Proposal Help in NYC - Hotel or Central Park?


Apr 4, 2011
Hi everyone,

I finally have everything set for my proposal except for 1 thing - I keep going back and forth with when to actually propose. This is everything as I have planned out so far: (comments are welcome!)

I've convinced my girlfriend we're going on a roadtrip over the weekend (we're in Toronto driving over to Montreal). I also asked her to bring her passport because there's some camera store just south of Montreal in the US that I want to check out. These are all lies of course. What we're really doing is flying over to NY and staying 2 nights at Sofitel hotel which has received outstanding reviews.

I've also bought premium seats for Wicked which we saw in Toronto and she absolutely loved. She always asks me every now and then if we can ever go to NY to watch it so I'm positive she'll be thrilled.

Now comes my dilemna. I cannot decide between the following 3 options...

1) After checking in, we'll head over for dinner where I'll surprise her with the Wicked tickets. At the same time the concierge will be making up our room with rose petals, candles, wine. She thinks the Wicked show is the main surprise so when we return to the room and I propose she'll be really shocked.

Pros: I like this plan since it really compresses everything to really surprise her with things happening one after another.
Cons: I'm not sure how she'd react... would it ruin watching the musical? Also, I want pictures of her reaction but not really possible in our room.

2) Same as above except instead of proposing after dinner and before Wicked I propose after Wicked. Kind of to top of the night - from starting the day thinking we're going on a road trip, to flying to NY, watching Wicked and then finally being proposed to.

Pros: She enjoys the day, enjoys the musical, and I save the best for last.
Cons: Wicked ends around 10:30pm, so back to the hotel around 11pm. Is there such a thing as too late? Maybe she's tired after a long day too?

3) I wait until the next day (Sat) and propose at Central Park. This will either be on the boat by the boathouse or while having a picnic.

Pros: She enjoys her first day and I think the park would be romantic. I can hire a photographer to take hidden pictures of the proposal.
Cons: Will the park be packed? Sat in August during the day.. I know she wouldn't want a very public proposal.

So here's my dilemna! Thanks in advance.


Jan 18, 2009
My understanding is that guys tend to just want to get it over'll probably be a bit nervous/excited..if you think that is going to be the case, then I'd say do it as early as possible...either after dinner / before Wicked or even right when you get to NYC. She might be suspicious anyway with the other surprises.


Jul 22, 2011
I wouldn't do it before Wicked as I think the engagement will overshadow the show and from my personal experience the minute you get engaged all you want to do is celebrate/ring friends and family/have a few glasses of bubbly/get excited etc etc etc..

At the same time I agree with centralsquare above - most blokes just want to get the deed done and kick back - is there anyway you could change Wicked to the second night of your stay in NY, then propose in NY the first night before dinner? Catch her totally off guard maybe go for a wander in Central Park after you've checked into the hotel around early twilight (really good time for photos BTW - and if you're going to hire a pro to take some secret shots the lighting will be gorgeous at this time of the day - and there may not be as many people around).

Plan a bottle of bubbly back up in the hotel room which you can head back to after you've popped the question to enjoy together before dinner. This also means you have a bit of time to yourselves after the excitement settles down a tad (call folks/mates etc. if needs be) then you can head off for a dinner and drinks at a swish restaurant both feeling on a high, knowing you've a night together to celebrate and enjoy the moment - she'll be a super excited, dressed up and you'll be the same and a tad relieved ;-) Then you still have Wicked to look forward to the following evening.

That would also mean she (and you) get to spend her entire surprise weekend in NY whilst newly engaged - if you know what I mean?


Apr 11, 2010
I'd actually vote for after dinner and before Wicked. It'll be so exciting for her given she loves the show. She'll be on cloud 99! I can't really say why I just know if it was me I'd prefer to be proposed to prior to the show.

Also, I saw Wicked on Broadway and it is utterly MARVELOUS. She will go bananas! What a wonderful partner you are!


Apr 4, 2011
Thanks everyone for the comments!

Unfortunately I can't move the date of the tickets as they are already bought and paid for. After taking into consideration the timing between what time we get to NY, dinner then the show, I've decided to propose after the show. I plan to have the room decorated while we are watching Wicked and then proposing when we return to to the hotel.

I totally agree that I'll be a nervous wreck all day - I've already been getting nervous a week before and have been constantly checking the ring again and second guessing everything - but I think the timing just works best doing it after.

It'll seem to her that the show is the highlight of the night (and probably weekend) so it should come as a total surprise when I actually propose.

Is it better to have the proposal be a complete surprise or should I let the anticipation build a bit?

As I've planned it right now it should be a complete surprise. Even though it might seem obvious to some of you what will be happening, she's a very sweet and innocent girl so I'm sure she'll believe that Wicked is the highlight of the trip :saint: . I can change things a little bit to help build up some anticipation. She loves getting hints with her surprises so I can find a way to drop hints that there's "more to come".


Jun 8, 2008
I vote for complete surprise and to propose in the park. I might be a bit biased though as when my dh proposed it was a 100% complete surprise and it was in the park. :bigsmile: It was a perfect beautiful proposal. Is there any way you could propose in the park the day you get to NYC before dinner and before Wicked? That way she can take it all in during dinner and hopefully enjoy the show. My favorite broadway musical btw. Congratulations and enjoy!


Nov 18, 2010
Central Park has so many beautiful places to propose. Picnic in Shakespeare gardens, bow bridge, belvedere castle, on a gondola near the boathouse are just a few examples. I also love your idea of hiring a photographer to snap pics of your special moment. And the best part is you could even keep the fact that you hired a photographer a surprise and have them displayed on your wedding day. Wicked is amazing! Its def one of my favs ! :)

Shane Co.

Feb 11, 2011
This is such a great proposal idea! I have to agree with some of the previous posters. Central Park has some very romantic spots. I actually got married at the Bethesda Terrace, and I have to say that it was utterly gorgeous. If you want to check it you, you can check it out here:

It sounds like you've put a lot of thought into this and adding seeing Wicked (which is fantastic on Broadway btw) is the icing on the cake. Good luck and congratulations!
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