Another Chicago Proposal!


Aug 4, 2011
Hello Everyone.

Yet another Chicago proposal thread! I've searched the other threads and gotten a pretty good idea of what I want to do. Problem is, I live in Houston and I'm not sure how feasible my idea is due to weather/concurrent events/etc. Let me know what you think of the following:

Has to be a weekend in October, preferably a Saturday night.

Before: A fun day, then nice dinner downtown. Throughout the day I will find myself on one knee (falling, walking up stairs, tripping on a curb) to get her hopes up but end up ring less each time. I've already started to do this to throw her off guard :twisted:

Around sunset we head to the Navy Pier area as it is close to our hearts. I'm thinking the end of Navy Pier or in Jane Addams Park, PFC Oliver Park, or Navy Pier park. Somehow I want to have a bench/table/picnic blanket set up nicely before hand, but not in view (her friends can help). We will walk near the spot, talk for a bit, then at the right moment I'd like to have a violinist start to play our favorite songs and draw us to our special spot which will then be lit with candles (again her friends could help). Cue speech, ring, then live happily ever after, etc etc.

- WEATHER! Will it be too cold? We can tough it out if it is not too bad.

- HALOWEEN! Navy Pier has the Haunted House thing, I'm afraid the area will be crawling with families/kiddos/teenagers.

- SUNSET! I think the parks close at sunset, so we wouldn't have much time to enjoy the moment. Navy Pier will be open but might be too busy. Can we get special permission to use the parks after hours?

- VIOLIN! How would I get a decent violinist, how much would it cost, and would they be willing to sit outside in the cold? I might put up a listing on craigslist and see how it goes. Could do some other instrument, or just have a boombox at the very least. Maybe having another person around might be odd, especially if her friends are lurking in the distance. But they could take video/photo!

- TOO MUCH?! It might be a bit over the top for some, but we've done so many romantic things on normal dates that I have to go all out. Plus she totally deserves it :bigsmile:

Well that's all I can think of for now. Let me know what you all think and what I've forgotten.



Jan 18, 2009
I can't answer all of your questions, but with regards to weather, it should be too bad. Maybe between low 60s in the day to mid 40s at night. Maybe rain, but maybe not. It's not going to be miserable though!


Jun 29, 2011
Signature Lounge? Such a pretty view there.
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