Dear Prudence

A Minor Flaw

I’m dating a man who was charged with soliciting a teen for sex; I wish I’d never discovered this!

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Dear Prudence,
Several months ago, I met a nice man at a gathering of friends. We hit it off and started dating. He’s smart, funny, and sweet. He clearly adores me, and I’m starting to feel the same about him. We are both well over 40 years old. On a whim, I Googled his name and found a news article, with a photo of him, describing his arrest several years ago on a charge of soliciting a young teenage girl over the Internet for sex. There was no mention of the outcome of the case, and he’s not listed on a sex offender registry anywhere. He is divorced and his son lives with his mother. I have no children. The physical part of the relationship has been great, and he seems extremely happy to be with nonteenage me. Do I bring this up or keep it in the past, where he seems to want it? Should I out him to our friends, none of whom have young children? How do I (or should I) unlearn what I found out about this otherwise wonderful man?

—Sometimes I Wish the Computer Was Never Invented

Dear Sometimes,
I bet your boyfriend sometimes wishes the Web was never invented, too; then it wouldn’t have been so easy for him to follow his desires to have sex with an underage girl and find himself nabbed by the authorities. You’ve been dating a man you really enjoy for only a few months. Now you’ve found out something terrible about him that he hasn’t told you about, something that’s possibly fatal to the relationship. Think about what you’ve written: You can’t seriously be considering trying to mentally deep-six the knowledge that he was arrested for seeking sex with a minor. You can’t unlearn what you know, and you must learn what you don’t know. He hasn’t been straight with you, but you should be with him. Say: “I found out about your arrest. I Googled your name for fun and saw an article. I’d like you to tell me the whole story.” Then let him explain, and note his demeanor. Is he defensive and evasive? Direct and relieved? (I’m assuming there is something to the charges and his arrest wasn’t a horrible error—and if he says it was all a mistake, get confirmation.) If after hearing him out, you feel you can continue the relationship, tell him your peace of mind requires seeing the court record and speaking to the prosecutor. He should understand this, particularly in light of his not volunteering that part of his past. As for whether you should tell your friends, you can’t decide what they should know until you learn the facts. Your Humbert Humbert may be “wonderful,” but this is too big an “otherwise” to leave unexplored.


Dear Prudence: TMI Divorce Drama

Dear Prudence,
My husband and I met in college in an English class, and our first date was mostly a conversation about our favorite novels. One of my all-time favorite works is Lolita by Vladimir Nabokov. I’m pregnant with my first child, and I want to name our daughter (it’s a girl!) Lolita. However, I’m worried that all the ties the name has with pornography and child molestation may outweigh the beauty of the name and significance the book has had in my life. My husband is ambivalent regarding the idea. What should we do?

Lolita Lover

Dear Lover,
It may be wonderful for your daughter, a couple of decades from now, for her literate (and I hope age-appropriate) lover to whisper, “Lolita, light of my life, fire of my loins. My sin, my soul. Lo-lee-ta.” But it will be less fun for her to have well-read adults do a double-take when she’s introduced or to hear the taunts when her high-school classmates get clued in and start quoting Nabokov. In the years immediately following the 1958 U.S. publication of this scandalous best-seller, the name Lolita had a small but sharp peak of popularity. Then parents must have realized they were naming their sweet little darlings after a pedophile’s object of desire, and Lolita precipitously dropped off the charts, never to return. It’s true that the memoir Reading Lolita in Tehran has given the name an air of freedom against tyranny. But not enough to overcome the sexual connotations. If you went with Lolita, your daughter would be unique in a sea of Sophias and Emmas, but I’m not sure in the long run she’d thank you for it. You and your husband should go through the canon of books that brought you together and find a female character with a less problematic story. If you want to tip your hat to Nabokov, Vera, his wife and creative partner, might be a good alternative. But if you can’t let go of Lolita, make it your little one’s middle name.


Dear Prudie,
After four years of dating and numerous discussions about marriage, I recently decided to propose to my girlfriend. I wanted to get her parents’ blessing first. While my girlfriend was in our bathroom showering, I searched her phone for her parents’ number. She unexpectedly came out of the bathroom and caught me. My befuddled attempt to proffer a cover-up story was met by relentless, vicious accusations of spying. So I apologized profusely and declared my true objective in pursuing her contact list. But nothing I did mollified her outrage, including showing her the ring. Ultimately, she accepted my proposal, but remains incensed that I “invaded her privacy” and has warned it will take a long time until she can trust me again. I acknowledge I could have obtained her parents’ number in a less surreptitious way. But am I totally off-base in thinking that intent is what really matters? I’m concerned that her unwillingness to forgive my mistake is a huge red flag and that my next phone call should be to a moving company.


Dear Befuddled,
Let’s file this jointly under the law of unintended consequences and no good deed goes unpunished. You understand that catching your lover red-handed scrolling through your phone would be disconcerting. Even so, what’s with the “relentless, vicious” accusations? A simple, “What are you doing?” would have sufficed. Once she found out your true mission, that should have immediately changed the tone of your confrontation. (Her overreaction does raise the possibility that she has something to hide.) From your description, it sounds as if you’re living with the twin sister of Susie Essman’s suspicious, foul-mouthed character on Curb Your Enthusiasm. How lovely that she finally accepted your proposal. What did she say: “OK, I’ll marry you, you snooping jerk, but don’t you think I’m going to forget the phone thing anytime soon. And what’s with getting my parents’ blessing? You think you’re a character in a Jane Austen novel? We live together, for God’s sake. Also, the ring is totally not my style.” (I do think informing the parents first is silly, but all your transgressions are misdemeanors.) Now you’re in engagement purgatory, trying to re-earn her trust as you embark on endless conflicts over the wedding. I don’t think you should call the movers just yet. But you need to start some discussions in which you say you feel your punishment does not fit your crime, and you’re worried about how unhappy you both are at the start of what should be a joyous new phase of your lives.


Dear Prudence,
I’m finishing graduate school next year, and last semester I worked part time in a bookstore with an incredible team of people. Unfortunately, the entire company is about to be liquidated. Most of my co-workers were college students, but the managers are soon going to be unemployed. (One has three kids in college.) I really want to send some grocery store gift cards or something, but if I get them for everyone I can only afford $10 cards, and I don’t know how the gift would be taken. I learned so much from this great group of people, and I’m heartsick about their situation. How can I help my friends and former colleagues the most?

—Brokenhearted Former Bookseller

Dear Brokenhearted,
It’s sweet of you to want to send gift cards, but the best, most helpful thing you can do for your laid-off friends is to keep in touch. I’m assuming you were working at the now-shuttering Borders, so that means your fellow booksellers are joining about 10,000 of their co-workers on the unemployment rolls in the worst job market in decades. I heard from re-employed people for this story, and repeatedly they said that while they were out of work one of the hardest things was to keep themselves from becoming depressed recluses. Many who found jobs reported their path back was through a tip from a friend or acquaintance. Make your good deed organizing quarterly get-togethers at a coffeehouse with your core group so everyone can simply socialize and feel like normal humans again, and also exchange tips and leads. Since you’re at a university, keep track of job listings there and forward appropriate ones to your former colleagues. And I hope that when you hit the job market, the economy is finally crawling out of this hole.


More Dear Prudence Columns

Financial Affairs: I want to bequeath money to my mistress in my will. Is that wrong?” Posted March 24, 2011.
A Fool for Love: My wife is super hot but dumb. How can I make the best of our union?” Posted March 17, 2011.
I Can’t Relate: My estranged half-sister wants to get to know me, but I’m afraid my parents won’t approve.” Posted March 10, 2011.
Diamonds Aren’t a Girl’s Best Friend: My ex is blackmailing me for sex. How can I get out of it?” Posted March 3, 2011.

More Dear Prudence Chat Transcripts

This Baby Shower Is a Wash: Dear Prudence advises a reader who thinks her brother impregnated his girlfriend to steal her own baby’s thunder—in a live chat at” Posted March 21, 2011.
Teacher Gone Wild: Dear Prudence advises a schoolteacher caught on tape acting a drunken fool—in a live chat at” Posted March 14, 2011.
Dead Letters at the Office: Prudie counsels an office worker who found love letters while cleaning out the desk of a recently deceased colleague that are not from her widower—and other advice-seekers.” Posted March 7, 2011.
Nightmare Vacation: Prudie counsels a reader who regrets her promise to take an ailing family member to Disneyland—in this week’s live chat.” Posted Feb. 28, 2011.

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