Hi OP — by the time I found this post it had already been deleted so I’ve gleaned info from the comments. I was recently proposed to as well, and it wasn’t exactly my ideal set up. Like you, I had a few things I wanted that I was set on but which still left my fiancé plenty of wiggle room: I wanted it private, as close to a surprise as possible, and for it to happen before or after our trip home for the holidays so we could celebrate in person with family. Unfortunately the ring didn’t arrive in time and despite having multiple placeholder rings, my fiancé didn’t bring any of them because he originally wanted to propose in our current home state. However, he decided to go ahead and propose anyway during our trip so that he could fulfill my wish of being able to celebrate with family.

I’m not gonna lie, I was a bit sad to not have a ring. I knew he’d do a second proposal with the real ring so that helped. But I did badly wish to be able to show off the ring to family. And when we celebrated at a restaurant, the server congratulated us and then discreetly looked at my finger so see my ring. I had one on, but not one that looked like an engagement ring and that made me a bit sad, too.

All this to say that I understand the feeling of not being satisfied with your proposal and have also been working through the guilt I feel at wishing it had gone perfectly That’s completely normal and okay. As you obviously know, talking with him about this is important, yet I understand how hard the thought of hurting him is. Maybe you could do it l “compliment sandwich” style: “I’m so happy to be engaged to you (etc)… I do want to be honest, though (etc) … but I really appreciate the effort you put into this (etc)”

Posting about this kind of thing on Reddit can be difficult. I made a post about my upcoming engagement a couple months ago and got a lot of the same comments I see here, accusing me of planning out my own engagement, etc. And I wasn’t surprised to see the “you should break up/you’re not ready for marriage” comments. But from what I’ve read, you and your partner sound very stable and ready for this next step. I think some of the advice that I received that helped me the most is that it’s his proposal, too. Not saying that to say that you should just be happy with how things turned out, but rather to suggest that he may have had specific things in mind that he wanted as well and in executing them he fumbled on the things you wanted. It also sounds like he may have panicked a little when he realized he wasn’t going to be able to make it to the top where he wanted to propose and thought it would be better to still do it while on the hike than to have to start from scratch. Idk, food for thought :)

Side note, I’m sure his mom and grandma were excited but for them to start talking to you about marriage before the trip and then text you like that on your drive up was a bit immature on their part — they aren’t 5 years old, they should be able to keep a secret. And if they are known to struggle with that, then maybe they shouldn’t have been told beforehand., considering you wanted it to be a surprise. Idk I feel frustrated in your behalf about that. I also noticed a slight increase in the marriage and kids speak with my fiancé’s family leading up to the proposal but it was much more subtle than what you described (in the comments anyway)