand your baby over to his grandparents, it’s not good for anyone if you micromanage, but you’re entitled to set guidelines. I hope your husband will join you in coming up with these, and in a loving way you can explain to the in-laws that you’re both too nervous to have your child taken hither and yon. Say you’d prefer he go to the local park, and staying close will allow him to come home and get the nap time he needs. If you can afford it, keep that baby sitter and tell your in-laws that you want to use them more strategically. Since they are energetic people, they will have plenty to do while they wait for their grandson to get old enough to appreciate their adventures.


Dear Prudence,
I’m an attorney with a mountain of student and credit card debt. Before I got married, I told my wife about this, but thought I owed about $100,000. It turns out to be about $170,000. When I finally added up the total eight months ago and told her, she accused me of lying previously. My job barely pays me enough to cover our monthly expenses, but I’m supposed to be moving up. I continually look for new jobs and am trying to advance in my company, but that takes time. My wife is in her early 30s and is desperate to have kids and buy our own home, but she insists we can’t because of our financial situation. When I have gone to interviews and was not hired, she blamed me for doing something wrong to blow it. A few days ago she found out one of her friends had a couple interviews for a much higher paying job. She became extremely frustrated, insulted my work ethic, and now won’t speak to me. I don’t know what to do. Should I stay in a relationship that is this unsupportive?

—No Pots to Piss in

Dear Pots,
It’s too bad your wife is incapable of procuring one of those high-paying jobs she thinks are so easy to get. Sadly, there are so many young people in your situation—people who wonder if crushing debt will ever allow them to start families or have a normal life. When you told your then-fiancée you were one of those burdened people, the two of you should have looked closely at your finances and started figuring out a long-term plan toward solvency. If that didn’t interest her, she should have walked. Instead, you now have another burden: a punitive spouse who blames you for everything. I hope your health insurance covers couples counseling. Even if it doesn’t, paying for a few sessions will clarify whether you can save a marriage in which you get the silent treatment because someone else got a job. 


Discuss this column with Emily Yoffe on her Facebook page.

More Dear Prudence Columns

A Marriage Hits a Rough Patch: Hubby’s new beard rubs me the wrong way, but he refuses to shave!” Posted Dec. 29, 2011.
Santa Baby: A grownup throws a tantrum over changing Christmas traditions. Plus, Dear Prudence handles your holiday hassles.” Posted Dec. 22, 2011.
Must Love Cats?: My friends are disgusted that I’d give up a beloved kitty for my boyfriend. But he’s severely allergic!” Posted Dec. 15, 2011.
Poor Parental Activity: My husband is leaving me for my 25-year-old daughter.” Posted Dec. 8, 2011.

More Dear Prudence Chat Transcripts

Wife’s Best Friend Is Hubby’s Worst Enemy: In a live chat, Prudie advises a man whose wife’s best buddy is out to “destroy” him.” Posted Jan. 9, 2012.
In Love With the Nanny: In a live chat, Dear Prudence advises a woman whose ex has fallen for their sitter.” Posted Jan. 3, 2012.
Isolated Incident?: Dear Prudence advises a teacher reluctant to report abuse for fear of fracturing a family—during a live chat at” Posted Dec. 19, 2011.
Ring of Ire: Dear Prudence advises a bride who is remarrying but wants to keep wearing her old ring—during a live chat at” Posted Dec. 12, 2011.