Dear Prudence

Finders Keepers, Cheaters Weepers

I kicked out my terrible ex-boyfriend. Then I found $10,000 in cash that he left behind.

Mallory Ortberg
Mallory Ortberg

Sam Breach

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Dear Prudence,

I just got out of a financial and romantic wreck. My boyfriend moved his mistress into my guest bedroom, telling me she was a co-worker who “needed a place to stay.” During this time, he sideswiped a fence while driving my car (his had stopped running), causing $2,000 in damage. When I found out the truth, I kicked them both out; she stole some clothing and electronics from me before leaving town. My ex refused to pay for the damage to my car and called me last week, accusing me of taking more than $10,000 in cash that his parents had given him to buy a new car. I told him he was out of his mind and hung up.

He also left a lousy old couch at my place and refused to come pick it up. I asked him if he was ever going to haul it away, and he told me to throw it out. While I was pushing it out to the curb, I found an envelope full of cash under one of the cushions. I haven’t told anyone what I found. I heard from mutual friends that my ex now thinks his other girlfriend stole the money. Part of me wants to wait a few months, then use the cash to fix my car and celebrate. I think that would be fair, given the pain and suffering they put me through—and they actually owe me more than that for the food and shelter I was conned into giving them. I really don’t want to have any further contact with him. The only thing giving me pause is that it is technically his parents’ money and they were always kind to me. I used to consider myself a kind and generous person, but all of this has made me very cynical. I can’t tell anyone I know about the money, so I am asking you.


This is the setup to an amazing O. Henry story, or at the very least a mid-career Carrie Underwood music video, but it’s probably a lot less fun when it’s your real life and you have to deal with the prospect of either dealing with your awful ex or feeling guilty whenever you think about his parents. I think the best option is for you to contact his parents directly, tell them that you found the money when you were getting rid of some of his things, and return it to them directly. You can attempt to collect the money your boyfriend owes you either through your insurance company or small claims court, which will take more time and energy than just taking the $2,000 directly out of the envelope you found. Part of me wishes I could tell you to keep the money as payment for services rendered, but (and we both knew this was coming) this isn’t just your ex’s money. It’s his parents’, and I think you would find it hard to live with yourself if you thought of the anguish they might have experienced to think the $10,000 they set aside for their son to buy a replacement car is gone, even if their son is an unmitigated creep and coward.

If nothing else, think of how awful it would feel to lose the moral high ground if your ex ever learned that you’d found his money and took you to court over it. He sounds exactly like the kind of guy who’d do that.

* * *

Dear Prudence,

I’ve been married for 10 years now and for nearly the whole time my birthday has been an afterthought. This past year was the absolute worst: My husband did nothing besides offer me a perfunctory “happy birthday” in the morning. Meanwhile, it’s time for his birthday to roll around and he’s been agonizing over it for a month—what are we going to do, have I taken the day off, blah blah blah. This year I flat out told him he ruined my birthday, so now I’m getting the guilt trip that since I had such a terrible birthday we should just not do anything for his. I just can’t do that. It’s not in my nature to let a birthday pass without recognition, even if it’s something small (as it has sometimes been in past years). How do I reach the point where I have zero expectations for my birthday so I can just enjoy giving again when his rolls around?

—Birthday Resentments

I do not think your goal should be to have zero expectations, in part because your problem stems directly from the habit you’ve gotten into of acting as if you had zero expectations, when in fact your expectations are relatively high. That’s setting yourself up for martyrdom and disappointment—as does saying “you ruined my birthday” rather than “I felt hurt and ignored that you didn’t do anything more than acknowledge my birthday, and next year I’d like you to get me a present or a card or help me plan something fun for us to do together.” It sounds like your husband is matching your attempts at escalation by offering the “Oh, well, let’s just cancel my birthday too, so we can both be miserable together” gambit, which is childish and unnecessary.

That doesn’t mean you have to take the whole day off work every year and throw a big extravagant party, but you two should have an honest conversation about what you would like from one another on your birthdays in order to feel celebrated and loved. And remember too that your husband is not solely responsible for making sure you enjoy your birthday (and vice versa)! If you want to invite a group of friends out to dinner, take initiative and make plans; if you want to do something special like go to a concert or take a brief trip, talk about it beforehand and communicate what you want, rather than hoping your husband will intuit what you’re thinking and getting disappointed when he doesn’t.

* * *

Dear Prudence,

I started a new job two weeks ago. Today, one of the managers came around and asked everyone if they had gotten something for “Susie’s” birthday this Friday. When I asked who Susie was, I was shocked to hear that she was the owner’s 10-year-old daughter! I confirmed with my co-workers that yes, we are expected to buy gifts for our boss’ daughter and that not buying her a gift could put you on bad terms with him. I’m so lost on what to do—I haven’t even gotten my first paycheck, and I’m being asked to buy a little girl a birthday present! I could afford it with some of my savings, but I’m apprehensive about buying something for her. I’d be fine with buying a small, reasonable gift for a co-worker’s birthday, but this is different. What should I do?

—Gift Grief

This is such a terrible position to put your employees in. Employers, owners, senior partners, anyone with direct reports who might be reading this column—please don’t ask the people who work for you to buy you a gift—let alone your family members! Alison Green over at Ask a Manager gets a version of this question all the time and has even written a helpful guide for the etiquette of office gift-giving. Since you’re brand-new at this organization and everyone else seems to have resigned themselves to participating, it may be additionally challenging for you to decline this dubious honor, but this is a completely outrageous request, and you should feel no compunction about declining to participate. Hopefully no one will repeat the request of you, especially since you’ve yet to be paid, but if they do, simply say, “My budget won’t allow for that.” Alison also suggests a “no, thanks” or “I’m not able to contribute.” Whatever version you use, resist the urge to apologize.

Dear Prudence: A stranger says my husband forced her to have sex with him long ago. What do I do?

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Dear Prudence,

I’ve done a terrible thing, and I have no idea how to emerge on the other side of it. My fiancée of six years and I are engaged to be married in four months. Here’s the “thing”: I proposed to her in response to an ultimatum and to maybe prod myself into feeling more enthusiastic about the relationship. We have had a tumultuous relationship that has been exacerbated by addiction issues on both sides. She has consistent anger and anxiety, and I tend to pull away and withhold physically.

Despite this, we care very much for one another. She was diagnosed with a neurological disorder earlier this year and has quit her job to find something less physically taxing, so I feel both an emotional and financial burden of care. I’ve seen and ignored so many red flags over the years—how do I know when or if I should act for my future? We are youngish child-free professionals. Is it possible I just haven’t bought in 100 percent and need to dive in with more enthusiasm? I’m feeling stuck and time is ticking.

—Impending Wedding Blues

Diving does not spontaneously produce enthusiasm where none exists. Diving just means you’re going to fall. Here’s what you’ve written on the plus side of your relationship: You care “very much” for one another.

Here’s what you’ve written on the con side: You’ve done a “terrible thing” in getting engaged, your relationship is tumultuous, she gets angry and you withhold, you feel an emotional and financial burden, you’ve seen and ignored a number of red flags, you’re feeling stuck, and the idea of getting married in four months puts you in mind of a bomb counting down. You’ve been engaged to this woman for six years; you say you don’t know when or if you should act for your future, but it’s precisely that attitude that’s gotten you where you are now. You feel trapped in a relationship with someone you care for but don’t actually want to be married to. I don’t think going through with the wedding is going to magically transform those feelings into mutual connection and excitement. I think the time to act is before you get married.

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Dear Prudence,

When I met “Ryan,” I knew he had a girlfriend because I met them both at the same time. From the moment I met Ryan, I could tell he was attracted to me, and though I was attracted to him, I put up a lot of barriers to make sure we never got closer than friends. He and I ended up developing a close friendship. We did art together, played music, and talked about just everything under the sun. I always invited his girlfriend to come along, but sometimes it was just the two of us. In an effort to create more barriers, I told Ryan a lot about my past heartbreak over men who were in relationships but actively pursued me without ever leaving their partners, and how I wasn’t interested in repeating the same mistakes again.

To make a long story short, after a few months, Ryan ended up telling me he loved me and that he wanted to leave “Ashley.” I told him I loved him too, but that I wanted a type of love he couldn’t give me because he was in a relationship and I wanted to tumble, with no restrictions, madly in love. Ryan said that he wanted the same thing as me and told me that I was the woman he wanted to be with for the rest of his life. I trusted that, considering everything I had told him about my past, that he had listened to me when I told him exactly what I wanted.

We started sending love letters to each other. We spent time together reading books out loud and going for aimless walks. We started being physically intimate. Ryan told me he didn’t want Ashley to know that he and I were in love because he wanted their breakup to just be about the problems that they had together and not to drag me into it. Ryan then got “confused” about what to do and repeatedly asked me to hold on to what we had, even though he hadn’t broken up with Ashley. This went on for six months. He continued to send me love letters. Ryan then decided, to my surprise, to stay with Ashley and cut things off with me. And he hasn’t told Ashley about any of this and says he plans to “wait until things get better” between them. I’ve cut Ryan completely out of my life because he knowingly brought me into a situation I explicitly told him I didn’t want. He has lied to me, his girlfriend, and himself.

None of our friends know about what happened, and I feel like Ashley should know so that she’s not stuck in a relationship with a man who intentionally lied to her for almost a year (and continues to). Should I tell someone so they can tell her? I know hearing it from me would not be the best idea. I have no intentions of pursuing anything with Ryan in the future, so this is not an attempt to get her to break up with him so I can swoop in. I’m just wondering if this is a situation where I can perhaps share some information so Ashley can make her own decisions about what to do.

—Failing Boundaries

I think the absolute best thing you can do, for yourself and for others, is to stay out of Ryan and Ashley’s lives. What you’re considering is just another way to continue to tie yourself to their relationship. If there was any part of you that was truly concerned for Ashley’s well-being, you would have found your conscience prodding you to tell her sometime in the last year—not only after it became clear Ryan was never going to leave her. It would be better for you to spend this time and energy in therapy trying to figure out what you’re getting out of this emotionally traumatizing habit and developing strategies for avoiding similar situations in the future.

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Dear Prudence,

A very good friend recently came for an impromptu visit on short notice. I was excited to welcome him and his spouse, but they showed up with their two dogs. We have three dogs of our own, two of whom don’t get along well with other dogs. My guest allowed his dogs the run of our house, even after I mentioned that we don’t allow dogs in most rooms of our home because I’m allergic and like to have rooms where I can breathe freely. Worst of all, his dogs weren’t housebroken. I just sort of gritted my teeth and said nothing after it was clear that my guests had no intention of keeping their dogs in the appropriate parts of the house or making sure they went outside, but inside I was seething.

What can I do to ensure this doesn’t happen again? This isn’t the first time people have showed up at our house with surprise pets, and I feel like the attitude is “you have pets, so anything pet-related must be OK with you.” But pets are like children: I love well-socialized, well-behaved pets whose owners understand basic courtesy, but I’m not a fan of animals running wild around my house, harassing my pets, and eating out of the cat box.

—Not a Pet Hotel

You can say no next time! Your problem was gritting your teeth and saying nothing, and the solution to that is, in the future, to let guests know that you can’t accommodate other pets because your own dogs can’t interact with them safely. Even if another dear friend turns up on your doorstep with surprise dogs and a blasé attitude, that doesn’t mean you can’t say no. In fact, you have to say no! There is no other way to make sure people know that you can’t allow other dogs in your home; it is your only way forward.

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