I am desperately asking for your help….ANY help. I am planning to propose to my girlfriend of 4 years next weekend (February 15th). We are long distance and I am flying into Chicago on the 14th. I got us a hotel room downtown but cannot think of any really great ideas.
Please don’t assume that I’ve waited until the last minute. I’ve been scouring ideas and trying desperately to come up with something for months.
Several problems I’m facing:
1-It is insanely cold…outside for too long would be tough
2-Obviously it’s Valentine’s day so almost everything is booked up
3-I don’t really want to propose in a restaurant in front of a bunch of people
4-Though I am not incredibly familiar with Chicago…I don’t want to do anything too incredibly “tourist-ish” (McCormick Building, Sears Tower, Navy Pier, etc.)
Again, please…any help or small ideas (or big ideas) would be greatly appreciated.
I wouldn’t do it on Valentines Day at all – too cheesy. I would do it the morning of Feb 15th, and have breakfast delivered to your room and have breakfast in bed. You could have the ring on the tray, or you can just have it and get down on one knee by the bed. Something along those lines. And then you can celebrate all day long as a newly engaged couple. You’ll probably be able to get a reservation for that night somewhere. It doesn’t need to be something elaborate, just something sweet and simple!
My partner had planned a picnic with a view to propose (one of my fav things to do) and the weather turned UGLY.
He booked a night at a five star georgous hotel room with a fabulous view. He had champagn and had bought seafood etc for a picnic there instead 🙂 I had NO CLUE he had planned this – all I knew was the massages prior and dinner after which would be a surprise…when we got to the hotel initially I thought we were eating in the restruant and when we went up the elevator I thought he was thinking a ‘naughty’ night away from home 😉
It was perfect – no bunch of ppl watching, intimate and exactly something I love doing – eating a picnic and staying in a fancy hotel!
What if you did something just ultra romantic but low key… like wake her up and lay on top of her kind of thing and have her close her eyes while you tell her all the things you love about her, (I saw a scene in a movie once where he said to the girl something like “you are exactly where you are supposed to be. You are exactly who you are supposed to be. You have nothing to worry about because in this moment, you are perfect” – and he wasn’t proposing)… anyways, I would think a super intimate, private moment like that would be sweet, and when you tell her to open her eyes, you have the ring box open between you ….
then have roomservice breakfast in bed and simosas (sp?) – get couples massages, take her to see a play or something, a romantic dinner… I’d propose early on so she can enjoy the whole weekend together as an engaged woman!
I also wanted my proposal to be private – if my FI proposed to me this way, I would be on cloud 9
The proposal I wanted and didn’t receive is straight out of the movie Stepmom. Tie a string around her finger while she is sleeping and when she wakes shimmy the ring from a distance down the string. I love the simplicity and playfulness of the proposal. Plus it’s very private.
Or you can enlist the hotel staff to add roses and candles to your room. As she oohs and ahhs over the romantic spectacle you can get on one knee to propose.
The problem is that the hotel is not super nice. (…long story. She lives South of the city in Hyde Park and had got us a room at MileNorth just for a night…Valentine’s day). I just extended the reservation for the whole weekend since I knew in my head I’d be proposing.
I don’t think the Hotel has room service, etc. It’s right in the heart of the city…but certainly not a five-star hotel. I might be able to get a bottle of wine or champagne delivered, doubt much more.
…I agree, I don’t want to do it on Valentine’s Day either. I think Saturday morning would be best.
I like the idea of suprising her in bed but feel like she would never forgive me for not being able to brush her teeth first. ha.
Anyone from Chicago…you think outside would be too bitter cold??!
@Snd297: Do you want it to be private or romantic? If you want to make a twist on the whole valentine’s day thing then maybe you could do it at Cupid’s Undie Run??? lol. It would be humerous if you think she would take it well. It would be memorable! You could even see if you can get ahold of event coordinators to see if they can help you plan it out.
Chicago is also having a Valentine Zombie event. What’s more romantic than being scared out of your mind, playing lazer tag with zombies then popping the question? Ever notice how in scary movies, they always find time to kiss in the middle of being hunted? lol. You could tell her that you promise to protect her forever, from zombies and all! 🙂 Lol.
@haker4: haha, I think if I did that than she would flat out say no.
We are both very, very boring and simple. I don’t think it necessarily has to be private,…but I am hoping to make it romantic and serious enough that she remembers it forever.
We’ve been together four years but are now doing long distance for the first time. She started law school this past fall and I have to finish my residency before I look for work in Chicago. She’s been my rock through the illnesses of both my parents and all my own years of schooling…..I just don’t want her to be disappointed.
Thank you for the links. Thank all of you for your help and insight. All of these ideas are great…I should have found this site and posted a long time ago.
@Snd297: I was going to say have a drink on top of the Hancock during the day. Wooo views. But if you don’t wanna have a public thing that’s out. Still fun though! You should just speak from your heart. And if you do propose in the hotel don’t forget to get down on your damned one knee (May or May not have happened to me….).
It might be cold out, but if you walk down by the museums (planetarium), there is an awesome view of the skyline and the water. It’s not too crowded, but it may be windy and cold.
oh oh! Or take one of those horse drawn carriages and pop it on there! i always see them near michigan avenue!
@Snd297: according to the weather channel, it is supposed to be 22 degress the day after valentines day (which is much warmer than it has been lately lol). as long as you dont stray too far from restaurants, etc. you could always propose outside and then make reservations at a nice restaurant. personally, i would do it outside because the view is amazing 🙂 you dont have to stay outside that long especially if you arrange for a cab beforehand
“the Field Museum of Natural History might not seem like the obvious place to propose, but they do have a very novel proposal package which might be worth considering. At the updated Grainger Hall of Gems, which houses diamonds and gems from all over the world, you can place your engagement ring inside a dedicated exhibition case within the gallery with a personal message and special lighting. You can then celebrate at the museum with a champagne toast.”
I’m not sure how much it costs but it’s inside!!!
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