Dear Prudence

To Err in Eros

Prudie’s advice on a pilfered necklace, expecting a ring, and flowers for Mom—just in time for Valentine’s Day.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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Dear Prudence,
I dated a man who was separated from his wife (they were both aware of the separation, thankfully). While we were dating, he stayed the night a handful of times. The last time, I noticed that a pearl necklace my father had given me was missing. I turned the house upside down, but never found the necklace. Eventually our relationship fizzled and he reconciled with his wife. Then, a mutual friend forwarded an image his wife sent out of a beautiful pearl necklace he had given her to symbolize their new commitment to each other. This necklace already has sentimental value—to me! The necklace has unique elements, and I have photos of myself wearing it. When I tried to ask the guy about the necklace, he blocked my number. I could contact his wife. I don’t want to squash their reconciliation, but I can’t think of any delicate way to explain the situation and ask for the necklace to be returned. Should I let the necklace go and wish them the best, or should I let her know that her husband is part of the Bling Ring?

—The Bedroom Burglar’s Ex

Dear Ex,
At least this jerk didn’t steal your heart. Your Bling Ring reference makes me think of the classic To Catch a Thief, and I say with certainty that your cat burglar is no Cary Grant. Perhaps this guy said to himself that he wanted a memento of your beautiful affair, and now every time he sees it around his wife’s neck he thinks of you. You should give him another reason to be on his mind. I know Valentine’s Day is upon us, but don’t get so carried away with the idea of romance that you are willing to let this light-fingered guest make a grand gesture to his wife with your jewelry box. Contact his wife (tomorrow would be an appropriate day!) and tell her that while she was on hiatus from her marriage, you and her husband dated. Explain that during this interlude, a pearl necklace given to you by your father disappeared from your house. Say the mystery was solved when a friend forwarded you a picture of the wife wearing it. Acknowledge this is distressing news, but that if she has any doubts you can send her photographic evidence the necklace is yours. Let’s hope that she doesn’t rip it from her neck and throw it in her husband’s face, but instead makes arrangements to return it to you. After all, she now knows the symbol of her husband’s commitment is stolen property. If she decides that instead of returning it, she’ll just also block your number, gather your photographic evidence and have the police visit this pair.


Dear Prudence: Dressing Down

Dear Prudence,
I started dating a great guy about a month ago and I’m at a loss with how to approach Valentine’s Day. We’ve been on four fun and pretty amazing dates so far. I’m scared to bring Valentine’s Day up to him and have him reject me—whether it’s because he’s got plans with another girl (we haven’t had “the talk”), he decides to go out with his friends, or just isn’t invested enough in “us” to do something. He’s a romantic and sweet guy, so I’m sure he’s not oblivious to the fact that Valentine’s Day is coming up. Do I just keep my mouth shut and do my best not to be disappointed if he doesn’t mention V Day or plan anything? Or should I be brave and bring it up in a casual, playful way? Things are progressing very nicely between us and I don’t want this holiday to mess things up.


Dear Fretting,
If you’ve seen this guy four times over the past month you’ve been going out once a week. So I hope this week you two have a lovely Saturday evening and ignore the pressure that Friday’s Valentine’s Day would impose on such a nascent relationship. There’s no hiding from the fact that it’s Valentine’s Day, but since you don’t even know if he’s dating other people, now is not the time to be brave about the year’s most fraught romantic holiday. If by now you don’t have Friday plans with your new guy, then go out with friends, or stay home and watch the Olympics and be grateful you’re seeing things better than Bob Costas. If things continue to progress, you two will have plenty of time to plan a blowout celebration on Feb. 14, 2015.


Dear Prudie,
Up until a few years ago I would send my mother either flowers or some other gift for Valentine’s Day. Then one year, I didn’t give her anything. The reason was partially financial, but also because my then girlfriend (now wife) told me that Valentine’s Day is for couples, not mother and son. My mother took the lack of her acknowledgement as a slight and was very upset. Nevertheless, I have not given my mother anything for Valentine’s Day since. However, every now and then I will come across a blog post, or have a conversation in which someone mentions giving his mother something for Valentine’s Day. So, am I a rotten, ungrateful son? Or is my wife correct?

—Shamed Son

Dear Shamed,
If you’re part of a couple, unless you mutually agree that Valentine’s Day is an oppressive institution, you ignore this holiday at your own peril. Beyond honoring your significant other, everyone has their own style. Some people like to bring in sweets for the entire office. Some people like to spread the love to family members, or even friends who might not otherwise get a card, flowers, or chocolate. You established a lovely custom of acknowledging your mother on Valentine’s Day. This didn’t involve blowing off a date with your girlfriend, now wife, in order to have dinner and go dancing with Mom. What your girlfriend put the kibosh on was but a small token of appreciation. How weirdly jealous and unpleasant of her. I think you should re-establish your tradition and put in a rush order for flowers or chocolates to your mother. I assure you, even if it doesn’t arrive in time, when she gets it she will be delighted. You don’t need your wife’s permission for this. And if she finds out and tries to shame you, tell her you find it a shame she would be so mean and petty.


Dear Prudence,
How do I keep myself from expecting a ring for Valentine’s day? My boyfriend and I are both 26 and we’ve been together more than three years. I’m ready! He’s the one! We’ve talked about how great it’s gonna be! In the summer I asked him about his thoughts on our timeline and told him I was ready. He got uncharacteristically anxious about marriage and wanted to hold off a while. (He’s a law school graduate who hasn’t been able to find work as a lawyer, which doesn’t matter to me.) I agreed we should both be 100 percent ready, but told him I didn’t want to wait another year and he would need to make a decision before then, preferably well before. I haven’t pressured him since then and things have been going great. He’s as much as said that there is a big Valentine’s Day gift coming to me. I sooooooo hope it’s a ring! If it’s not, I want to be able to be reasonable: keep a good poker face for the night, wait a couple weeks so I’m not speaking from a place of disappointment, and again get his thoughts on where he stands as far as being ready. Help me to temper my expectations and not freak out if I don’t get that special thing I want!

—V Day Anxiety

Dear V,
Yours is the flip side of the dilemma faced by “Fretting” in the letter above. You know you’re in a committed relationship and that Valentine’s Day will come with dinner, flowers, and a gift. You just don’t know if the gift will be the diamond you are seeking. Let’s face it, anything else will feel like a lump of coal. If your boyfriend is hinting you’re going to get something that will rock your world and it turns out not to be an engagement ring, then he is terminally oblivious or rather callous. I have written many times that I hate the whole waiting for an engagement ring ritual. It turns powerful, accomplished women into passive vessels hoping to be told the man in their life wants them enough. It’s good that you did forthrightly tell your beloved your desires about your future and then had a conversation about how you each are feeling. So until you get your gift tomorrow night (no rummaging through his sock drawer), you won’t know where he’s at. Practice smiling and saying you love your pearl necklace, if that’s what you end up receiving. I’m betting if it’s not a ring, you won’t be able to wait weeks, or even days, to have that conversation about your future. What you want is fair, and you need to hear if he’s not ready now, or doesn’t know when he will be. If it turns out he’s not the person you’re going to spend your life with, don’t forget how young you are and how much life there is ahead.  


Discuss this column with Emily Yoffe on her Facebook page.

More Dear Prudence Columns

The Only One—Or Else: My girlfriend has a fit whenever I mention my late wife. What should I do?”
My Mother the Identity Thief: My mom has been running up credit-card debt in my name. What do I do?”
Bed Bug: My husband invited a homeless woman to live with us. Should I divorce him?”
Confessions of a Favorite Daughter: My parents’ blatant favoritism made me a narcissist and my sister depressed. Is it too late for me to stop it?”

More Dear Prudence Chat Transcripts

My Life as a Sugar Baby: In a live chat, Prudie advises a woman on whether to stay mum about having dated rich men for money.”
Tongue Oppressor: In a live chat, Prudie advises a woman whose boyfriend obnoxiously licks her face.”
My Creepy Keeper: In a live chat, Prudie advises a woman whose brother-in-law “watches over her” by peeping through her bedroom window.”
Don’t Look, Ma!: In a live chat, Prudie advises a man whose wife refuses to hide a nude print the next time his mother comes over.”

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