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Vacation Proposal: When to pop the question?


Mar 1, 2011
Okay, so some of you may know that I picked up a Tiffany Solitaire for my girlfriend a few months ago. Well, I've been waiting to propose until we are on our Florida vacation coming up in a few weeks.

I've been thinking about when I should actually propose. I know I want to do it on the beach, probably at sunset.

Here is some background info:
She knows the proposal is coming within 6 months.
It's a guaranteed yes.
Our vacation is 8 days long: 4 days at one place, 4 days in another.
Both resorts are located on the beach.
We arrive on a Friday afternoon/evening (around 4-5PM)

So, when should I propose?

I'm thinking either the first night (however, I don't want things to be rushed and this could cause it to be less relaxing and romantic). Or perhaps, the second night (that way we can be settled in, have spent our first day together, and then go out to a nice meal either after or before I propose.

What does everyone think (I especially would like to hear from the ladies)?

Thanks much all!


Oct 30, 2007
Do it ASAP. I guarantee you will be acting weird and it will freak her out, or at the very least make for a less pleasant day.

My BF knew it was a 100% yes but he still was acted strangely the whole day, being nervous and preoccupied. It will happen to the best of men! Good luck, and don't make her wait longer!


Mar 30, 2011
Congrtulations on the impending engagement. I think you should play it by ear but do it within the first few days. I agree that the first day may be too stressful. Keep the ring with you and when the moment feels right on day 2 or 3 go for it.
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