an overplanner needs help rescuing proposal ideas

[warehouse1990]

i''m planning to propose in 2 weeks. i have had tons of ideas, but i feel like i have overplanned everything and will not make it enjoyable enough.

We live in Stamford,CT, which is about an hour from NYC. I moved to Conneticut (from NYC) for us and to really see where things would go. Well, they are headed to the alter. I have told her that I would like 3 dates in early June.

I have been leaning to proposing in NYC, as it is where we meet. But, there is a part of me that has thought about doing this all in CT. Anyways, my idea is as follows (feedback is welcomed and needed):

We would drive into NYC, park the car, drop off clothes at her mother''s house (she lives there). We would then jump in a taxi and goto Loeb''s boathouse. We would rent a rowboat, which is where I would propose. But, then we would jump in a cab and goto her father''s house to show him the ring. Then we would go back to her mother''s place (yes, parents are divorced, but good friends). We would then change into fancy clothese. We would then move the car and drive it near a fancy restaurant, i''m leaning toward the Four Seasons or Cafe Des Artistes. Have a nice dinner and then drive back to CT.

It just seems like a lot and seems like we are under such a schedule. I want us to be able to enjoy the moment. Also, I am concerned about rain.

I have had other ideas, like proposing at our apartment in CT by having a lot of candles and flowers. And then driving into the city. Sure, we would build in time with her family. I have also thought about doing it at the carousel in Central Park, where she went as a kid.

Part of the stress is that she is a teacher and has a lot to get done by the end of the year. In the same token, she would like to get engaged before the end of the year and show the kids.

Help!!! Am i overplanning? What ideas do you think is best? Any other suggestions?

Craig

 

[adillus]

Can you save some time and driving around by having her parents meet you for dinner?

 

[AtlantaC]

If I were you, I would slim down the schedule a little bit. Your narrative makes it sound like a two-day event. The boat idea sounds really cool, and I like the last poster's idea of having the parents meet you for dinner later. It's possible though that your story indicates that her parents aren't together, so that might be out. In any case, there's a lot to be said for planning up to the moment, but then letting what happens after be organic and unplanned.

 

[Judi W]

You said it yourself - "I'm an overplanner". You have a good plan with the rowboat, and even if it rains - a rainy day can be romantic. Have an alternative "dry" place picked out. But sometimes a bit of spontaneity works best. Relax...it'll all work out perfectly and be a moment you'll both treasure!! All the best.

 

[verticalhorizon]

That definitely sounds like a logistical nightmare. You don't want to have to worry about anything on your proposal day... other than the proposal itself that is.

I say, boat idea=good. Dinner idea=good. Meet up with the parents somewhere all together on Day #2. You guys need time to relax and be in bliss together for at least one day! Parents will understand.

PS: Don't drop the ring in the water!

 

[warehouse1990]

thanks for all of the responses.

the reason i had thought about initially stopping by her mother's house is to drop clothes off so that she would believe that we are staying overnight, ie suprise her.

however, i could possibly park by the boathouse and restaurant and we could then head uptown. i could just tell her that we will take the stuff clothes to her mother's afterwards. In all reality, after the boatride, we would still take a taxi and change of clothes uptown. Or i might look into having us change elsewhere like a few friends that i know.

as far as visiting the parents. my thought is that the last boatride at Loeb's is at 5 pm ( i need to verify this it maybe later). We have an 8 pm dinner reservation. Hence, time in-between to visit the parents if she so desires.

i still feel like i'm overplanning though.

Craig

 

[verticalhorizon]

You're right, still sounds complicated. It looks like you're going all out already, go to hotels.com or one of those other sites and find a modest place to stay that one night and cut out all the clothes carrying/driving around. It will make it seem less like work and more enjoyable. Meet the fam the next day and keep your day to yourself.

That's just my opinion. Good luck!

 

[warehouse1990]

thanks. actually, i have thought about it quite a bit and am going to simplify things significantly. There maybe still a boatride and will definately be a fancy dinner, but i really thought about this and thought about us and what is special to us. So that is what i will go with.

i'll let you know how it went.

Craig

 

[abeawasthi]

Good luck! I definetely second the boat idea!