(Closed) I need advice for surprise proposal in Jamaica!

posted 5 years ago in Proposals
Post # 3
11271 posts
Sugar Beekeeper
  • Wedding: April 2012

@XELOR:  not many people are going to be dressed up at noon.  she may get suspicious.  is there any way you can change the photographer to 5pm or later and tell her that you are going to a fancy restaurant for dinner?

Post # 5
719 posts
Busy bee
  • Wedding: August 2014 - South Bonson Pier & Community Centre

@XELOR:  I really don’t think she needs to be wearing heels, but maybe just say “hey, lets go take some pictures (here)” which will tell her that you’re not going down just to the pool. Are you thinking these are going to be your formal engagement photos, or just photos of the event? 

Post # 6
4933 posts
Honey bee
  • Wedding: August 2013

I agree with 


Set it up for dinner. 


If you can’t, tell her you booked a fancy wine tasting excursion or something and you need to be dressed up. 

Good luck 🙂

Post # 7
1938 posts
Buzzing bee
  • Wedding: March 2014

Step 1: Casually mention that so and so from work went to that resort and recommended some amazing restaurant and you need to get the name 

Step 2: Tell her after you get to Jamaica that you got the name of the restaurant but they don’t have any dinner reservations open but they do have a lunch.  Ask her if she wants to try it out, but don’t seem invested in her answer.  If she says yes, see step 3A.  If she decides to pass, see step 3B

Step 3A:  Pretend to call the make believe restaurant and set up a lunch reservation.  Make it obvious this is a sort of fancy foodie place and you’re not going to wear your bathing suit shorts.  Proceed to location for proposal

Step 3B: Crap.  Guess you will have engagement pics in casual gear. Worse things have happened.


Please note this plan only works if you both actually care about good food/ trying new restaurants AND you play it cool and make it seem like it just sounds fun to try and not like you must do it.  Otherwise I got NADA in terms of suggestions 🙂

Post # 9
12 posts

Can you do it another day?


If not, I agree with Andthepupmakes3, say there is an event, and ask her to wear something like a sundress if thats fancy enough for you, and go a little more casual on your part.

Post # 10
563 posts
Busy bee
  • Wedding: June 2014

@Andthepupmakes3:  Agreed. I’d stick to the fancy restaurant that only has lunch reservations and tell her there’s a dresscode. 

Post # 11
1006 posts
Bumble bee
  • Wedding: February 2014

Will she see the photograher there or is he hiding or something? If she will know there is a photography can you say you want to dress up for a photo shoot of your vacation? Otherwise, I agree with other posters. Say you are doing something that you need to be dressy for.

Post # 12
229 posts
Helper bee
  • Wedding: May 2015

tell her that you are taking her out to dinner at a really fancy place but there won’t be time to go back to get changed, so you both have to dress up earlier in the day.  Then say we have an appointment to go take a tour at noon.  The two little lies will be worth it once she has the ring on her finger.  Congratulations!!

Post # 13
750 posts
Busy bee
  • Wedding: November 1999

You can go out buy her a new dress and leave a note in the shower when she is getting ready saying something along the lines of that you have something special booked. I would do outside excursions in the morning (nothing that will make you sweaty or dirty – perhaps some shopping and brunch?) and then come back in time to the beach and pop the question.

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