“He Proposed While I Was Trying to Break Up With Him!”

The other day I tried to break up with my boyfriend of one year. However, during the breakup, he pulled out the engagement ring he bought and proposed. I ended up walking back on the break-up because I felt so guilty.

But now, as a few days have passed, I am really mad. We had talked about marriage before, and I asked him not to buy an engagement ring. One big reason was I was having doubts about our relationship and another reason was he couldn’t afford the ring.

Now I feel stuck. He went into debt for a ring I wasn’t ready for and now really don’t want, and I can’t stop feeling guilty. Do I give him another chance or do I really break up with him? What do we do with the ring? — Yes By Guilt

He proposed while you were trying to break up with him?! Well, all bets are off if he proposed as a way to manipulate you to stay with him. That’s so not fair. And it’s not fair if he’s continuing to guilt you to go through with this engagement because he bought a ring he couldn’t afford and has a bunch of debt now. That’s not your problem! You didn’t ask him to buy a ring. You didn’t even want it! You were trying to get out of the relationship, and now, when you should be a couple pints into some breakup Haagen-Dazs before moving on to whatever the next better thing is on the horizon, you feel stuck in an engagement to a man you don’t want anymore who now has a bunch of debt over a ring you didn’t ask for.

MOA! How? Tell him: “Hey, John, when you proposed the other day while I was trying to break up with you, I was so stunned — because, you know, I was breaking up with you, and, also, there was this ring you had always said you couldn’t afford and I didn’t know what to make of that — so I didn’t have my wits about me and, now that I’ve had a few days to consider everything, I know it’s the right thing to give you this ring back and tell you I can’t marry you. I’m sorry, but all the reasons that led to me wanting to break up with you in the first place still stand and. While I appreciate the gesture of a proposal and a ring, getting married isn’t the right choice for us.”

As for what HE does with the ring (he, not you, because you will have given it back), that’s not your problem. Hopefully, he has a good return policy on it. But if not, he’ll have to find a place to sell it and try to make as much back on it as he spent so he can dig himself out of the debt he incurred trying to keep you in his lair. So, give the ring back and go pick up some ice cream, fire up some Netflix and get on with the rest of your life. Without this guy and his ring and all his weirdness.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Sunshine Brite says:

    Why would you give that another chance? Finish the break-up!

    1. Avatar photo Mr. Cellophane says:

      Finish Him!!
      And don’t forget to “double Tap”.
      Sorry, video game, flashbacks!

      1. Sunshine Brite says:

        Bahahaha love it.

      2. Ah good ole Mortal Kombat! hahaha

      3. My favorite part of MK was having to break the wood all the way up to the cement. My brother & I played this game ALL.

      4. ALL. THE. TIME.*

      5. No, I liked ALL. Like, that’s the only thing we ever did in the history of ever and we knew all of the secrets and were MK masters. Stick with just ALL. 🙂

  2. Don’t let yourself be manipulated by this ring, LW! Don’t feel guilty, you didn’t pressure him for a ring or make the decision for him to buy it. Like Wendy said, this is 100% HIS problem, not yours.

    1. Also, I’m kind of getting more angry at him the more I think about this. Either he’s tone-deaf or manipulative, and both are terrible, terrible traits. Also, has he treated you more like an object of his or a stereotype of a female in the past? I’ve had some friends in situations like that. If so, this is way more about him than you and you’re not actually hurting his feelings, you’re hurting his ego.

      1. Sunshine Brite says:

        It worries me not that she said yes in the moment getting caught off-guard, but that she’s considering going through with it just because he asked. That to me says that there’s something weird with their dynamic already or that she gives into expectations/is a people pleaser which can get overwhelming (says a people pleaser)

      2. Agreed. I’m sure he tried it because he had a sense it would work, for whatever reason.

      3. I’m a total people pleaser and our dynamic is totally unhealthy. I want out of the relationship because as a people pleaser, I can’t be with a person like this.

      4. He definitely does the female stereotype thing.

        And yeah, the more I think about it, the angrier I get.

      5. Then you need to get out asap, but I think you already know that.

    2. Avatar photo Raccoon eyes says:

      Ummm, YES. Your ex, errr, fiance I mean, is a manipulative d*ckface. You said “dont buy a ring,” but he did and then proposed WHILE you were trying to break up with him? RUN AWAY, this does not otherwise end well

  3. Just…wow. That’s manipulation for you! First he tried to get you to stay by proposing while YOU were breaking up, THEN he guilts you by saying he is in debt because of the ring. Wendy is definitely right that isn’t your problem. No wonder you want to break it off…he sounds like a manipulative jerk.

  4. How not to be manipulated: break up with him, but say you are keeping the ring. Within two days, he’ll be so angry that he won’t be guilting you into staying anymore. Then you can petulantly throw the ring in his face, and … you’re done!

  5. Avatar photo Mr. Cellophane says:

    If he used any kind of reputable jeweler at all, he should be able to return the ring NQA. In my experience, having been told “no” once, jewelers are pretty understanding if she says no.

    But of course, this is not your problem!

  6. Avatar photo suzyinthesky says:

    “trying to keep you in his lair” !!! ha ha, priceless, Wendy! seriously, LW, WWS.
    Give the ring back, then buy ice cream, then yoga pants and Netflix. Enjoy!

  7. Unwanted_Truth says:

    Whoa whoa whoa there ladies!! Back up and tick here. Either I do not know how to read, or every single last one of you, Wendy Included, missed two big things here.

    1. She said she had TRIED to be break up with her boyfriend, Tried. That is extremely vague, HOW was she trying? Did she even get to the part of saying it’s over before he presented her with the ring? How much into trying was she at this point, did he even realize this? Jesus christ talk about jumping on the guys back way too fast.

    2. She didn’t even state in the letter what her answer was to him. Did she say yes ok i’ll marry you? Did she say let me think about it?

    3. We don’t start a sentence with AND.

    I will say though, regardless of those two things, dude should have known better than to buy the goddamn ring in the first place since she had already told him NOT to. I also wonder, was it only in your head/heart that you were doubting the relationship? Or did you tell me him this while telling him not to buy you a ring?

  8. It’s been a LONG time since I commented (usually I’m Tudor Princess), but I had to say something about that there ring he bought:

    I worked at Jared’s for over a year. If he purchased it at a reputable company like Jared’s, they have what’s called a Broken Engagement return policy. Basically, if the engagement is broken off within a certain time frame he can get most of his money back. I say “most” because there might be a few fees he can’t get back. He needs to check with the place he bought the ring. Anywhere else, dude is SOL.

    So…give him this info as you’re breaking if off. Best of luck to you!

    1. Thank you for this. He got from a very reputable jeweler who happens to be a family friend. I’ve heard from a few others that there is a good chance they will take it back, minus the fees. Helps squash that voice about the money.

  9. I think the OP said yes cause of the excitements of being engaged and having a ring, not because she felt bad for him. Any who, its an easy fix , Just take it back and break up with him.
    If she really wanted to be done with him she would have done that already.

    1. Avatar photo Stonegypsy says:

      I don’t think that’s the case at all. Being guilt-tripped is a thing, and the sudden shock of “I spent a bunch of money and went into debt on this thing with the assumption that we’re staying together” would be enough to throw anyone off their breakup game

  10. Break up with him.

    Give him back the ring and he can figure it out from there.

    His terrible financial judgment and refusal to listen to your request not to buy an engagement ring is yet another reason to break up with him.

    Best wishes!

  11. I’m curious as to how things happened. Like did he realize you were breaking up with him? Or were you just building up to that in conversation. I’m just so curious how a conversation goes from I think we should see other people to no let’s get married in someone’s head. Unless he either didn’t want to hear it or really just does not get it. Like Wendy said just tell him you changed your mind and then let him deal with the ring. You didn’t force or ask him to buy it, at this point it’s on him to deal with getting his money back.

    1. hobbesnblue says:

      Yeah, I’m tempted to give him some modicum of the benefit of the doubt, since it’s not clear to me from the letter whether she was already breaking up with him or just starting a serious “we need to talk” conversation that she intended to lead there. That doesn’t save him from the “tone-deaf” criticism, but perhaps from part of the “manipulative” one.

    2. I said “I think we should break up.” The engagement ring came out because he wanted to show me how committed he was to the relationship.

      He has a knack for ignoring the bad and just seeing what he wants in a conversation/situation.

      1. Yikes! Yeah give the ring back be strong. Maybe meet in a public place, if you live together have a plan for being out already before the talk, and maybe even have a friend waiting for you somewhere nearby that you can meet up with after.

      2. LW, I think having a friend ready to meet you at X time (and possibly waiting nearby) is a good idea. You might find it easier to actually go through with it this time, as you have a reminder not to be emotionally blackmailed again. Plus, the friend would be looking out for you, while he obviously has his own motives.

  12. Oh my. Was it obvious you were trying to break up with him? In any case, you shouldn’t be dating, engaged, or married to someone out of guilt and he shouldn’t want you to stay with him out of guilt. Break up with him and give the ring back. One of my college buddies got dumped after he’d bought his then-girlfriend a ring but before he’d found the ideal time to propose — they can be returned.

  13. It’s reasons like this that I think you should know your answer will be yes before you propose. I just am imagining how this went down:
    Her – “Honey, we need to talk”
    Him – “I agreed”
    Her – “Things aren’t working, we need to change”
    Him – “I still agree”
    Her – “I’m breaking up with you”
    Him – “By breaking up with me, you mean marrying me, right?” *gets down on one knee”
    Her – “Yes, that’s exactly what I meant”
    He just sounds tone deaf and manipulative.

  14. This happened to me!!! Not exactly, but less than a month after my college boyfriend and I had a huge, sobbing, fight in a car in the Best Buy parking lot on Black Friday (we were visiting my parents for Thanksgiving, and couldn’t fight at their house) which ended with me saying something to the effect of “we cannot talk about getting married until we fix all of these issues we’re having, so please don’t even think about proposing,” he proposed to me- in front of his entire extended family on Christmas Eve a 4-hour drive from home- because he knew I would have no choice but to accept (or risk humiliating both of us in front of his whole family, and leave myself stranded far from home).

    In my case, my ex was absolutely manipulative and emotionally abusive, and this was just one example. I don’t want to project, but you could be in a very similar situation. Regardless, the best case scenario is that he’s oblivious and tone deaf, and the worst is that he’s a manipulative asshole. Either way, you’re now engaged to a man you don’t even want to be dating. End it, give the ring back, and consider this a bullet dodged.

    1. Sunshine Brite says:

      I’m glad he’s your ex! Sounds similar to a lot of siutations where a public proposal is used which is another reason why I dislike them (besides them being the exact opposite of what I wanted personally). The fact that you would be stranded is horrible.

    2. Avatar photo Stonegypsy says:

      Why would anyone want to marry someone that they had to manipulate into accepting their proposal? I don’t get it. Like “I know you don’t want to marry me so instead of entering into this huge life altering commitment with someone who’s happy with me, I’m going to make it impossible for you to say no!”

      1. Avatar photo Moneypenny says:

        Right! Exactly what I was thinking. What a horrible foundation for a marriage.

      2. I honestly think it was a combination of fear of being alone, and pressure from his family. The whole situation was just screwed up. Luckily, this was almost 10 years ago and I’m now happily married to a guy I actually wanted to marry 🙂

      3. The funny part is that my husband did propose in public (although most of the people around us weren’t aware) and even farther from home. But we’d already been talking about getting married and were just waiting for an occasion to make it official, so that was totally fine.

      4. “a combination of fear of being alone, and pressure from his family”

        This is his motivation exactly

      5. All I can say is that the more parallels you see between my situation and yours, the more you need to end this, like, yesterday. Seriously, it will be hard for the first day or two and after that you’ll feel nothing but relief!

  15. I can’t believe he even imagined that would be a good idea! Like everyone else said, you need to still break up with him.

  16. SMH some people really just can’t take the hint. I don’t know how anyone couldn’t pick up on the break up tone, and then still pull the ring out.

  17. Avatar photo Addie Pray says:

    First, I agree with what Wendy and everyone else said.
    Second, I’m kind of dying to know why exactly you were breaking up with him in the first place. Honestly it doesn’t matter. It’ likely is as Wendy predicted – his tone-deaf, manipulative ways – but… but I was just curious.

  18. I actually knew a girl that this happened to! She was trying to break up with her boyfriend (to be with the guy she had been cheating with, their relationship was kind of a mess). But during the breakup talk, he pulled out a ring and proposed. She immediately accepted and they actually went through with the wedding. I’m not sure how they are today. She was a close friend to one of my close friends but I haven’t received any updates on their drama lately.

  19. bittergaymark says:

    Everybody is ripping this guy a new asshole, but the LW is maddeningly vague here. How far into the breaking up speech. Had you ACTUALLY said: “It’s over, we’re breaking up!”? Or were you instead dragging your feet — in the midst og hemming and hawing with wonderfully vague phrases such as: “Where is this relationship going… I just don’t know if you really care about me…” And THEN he whipped out the ring. Because those are two VERY different scenarios…

    1. I said “I think we should break up.” It’s tough because my reasoning is frankly, vague. For me the relationship doesn’t feel right and I no longer want to be with him and I couldn’t give him the concrete reasons why the break up was happening.

      I’ll take total blame for walking back and not being stronger in my break up language. But there he was sobbing, showing me the ring, and telling me he would have nothing if he didn’t have me.

      1. JESUS. Talk about a flair for the dramatic. Yeah, WW and EES.

    2. Avatar photo Raccoon eyes says:

      Huh, good call, BGM. I think I just read it and had the immediate, “Oh, hell NAW!” knee-jerk reaction, but you are right, the language isnt clear that she had crossed the Rubicon, if you will, of the actual breakup. “I ended up walking back on the break-up” strikes me as unusual language too, on second glance.
      Eh, my thoughts are still the same though- NACHO PROBLEMO. Break it off. Seriously, isnt “he went into debt for my ring” like, THE WORST reason ever to get married?

  20. Letter writer here. I started out our break up conversation with “I think we should break up.” He kept pushing me to why I wanted to break up and all I could say was “It just doesn’t feel right to me,” which is true. I don’t have reason A,B,C why I wanted to break up with him but my gut tells me it’s over.

    He started crying and then ran to his bedroom and came back out with the ring. While sobbing, he showed me the ring and told me he was nothing without me.

    Total clusterf**k.

    1. Last piece of clarification- After seeing the ring, I said “ok, well, let’s talk about our relationship. I’m not saying yes to the ring, but I’ll give us some time to figure things out.”

      I have the ring, but I’m not wearing it.

    2. You don’t need to have A,B,C objective external reasons to break up, all you need is the reason that you want to break up. That is enough. And you have more than that, you have the reason that it doesn’t feel right to you. So, actually, you had reasons A and B already, plus now you have reason C (emotional blackmail over the ring).

    3. Avatar photo something random says:

      Oh my. Well there simply isn’t an easy way to break someone’s heart. My vote is for as clearly and quickly as possible. Wendy’s lines were good.

    4. Bittergaymark says:

      Okay, well.. then yeah. What he did what was obviously a last ditch effort to save things, which while not the coolest move… I kind of get why he did this as, you know, he had bought the ring. Which means to me that his feeling at the time he bought the ring were sincere. Look, if I were him, and I am standing there with a ring in my pocket or a home in a drawer. I might have thought, well, fuck it, I have to at least try. If I don’t, I’ll always regret it.
      I would have stuck to my guns more if I were you. But you were blindsided so I see that side of it, too.
      However, the time has now come to be firm. And to end things. Duh… NEWSFLASH! It doesn’t have to be some big blow out and some big “HOW COULD YOU DO THIS TO ME! — YOU MANIPULATIVE ASSHOLE!!” speech (as some seem to be suggesting) on your end. Instead, just calmly say…. “Upon further reflection, I simply don’t think we are right for one another. I really truly don’t. Do you really want us to get married with all this doubt? I don’t. Think about it…… we can BOTH do better…” And then, simply leave it at that.

      1. Avatar photo Addie Pray says:

        BGM, you are such a romantic!!!!! You know, with the “I have to at least try, If I don’t, I’ll always regret it” stuff. Who knew. 😉

  21. OK- Being upset that someone is breaking up with you is a normal reaction. Maybe even some bargaining (ie, “I promise I’ll do better,” etc). But demanding the break-up initiator provide valid reasons for the breakup is already some worrisome territory. The only good reason someone needs to end a relationship is not wanting to be in it- period. And pulling out a ring at that point is beyond icky. I really think he knew what he was doing- trying to manipulate you into staying in a relationship that you don’t want.
    The relationship didn’t/doesn’t feel right because you feel like you’re being pressured to be there- by him, maybe by others’ expectations, by your own expectations. But staying in a relationship that already doesn’t feel right and shows signs of some manipulative/abusive tendencies is WAY worse than hurting him and failing to live up to those expectations.
    My grandma died shortly after my “I never wanted to be engaged” engagement ended. I’d stuck it out as long as I did because we were living together, and because I hated to let down all of our friends and family and embarrass myself by admitting how bad our relationship had been all along. During my grandma’s wake, one of her friends came up to me, hugged me, and whispered in my ear, “I heard you un-engaged yourself. Your grandma was really happy.”

    1. Definitely agreed – you don’t have to give a long list of reasons as to why you want to break up. If it doesn’t feel right to you, that’s enough. That’s something I’ve learned as I’ve gotten older.

  22. WWS was SO PERFECT!! Please take her advice, and PLEASE send an update… SOON!!!

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