I Invited the Woman I Was Dating to My Apartment. She Took One Look and Broke Up With Me.

This is part of Breakup Week. We just can’t do this anymore.

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

I’m feeling really blindsided by a recent breakup, of sorts. I (male, 25) met a woman, Betty, on a dating app about two months ago, and we went on several dates over the course of a month. Through our conversations, we have talked a lot about authenticity and honesty in relationships, and she said that she doesn’t play games. We went on four or five dates before she invited me to her place, where she cooked a fantastic meal, and I spent the night. I offered to host our next date and suggested pizza and board games, and she enthusiastically agreed.

On the day of that date, she texted to confirm the time and said she was really looking forward to it. I was, too, and was going to ask her to be my girlfriend. When she arrived, she seemed off and uncomfortable. I was hoping it was just nerves and was trying to make conversation. After only about 10 minutes, she abruptly got up and said this wasn’t going to work out and that she would be leaving now and wished me the best. I asked her what was wrong, and she said, “Well, honestly, it doesn’t seem like you’re ready for guests,” and gestured around my apartment. Admittedly, I don’t prioritize chores, but I did make an effort. I cleared off the kitchen table and made sure there was space for us to play games and have a couple of plates out. I thought she wanted to get to know me, so I wasn’t worried about the rest. I was honestly shocked, given that she had been saying she wanted to know the “real me.”

I texted her a few days later and told her how confused I was about that night. She texted back that she was thankful for that date because I was honest and authentic with her, but that authenticity does not replace basic manners.

—What Do Women Actually Want?

Certainly, some women actually want to play games and get to know you in a dirty living room with just enough space cleared for a couple of plates. But Betty is not one of them. The question you pose in your sign-off makes me want to remind you that not all women are the same, and there are no rules about what they’re allowed to see as a deal-breaker. The person who wants to eat pizza amid your clutter and will see it as a beautiful exercise in authenticity is out there. You’re much better off getting back on the apps and looking for her than trying to convince someone not to be disgusted by the way you live. —Jenée Desmond-Harris

From: “Help! A Woman Broke Up With Me the Moment She Saw My Apartment.” (Aug, 13, 2022)

I had a wedding planned for the end of July that my fiancé and I decided to cancel. We live near his family and decided we would all quarantine for two weeks and then have a small family celebration when everyone’s in town next month. I’ve always dreamed of a big wedding, so I’ve been going back and forth. That was until my fiancé’s brother, Tom, got here. I’d only met him once over Christmas, but he couldn’t stay for long because he went to spend part of the holiday with his girlfriend (whom he has since broken up with). He lives on the other side of the country, so he hasn’t been back much. When I first met him, he had a lot of qualities that I thought I didn’t like. I finally got to spend some quality time with Tom and realize he is actually an amazing guy. I feel really confused. My fiancé is everything I’ve dreamed of since I was a teenager. I think Tom might be the person I never knew I wanted. I’m really torn about what I should do. I thought I wouldn’t see Tom much after he left in a few weeks, but he told me he’s thinking about moving back. I don’t think it would be hard to get my fiancé to put the wedding on hold until we can have something big, but am I being ridiculous in thinking this will somehow buy me time to figure out what I want? Am I delusional in thinking that leaving my fiancé for Tom would ever work out with the family dynamics? How can I figure this out?

—Wondering About My Wedding

Dear Wondering About My Wedding,

Part of this depends on what you mean by “working out.” If your goal is to figure out your own commitments and desires, I think there’s an excellent chance of things working out. If your goal is to leave your fiancé for Tom (who doesn’t seem to have given any indication that he feels the same way about you) and ask your in-laws to throw you a second shower, I think it’s extremely unlikely. If you were to break up with your fiancé because you’d fallen for his brother, you two would probably never become friends, and the rest of your in-laws might take a very long time to come around, if they ever do (unless you are writing to me from within the movie While You Were Sleeping.) But it’s not ridiculous to take your sudden reevaluation of your feelings for your fiancé seriously. What are some of Tom’s amazing qualities (and what made you mischaracterize them as “unlikable” when you first met)? Has he made you realize something’s missing in your relationship? What’s he got going for him besides “amazing”? You say you’ve “always dreamed” of a big wedding and you’ve “dreamed” of someone like your fiancé since you were a teenager, which speaks more to the persistence of your desires than to specificity. What’s Tom got that you never knew you wanted? Do you think your fiancé is capable of developing any of those qualities, and if so, is there any part of you that wants to stick around and find out.

Most importantly: If you made a pass at Tom and he turned you down (which I think is the likeliest outcome), would you still feel that leaving your fiancé was the right thing to do, since you no longer feel the way about him you did when he proposed? There’s no casual, easy way to postpone or call off a wedding; your fiancé and would-be in-laws aren’t going to shrug and say, “No worries, take your time.” You’ll have to carefully reflect and assess whether you think this is a case of sudden nerves that will pass with time or a sign that you really don’t want to do this. But you need to make your next move without getting a response from Tom first. The answer to the question of “Am I ready to marry my fiancé?” can’t rest upon “I want to find out if his brother likes me first.” —Danny M. Lavery

From: “Help! I Want to Break Off My Engagement—to Date My Fiancé’s Brother.” (Aug. 3, 2020)

My first wife “Trish” and I divorced about five years ago. She didn’t want to have sex after the birth of our kids, so I found sex elsewhere. I was very discreet, but she found out after several years; then she informed me “what’s good for the gander is good for the goose” and she started seeing other people too. That was fine with me, as it gave me more freedom and less paranoia about getting caught cheating. Trish asked for a divorce within the year, and since my girlfriend of two years, “Annie,” had been pressuring me to leave Trish, I thought it was the best outcome for everyone. Annie and I got married soon after the divorce was final.

I see Trish every week when we hand off the kids, who are now teenagers, and I dread it. Not because she’s mean or rude … she is warm and generous and funny. I recognize that she hasn’t really changed; these traits were always there, but they were buried under my resentment over the sex thing, the nagging, the financial stress, etc. On top of that, her career took off almost as soon as we separated, but not soon enough for me to ask for alimony. She’s earning more by herself (thanks GlassDoor) than our combined household income when we were together. Her live-in boyfriend (she has told the kids she’ll never marry again, which feels like an attack on me, her one and only experience with marriage) is a well-known writer and together they travel to exotic places, eat at fancy restaurants, and have a crowd of well-known writer friends. They’re even taking the kids to London this summer while he teaches a workshop there.

I am struggling financially and having some health issues—the recent loss of a visible tooth I can’t afford to replace hit even harder than the diabetes diagnosis—and my now-wife Annie has health issues of her own that make her tired and irritable, and affect her ability to work. I used to be mostly content with my life, even when married to Trish, as long as she wasn’t nagging me. Her new life makes me feel terrible. Like the spotty overweight kid at a high school dance. I feel like in the game of divorce, I lost big, and it’s eating me up. I’m resentful that we had money problems when we were together because she didn’t work very hard—she said she was focused on the kids and the home. I hate that my daughter showed me a picture of her mom beaming happiness with her boyfriend on a mountaintop in Patagonia.

I hate the idea of therapy, and can’t afford it anyway, and the antidepressants my GP prescribed don’t seem to be doing anything. Can you help me re-frame this so I can get over it? How do I live in the life I have now, maybe even improve it, instead of going around and around about all the ways it could have gone differently for me?

—Me: 0, Ex: 100

This reads like the fantasy of anyone who’s been in Trish’s position: Leave a cheating spouse and immediately begin thriving in every way, while your ex looks on, full of regret and delayed appreciation for you, with a missing tooth.

But if this letter is not in fact the work of a scorned wife using creative writing to envision a just outcome for her relationship, and is actually your request for advice, I have a few thoughts on how you might begin to feel better:

1. You should grapple with how your relationship with Trish began to go downhill. I don’t perceive even a hint of regret for the infidelity that started all this. It seems to me that before you get to making peace with the mistake you made by looking outside your marriage for sex, you should actually acknowledge to yourself that it was a mistake. You probably felt like you didn’t have any other options and I get that, but there were steps you could have taken before betraying your wife’s trust.

2.

Once you’ve had a chance to sit with that, you can forgive yourself and also remind yourself that you weren’t actually that happy with Trish. You didn’t have any intimacy, you felt nagged, and the most positive word you used to describe your relationship was “content.” So you actually never had the option of being with the current, jet-setting, high-earning, happy version of her. That wasn’t on the table for you. My guess is that a lack of connection between the two of you made your marriage a place where she was unlikely to thrive the way she is now. It’s possible things started falling into place for her after you split because she had the partner she needed, and all of his unconditional support. Maybe, for example, when she was asking him to pick up some household duties while she was in the midst of an intense job search, he didn’t accuse her of nagging but instead happily agreed and also offered to do mock interviews with her. I’m not saying that to shame you, but to suggest that the right spouse can bring out the best in us—and that kind of dynamic is available to you, too!

3. Even as you try to let go of the idea that it could have been you married to Trish 2.0, give yourself permission to feel jealous. Money doesn’t buy happiness, but it definitely eliminates some of the things that can make happiness tough, and you’re not wrong to wish you had the financial security Trish has, especially as you struggle with things like affording healthcare. But then maybe try to replace the jealousy with a different way of looking at your ex’s seemingly charmed new life: What if it’s not an indication of your failure, but proof that a major change in fortune is available to all of us, including you? If Trish went from financially struggling, not working (and I assume being pretty devastated that her husband was cheating on her) to beaming at the top of a mountaintop on an expensive vacation, isn’t that proof that this kind of change is possible? Could you start to imagine it for yourself and maybe look at her as inspiration rather than competition?

4. Keep trying new antidepressants. All the reframing in the world won’t make you feel better if your brain is insisting that your life sucks, so medication might be the most efficient remedy. Also, commit to finding a therapist with a sliding scale and meeting with them for six months. You don’t have to love it! Just try it. Worst case scenario, it will be a place to share all the thoughts you’ve shared in this letter repeatedly, week after week, until they don’t feel as overwhelming.

5. Don’t make the same mistakes with Annie—being critical of her limitations instead of working on your own—that you did with Trish. Two thriving ex-wives would be too much to handle! But on a more serious note, you have someone who loves you, which is more than a lot of people can say. Even if you aren’t thrilled with your life at the moment, you can make it a point to make hers better through simple things like being understanding when she’s tired, trying to cheer her up when she’s irritable, listening to her and affirming how tough it is to live with health conditions, and assuring her that things will get better. In other words, invest in this relationship in the way you didn’t in your first marriage. In the short term, it will take your mind off other people, and in the long term, it could lead to a partnership and life that excites you.—Jenée Desmond-Harris

From: “Help! I Willfully Blew Up My Marriage. Now I’m Seething That My Ex-Wife Is Living Her Best Life.” (May 30, 2024)

I have been dating a man now for eight years who is a loving, awesome person in many ways. He adores me, and he treats me like a queen. The problem is that I don’t want any of it anymore. He struggles with alcoholism and anxiety, cannot hold down a job, and still lives like a college student just scraping by, despite being in his 40s. I decided four years ago that he’s not what I’m looking for, as a divorced mother of two, despite his many good qualities. But because of all these issues, mainly that he has no money, he still has not left my space.

He lives in denial and treats our relationship like we are mutually involved when he knows exactly how I feel. I want him to move out, and it always comes down to the fact that he has no money and really can’t get another place in our ridiculously expensive town. I don’t have the heart to throw him out on the streets, and he does not have a single friend who would let him move in due to his history with drinking. He goes to a therapist, and he says he understands and doesn’t want to hold me hostage in this relationship, but it just does not stop. I don’t want to live with resentment and anger toward a dependent person who obviously cares more about his own self-preservation than releasing me from the relationship I no longer wish to be a part of. I have said and done everything short of changing my locks and physically restraining him from my home (which I just cannot do). What can I do to finally initiate change?

You have things backward, I fear. You say you can’t kick him out because then he’d be completely helpless, when I think he’s completely helpless because he knows you will never kick him out. You do not need him to “release” you from this relationship, because breakups do not require a unanimous vote. Presumably he managed to keep body and soul together before you two started dating, so I don’t think it’s unreasonable to believe that he’d find a way to continue living if you two ever really broke up. If you really want to move on, you’ll have to let him solve his own problems again (or fail to solve his own problems, or find another girlfriend to solve them for him, as the case may be). But that will require letting go of the fantasy that he’s absolutely dependent upon you, that you’re the only thing standing in between him and the streets. He’s proved fairly ingenious at finessing his way into a rent-free living arrangement with his ex-girlfriend for the last four years! You must give him at least a little credit for resourcefulness. I wonder, if he’d applied some of that resourcefulness elsewhere, if he might have found one or even two possible alternatives, even in your very expensive city (or a less expensive city).

You can even offer to front him first and last month’s rent, if you just want to throw money at the problem. I do worry that once you start giving him rent money, you’ll never stop, but you’re already paying his rent now, and at least in that scenario you get to have your bedroom back to yourself. Another option is to consult local tenant laws, then evict him. If you can’t bring yourself to change the locks, hire a locksmith to do it for you, a moving company to put his stuff neatly into storage, and a claim ticket so he can pick it up at his earliest convenience. If that sounds as daunting as trying to walk to the moon, consider attending a few Al-Anon meetings to see if you can find solidarity and support there. But there’s nothing cruel or unusual about telling your ex-boyfriend he can’t live with you forever. Your distress and concern are readily apparent, and I am sorry you’ve been suffering over this decision for so long, but you already know that nothing about this situation is going to change until you decide to do something different. If you simply can’t bring yourself to kick your ex out, then prepare yourself to live with him for the rest of your life. He seems perfectly content to be your roommate and your dependent, forever. —Danny M. Lavery

From: “I Dumped My Ex-Boyfriend Four Years Ago. He’s Still Living With Me.” (Oct. 31, 2020)

My sister has never had a romantic relationship that ended well. Most recently I objected to her dating my fiancée’s brother, but she told me it was none of my business. A month before my wedding, they broke up spectacularly. I really don’t care who cheated or who got drunk with whom—I am tired of it spilling over into my life. My brother-in-law has been very quiet and personally apologized to me. My sister got drunk at my bridal shower and picked a fight with my sisters-in-law. My mother and I laid down the law; my sister sulked. She burst into tears and said that we didn’t care about her broken heart. I am ready to tear my hair out. My mom tells me to give my sister “time.” But she only dated him for three months. I have been planning my wedding for three years! We are paying for everything ourselves. My sister and brother-in-law are both in the wedding party. Can I just ban my sister for my peace of mind?

My instinct is that your brother-in-law got drunk and cheated on your sister, because you sound angry enough with your sister that if she’d done that, you’d have mentioned it as further ammunition in the case against her. That doesn’t mean your frustration with her isn’t justified, just that I wouldn’t give him too much credit for being “quiet” and privately apologizing. If you ban your sister from the wedding party, do you think she’ll still want to attend the wedding? Do you trust that if she did, she’d be able to keep herself from getting drunk and starting a fight? Would you and your fiancée consider asking your brother-in-law (who, let’s not forget, is just as responsible for the “spectacular” end of their relationship) to step back from wedding-party duties? If not, do you think you can talk to your sister about how to best prepare for your wedding day without dredging up every breakup she’s ever had and making it clear that you think she’s the common denominator in all of those bad relationships?

Whichever route you choose, it’s important to stay focused on what your sister thinks is possible for her on the big day: If she can’t be polite but distant to the groomsman who just broke her heart and you’re not willing to ask him to step back, see what she needs in order to keep from relitigating their breakup in public again. Maybe that’ll be permission to leave early or a promise not to drink or talk to his side of the family. Maybe it’ll be something else. If even with the passage of time your sister seems inclined to prioritize her admittedly short-term heartache over a peaceful wedding day, you may have to lay down the law and ask her to either commit to keeping it together or skipping the ceremony entirely. —Danny M. Lavery

From: “My Sister’s Spectacular Breakup Is Destroying My Wedding.” (May 23, 2019)