(Closed) How not to let engagement hopes overshadow our summer vacation

posted 6 years ago in Waiting
Post # 3
2087 posts
Buzzing bee
  • Wedding: October 2014


I was with my Fiance almost 4 years when we got engaged.  Similar to you, we’d discussed it many times, I knew we were on the same page, but I was starting to get really ansy.  He was (and still is) in school and said it wouldn’t be til the end of 2013 at least because he wanted to be done school and working before he got a ring.  I felt sad but understood. 

But last spring, on a road trip together I was looking for a pen in his car and found cards with quotes from jewellers in the console (he quickly closed it and said there was no pen in there) lol.  However, I dropped him off at a hockey game and then ransacked his car and found and read all the quotes. 

We had a fancy dinner coming up the next month at the CN tower to celebrate our quitting smoking and began to think he’d do it then.  I hate to admit this, but I even looked at some of his banking and saw he’d made a large deposit at the jewellers.  I totally ruined my own proposal.  I knew when he bought a new suit for dinner that he would be doing it that night. 

Part of me still told myself he might not do it and don’t get my hopes up, but he proposed right before we went up for dinner. 

I guess my point is, it’s ok to be excited, but if you over think it, you’ll ruin it either way.  Either he’ll propose and you wont really be all that surprised because you’ve played it out in your head as happening there so many times, OR he won’t propose and you’ll be disappointed and not really enjoy your vacation. 

If I could go back in time, I would’ve forced myself not to look… to let the surprise come when he was ready.  He still thinks he blew me away with that proposal, but the truth is I’d known for over a month the exact night he was going to do it, and that kind of sucked.  |Even though it was a very sweet proposal 😀

Post # 4
2087 posts
Buzzing bee
  • Wedding: October 2014

I guess one perk if he DOESN”T do it on vacation, is then it really will be a surprise because you’ll have no idea when or where he might do it


Post # 7
2389 posts
Buzzing bee
  • Wedding: July 2011

Um, talk to him about it? This is your life too. He shouldn’t have all the control.

Post # 8
2087 posts
Buzzing bee
  • Wedding: October 2014

You know, if you really want to take the wonder out of it, you could always ask him NOT to propose there… tell him it would be a little too predictable and you would rather he do it some other place.  Then you really can relax when you’re vacationing there

Post # 9
3152 posts
Sugar bee
  • Wedding: May 2018

@MsMonkey:  so easy to make yourself crazy! My SO and I are headed to Belize in 3 weeks and tho I don’t think it will happen its kind of kicking around in the back of my head. same as you I don’t want to ruin the trip by expecting it & being disappointed. Tho you don’t want to ask to much and ruin the surprise! Maybe ask for a general ‘will it happen this year???’ kind of timeline?

Post # 10
52 posts
Worker bee
  • Wedding: October 2013

Hi, I was in a similar situation.  At our 3 year mark we went on a very romantic cruise and I was convinced he was going to give me a ring.  I even started googling “romantic ideas to propose on a cruise”.  I knew we were going swimming with dolphins and found great proposal videos of the dolphins going below and getting little containers with the rings.  I built up the whole engagement in my head lol and you cant even imagine my disappointment when the trainer told the dolphin to “go get a rock”……it was a seaweed covered rock rock… I didn’t get my ring then…..then I did the same thing a year later when we went to the redsox opening day, then again at the 100th anniversary game No ring….after that I made the decision not to think about it.  And when the day came last September and he caught me completely by surprise with a an unbeleivably perfect and yet unexpected proposal it made me so happy he didn’t do it when I was expecting it.  I also have a friend who pressured her boyfriend (now husband) and figured out the date, place and saw the ring and she told me how she wishes now that she had been surprised.  so don’t let it ruin your vacation (believe me it isn’t worth it) just enjoy and maybe he will or maybe he has an even better plan 🙂 best of luck and well wishes 

Post # 12
111 posts
Blushing bee
  • Wedding: October 2014

we are going to the mountains & staying in a cabin for about a week for our anniversary this summer & I too am hoping for an engagement!!! It will be our 9 year anniversary, so Im getting anxious!



we’ve lived together for 5 years (started dating at 15 & 16) or I honestly think it wouldve happened sooner

Post # 13
4523 posts
Honey bee
  • Wedding: September 2014

@MsMonkey:  girl, when you figure it out let ME know: we are going on vacation in August and I”m pretty sure thats ALL i’ll be able to think about.

Post # 14
1105 posts
Bumble bee
  • Wedding: September 2013

I was in the same boat, we went to Japan and before we left I wondered how on earth do I keep my hope about him proposing, in check, and if he doesn’t propose, to not let it ruin our holiday?

Well I can’t tell you what I did because he ended up proposing 5 days in :). But knowing me I would have cried on the last day of the holiday and made a big deal out of it… soooo glad that didn’t happen!!

Fingers crossed for you!

Post # 15
532 posts
Busy bee
  • Wedding: June 2015 - Backyard

If you figure it out let me know too…we are planning on getting engaged this summer, he promises me he wants to marry me and has said that it will happen this summer, our 5 year anniversary is in June, I have 2 10-day stretches of PTO this summer and planning to go out of town for both of them, so there will be plenty of romantic opportunities…but I’m already a bit anxious about how I’m going to keep from bringing it up / hoping for it to happen and I honestly hope he does it before all that or at least on the first trip so that I can relax and enjoy my time off! I haven’t had a real vacation in about 8 years (been in school then grad school and working full time since I graduated high school) so my PTO is sort of precious and amazing in and of itself, I better enjoy the heck out of it!

Anyways, I’ve already failed at not bringing it up by making little comments about getting engaged in the past couple of weeks….now that it’s mid March and I potentially only have 3-4 months left of waiting I really need to shut it up!!!

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