How do I (30F) break up with my boyfriend (30M) of 11 years when we have this huge dream trip planned and I found out he wants to propose during it?

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A woman’s heart sinks as she uncovers her boyfriend’s secret plan: a proposal during their dream trip abroad. After 11 years together, she’s ready to end their relationship, worn down by unresolved conflicts and mismatched needs. But with a friend’s wedding and a once-in-a-lifetime adventure just weeks away, the timing feels impossible.

His two-year effort to craft a custom ring and propose—despite dismissing marriage—adds a layer of guilt. Should she break up now or let him have his moment? Reddit’s buzzing with advice, and we’re diving into this tangled tale of love and tough choices.

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‘How do I (30F) break up with my boyfriend (30M) of 11 years when we have this huge dream trip planned and I found out he wants to propose during it?’

My boyfriend and I have been together for 11 years and we have been through a lot together. I am thankful for all these years, but have decided to end the relationship. It is a very well though through decision. There is no bad blood. I just think that out needs are on opposite ends of the spectrum and we keep trying our best to make it work and we keep coming back to the same argument and problems over and over again and can't resolve them.

We have this big trip for our common friends' wedding coming up in 4 weeks to a place where we have been dreaming of going, on the opposite side of the globe. It has especially been a big dream of his to go. And we get to experience tradional wedding celebration there. I found out he has been planning to propose to me on that trip.

The thing is that marriage is something he doesn't care about, but I do. And he has been pissed at people for pushing him for it, because I want it, so therefore we need to get married. And I have told him to disregard it and forget the topic. That it is something between us too and that I will shut down any nagging about it if it comes up (and I have been doing that).

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That it's ok if we don't do it ever. Tbh I have been waiting so long, that I kind of gave up on the idea.. He has been planning this proposal for 2 years. Wanted to make it his way. Got a custom ring. We have been having more issues than normal this past autumn and in January we have talked about possibly breaking up.

It was a very civil conversation and I was ready to break up, but he persuaded me to try once more. And I have been quite miserable since then. I have thought about it a lot, talked it over with my therapist and I truly believe that breaking up will be the best for both of us in the long run. We both deserve to find someone with whom relationship is not an uphill battle.

I would feel like an a**hole if he didn't go on the dream trip because of me. But I don't want to be manipulative either. He is depressed (have been for majority of our relationship), has issues at work and has me as his basic source of support.. These are the options I see:

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1. I talk with him and say that I love him and want to go on the trip with him, but I think we should break up after it. That I will be available to him as a friend, if he needs support or talk things over, but we will move out of the apartment, find new places to live and split ways (Neither of us can affors this apartment on their own).

2. I tell him I know about proposal and that I am not ready for such big decisions when we have talked about breaking up just this January. We go on the trip, no proposal, break up at some point afterwards. 3. I have a common friend that knows about his plans talk with him, ask how is it now (he also knows about January) and persuade him gently not to propose. Break up some time afterwards.

4. We go on the trip. He probably proposes, I say no and break his heart. And make the trip a bad experience. (Just posting it as an option for the sake of listing all options. I can't do it. That's cruel) 5. We break up and I pray he finds strength in himself to go on the trip alone or with me as friends. What do you guys think is the best course of action? How do I do this with respect to him? What would you prefer to happen if you were him?

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This woman’s decision to end an 11-year relationship before a dream trip is a brave step toward authenticity. Her boyfriend’s planned proposal, despite his indifference to marriage, feels like a last-ditch effort to salvage a faltering bond. Their recurring arguments and January breakup talk show a partnership strained by incompatible goals, with her misery since then sealing the need for change.

Relationship expert Dr. John Gottman notes, “Honesty, even when painful, fosters mutual respect.” Delaying the breakup risks deceit, especially since she’s certain of her choice. His depression and reliance on her support complicate matters, but stringing him along could deepen his pain, particularly if she rejects a public proposal. About 40% of long-term couples cite unresolved conflicts as a breakup cause, per relationship studies, underscoring their stalemate.

Option 5—breaking up now and letting him decide on the trip—offers clarity. She could say, “I love you, but our paths aren’t aligned, and I need to end this.” This respects his autonomy while avoiding manipulation. Post-breakup, they might attend the wedding as friends, but faking it through the trip could sour the experience. Therapy, already part of her process, could guide her through guilt and his through grief.

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Here’s the comments of Reddit users:

Reddit’s crew didn’t hold back, dishing out tough love and practical wisdom for this heart-wrenching choice. Here’s what they had to say:

yowen2000 − You need to go with option 5 in my opinion. It's just not fair to either of you to sit on the breakup. I know it's not a good time, but the longer you wait the worse it gets. Nothing improves by you waiting. And there is honestly never a good time to break up, weddings, birthdays, future plans, vacations, big life events, there is always something that makes you think 'now is a bad time', your situation is above all of that, but it's the same logic..

Advantages of doing it sooner:. - you stop worrying about it. - you aren't lying to him when he talks about future plans, etc. - he can stop spending money on this proposal, he'll have time to cancel things, get deposits back, etc. - the sooner you tell him, the sooner there is an endpoint from which to move forward

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- It still leaves options 1 through 4 essentially open (although don't offer to stay with him, it's a break-up), but with the benefit of knowing where you both stand, again, no lying, no deceit. After the initial shock, you two can agree on how you approach the trip, together, or separately, or decide who should go and who should sit it out. Given he is currently ready to propose, I have a feeling the last option is best.

ChickenScratchCoffee − Break up immediately. It’s no longer working, pull the bandaid off. He can be mature and go on the trip or stay home. That’s his choice.

joe-dirt-1001 − If you are wanting to break up, then you break up ASAP. Nothing else is your concern.

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Princess-Lacy-xo − I was recently in a very similar situation. It was very difficult but I recommend the last solution. Break it off before the trip and do not go on the trip. That’s the option I chose and it helped him understand how serious I was about the breakup. Best of luck girl 🩷

chez2202 − First of all, it doesn’t take 2 years to plan a proposal or make a custom ring.. Secondly, he should not be proposing when you are there for someone else’s wedding. That’s tacky.. Third, if he isn’t interested in marriage why would he have spent 2 years planning this proposal. Finally, you HAVE to tell him that you know. It’s unfair to let him keep hoping that a ring will fix things. You have already checked out of the relationship. Don’t embarrass him.

[Reddit User] − This is horrible timing for sure, but I think you should consider breaking up with him before the trip. I can definitely see the temptation to simply tell him no wedding talk and go on the trip for his sake and the sake of your friends, but faking being invested in the relationship during the trip would be emotionally exhausting for you and probably cause you a great deal of stress.

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Your partner will likely sense that something is wrong, and can you imagine how terrible it would be for everyone if the two of you got into a big fight and split on the trip? Besides, if you want any chance of having this split be as civil as possible, you don't want him to realize you've wanted to break up for a while and just went on the trip out of obligation and pity. Best to just get it over with so that you can both start to move on.

BitterAd9906 − Tell him before the trip. It's only fair. And then he can decide if he wants to go or not. All of this fussing about getting it right is manipulative (and it's okay, but maybe looking at it that way will help you see that the only way here is to be honest NOW.

Don't wait, it's cruel for both of you). Tell him outright what you just shared: you love him, you're grateful for all these years and all that you've shared, and you're certain that what's best for you is to end the relationship.

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trayC-lou − 1 and 5 are sort of the same, but just tell him before and see what he thinks or wants to do. The trip for him will suck either way if you did or didn’t tell him so please don’t put the pressure on thinking it needs to be or stay an amazing trip for his happiness if he is a depressed anyway

RickRussellTX − You tell him now, and clearly, and bow out of the trip and the wedding. It's the only answer.

TexasLiz1 − TELL HIM! Imagine how you would feel if the shoe were on the other foot and he got to the other side of the world and said “oh yeah - I thought you were too pathetic and weak to go on this trip without me as your boyfriend crutch but I have been planning on dumping your ass for a couple of months now  aren’t you glad you got this trip under false pretenses though?”.

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Tell him. Push for option 5 and let him know you plan on going whether he does or not. And two f**king years to plan a proposal? Jeebus - you will die of old age before he can get his s**t together for even a quickie Vegas wedding.

These Reddit takes cut deep, but do they nail the best path? Is breaking up now the kindest move?

This story of a looming breakup and a dream trip proves love sometimes means letting go. Her resolve to end things, despite his proposal plans, prioritizes honesty over comfort. Reddit leans toward ripping off the bandaid, and she’s poised to do just that. So, readers, what’s your take? Would you break up before the trip or wait it out? How do you handle heartbreak with big plans on the horizon? Share your stories below and let’s keep the convo rolling!

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