So my girlfriend Rose (24F) and I (23M) have been dating for 4 years and lately she has been putting on the pressure of the ring. We have both love each other and have talked about getting married as it is a sure thing. I have not proposed yet as I just graduated university and dont really have a good job yet, student loans, need to save for a house etc. We currently dont live together. Weve been waiting to move in together once i get a good job as we will likely have to move to a bigger city for said job.

In July we are going to italy with her sister Nora (26F) and her boyfriend Mitch (27M) after I write a big licensing exam which i have been studying for. Mitch and Nora live together and have been dating for about 3 years. Mitch texted me about a month ago telling me he was going to propose to Nora while we are in italy and plans on telling Rose before hand so we can prepare accordingly (he has not told her yet). When he told me this, Rose had not started putting on the engagement pressure yet so I didnt think of proposing in Italy, tbh until recently I probably wasnt going to propose until next year once Rose and I move in together and I have a better job. Rose has now even said things like “why dont you propose in italy, it would be perfect”. My only argument being that we would possibly have a somewhat long engagement (>2 years) becasue of moving and what not which Rose has shut down pretty easily as she said she would rather be engaged than a girlfriend and planning the wedding would be easy as she has eveyhting already picked out lol.

The issue is can I propose to Rose when Mitch is also proposing to Nora on the same trip? Im not sure if the sisters would care. On one hand they are pretty good at sharing things and its possible as long as we propose in seperate outings (ie. nora and mitch go to one restaurant and we go to another or something) they could both come back with a ring on their respective fingers and be excited for themselves and each other. On the other hand they would think its very inconsiderate of Mitch and me (mostly me) for not giving them their own moment.

Theres also the fact that Mitch had the idea to propose in italy first. I am going to ask him what he thinks of all this as well. Ultimately i will back down if he says he wants it to be their moment but if he doesnt care than should I also propose in italy?

28 comments
  1. Don’t do it. Wait till you’re ready. Don’t fall for the pressure. If your plan is to do it next year follow through. One year wait in a fresh relationship like yours shouldn’t be too bad.

  2. I think the only reason Rose is putting pressure on you is because Mitch has told her and has been planning with her. It’s got her oolahs all in a twist.

    If you’re going to do it on this trip, it’d be most clever to dupe both sisters into planning the same proposal event. Shoot, you could even get them each to hold a camera and record it even.

    I’m not gonna lie. If I wasn’t going to propose, and Mitch isn’t going to save the proposal for the last day, this vacation looks to be a disaster in the making. Your GF is going to have so much unmitigated disappointment. Every time she has to see her sisters excitement and ring, she’ll be jealous and resentful.

  3. I dunno man, you’re kind of talking about engagement like it’s something you do when your girlfriend bullies you into it, vs. when you’re both ready and excited. And I do think horning on on Mitch’s plans to propose is shitty even if he agrees to it.

  4. Your girlfriend wants to make this about her. You are reasonable in your timeline so just sit your gf down and say “I want to do it the right way, I want it to be perfect, I don’t want to copy Mitch as if I didn’t love you enough to come up with something worthy of us, when the time comes, I will propose and it will be great but for now, you need to be happy for your sister and allow her to have her moment”.

  5. If you had been planning to propose on this trip when Mitch told you his intentions, that would be one thing. But until you and Rose heard about it, it wasn’t even on your radar. So I think it would be really selfish to propose on this trip and possibly damage some friendships. You have some milestones you want to hit before proposing, I think you should make those clear to Rose and work together on a plan to get there. And selfishly, if Rose gets engaged a little later amd staggers her wedding planning with her sisters, there will be less worry about divided attention from family, competing dates and she can learn the dos and don’ts from her sisters legwork.

  6. I wouldn’t. “They are pretty good at sharing things” doesn’t mean they would *enjoy* sharing a major milestone.

  7. Don’t do it. You’re hijacking an idea from your future SIL. You’re not in the position to even get married. Don’t be that person. Let Mitch have his moment that HE planned. Neither you nor rose had the idea for an Italy proposal on this trip and it’s tacky to take Mitch’s plan for your own.

    Unless you want to burn this bridge say no and tell rose that you will propose in your own way on your own time

  8. 1. This has a strong potential to backfire.

    2. It’s generally wise to wait until after you’ve lived together to propose. Living together is a bigger adjustment than most people expect.

  9. I’d say do not propose, but I think there is a way around that- read to the end for that.

    You weren’t even thinking about it, and Mitch claimed it first. Mitch is going to involve your sister and likely will want her help during the actual engagement. Sure, it is a group trip and no one gets to “claim” what other people do, but it is in super poor taste to hear that someone is going to do something special so then you want to do it too.

    The sisters will likely not be happy to be engaged at the same time, and Mitch is likely to be pissed too.

    Let Mitch have his moment and Rose will be quiet about proposing on the trip once she finds out what Mitch is up to. You can even talk to Mitch about helping you out by telling Rose sooner rather than later and asking him to help you plan a proposal for when you are back. If you really like Mitch, you could even be like “Rose is giving me a bunch of shit about proposing in Italy. I don’t want to steal your thunder so could you let Rose in on the plan now, and then I need your help figuring out how to propose to Rose.”

    If you start there, then MAYBE you could both propose in Italy. That could be a cute story if it is very carefully planned. For example, Mitch proposes on the first night, you and Rose are ready to take photos and with flowers and all that. The next 3 days of the trip are all about their engagement. Give them their romantic holiday and all that. Then on one of the last days, Mitch talks to his now fiancé about how you are planning to propose too- sisters getting engaged on the same trip- and you and he spoke about it before the trip. So now she is on board and her moment, and now can help you propose. This only works if Mitch is fully in, you both know the sisters well enough to know about jealousy issues and all that, and the trip is long enough that there are multiple days between proposals.

  10. You will ruin your relationship with your in-laws if you do it on the same trip.

  11. Dude, let the trip be about her sister and her boyfriend.

    Stick to your reasonable plan to have at least some form of security before proposing to your girlfriend.

  12. Putting aside the tackiness of your gf’s plans, you’ve admitted you’re not ready and you don’t appreciate being rushed into an engagement. These are things you need to communicate otherwise your girlfriend is going to keep getting carried away.

  13. Your vision of the future is not the same as your girlfriend. You talk about **your** timeline. That’s how you refer to it as.

    Her timeline only seems to make it down the aisle.

    What are **her** contributions to saving for a place to live together? For a wedding? Does **she** have solid employment that **she can support herself** on? Is **she** going to keep working during the planning of said wedding and after? What are your plans for kids?

    You only talk about your plan to save for a house and wanting to get a better and more stable job. All you talk about her is wanting a ring and a wedding. To the point she is bulling you into it.

    Do not propose in Italy. The obvious being to not steal it from Mitch and Nora. But seriously dude, your post screams that you are not ready to get engaged or married. In fact, it almost talks like you don’t want to but feel you have no other choice.

    Man, you have so many options. You don’t even live with her yet. Don’t let her bully you into something you, quite frankly, don’t want. At least not in for foreseeable future.

  14. Do not propose on this trip!! This is GF’s sister’s engagement; it would be wrong to spoil it

    Do not propose until you are ready and not being forced into it!!

    Make sure to use condoms, before you get forced into marriage!!

  15. Have you tried telling her that it’s not fair to her sister to try to hijack what you know is going to be one of the best days of her life?

    And that you’ll be able to make the proposal more special by not trying to one up her sister?

  16. Hi OP – plan your own thing, later, on your schedule. Don’t hijack the Italy proposal; DO tell your gf about the other engagement beforehand (if you trust her not to spill the beans) and let her know that because of that, and because you don’t want you/her to have to share your engagement moment, you will not be proposing on the trip and are planning otherwise (but it won’t happen quite yet).

    If she has hope she will get engaged in Italy and it doesn’t happen, she will be sad. She may tell her friends she is hoping for/expecting it beforehand. If you don’t propose AND someone you are travelling with gets proposed to, she will be doubly bummed. So you need to quash her expectations fully!!!!

  17. You should wait and move in together before proposing. It’s one thing to be in love when you don’t live together. It’s something else entirely when you live together. There is lots to learn about how the other lives

  18. Don’t do it. This was Mitch’s idea, and honestly you sound like you don’t even want to be engaged right now, which is perfectly okay. Why is your gfs wants more important than yours?

  19. It would be one thing if you were pumped and ready to get engaged, and had planned to do it during the trip – in which case I’d suggest talking it out with your BIL. But that’s not it.

    Your girlfriend wants the *story* “it was *so* romantic, he proposed in Italy!!”, which is kind of sad – maybe I’m too practical, but I’d think it much better to get engaged when, ya know, my partner and I were truly ready for marriage and not just to have a *cute engagement story*.

    Don’t ask Mitch, for God’s sake, don’t put him on the spot – you don’t wanna get engaged now, own it up with your girlfriend, don’t make this a “Mitch said no” situation, or “well, I guess you (gf) wanted to get engaged, so I proposed even tho I didn’t think it was a good idea”.

    I think… Neither of you are old enough to even be engaged, let alone get married.

  20. This would be really selfish of you. I would be pissed if I was Mitch and Nora. He gave you advance notice of his plan and now you are trying to steal it. It doesn’t even sound like you really want to propose…

  21. There are so many things wrong with this question, OP.

    You open by saying your gf is pressuring you to get engaged, but you don’t feel ready (which is good for you to be able to assess the situation), but then you follow up with two **MAJOR** red flags:

    The first being: you’re ignoring your reluctance and allowing yourself to be pressured into getting engaged.

    The second being: Not only are you allowing yourself to get engaged, you want to hijack your gf’s sister & boyfriend’s moment and propose simultaneously. What’s the logic? Misery loves company? Dumb and dumber?

    Getting engaged before cohabitating is a non-starter if you ask me. While you two have dated, you’ve no idea if you’ll be able to live together. Moreover, you’ve already stated you’re not ready – yet are letting yourself get pressured into it.

    So many red flags. SMH.

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