How Ty Popped the Question!

Wedding Wednesday:

So, I just realized that even after a month of wedding posts I never told you the WHOLE story of how Tyler proposed!  Well – Here it is 🙂


For my birthday, we planned a romantic getaway to the Windy City to see the sights, hit up the shops, and dine like we’ve never dined before. After a chilly Friday night ice skating in Millennium Park, dining in a fancy restaurant, and getting into The Roof of The Wit Hotel for free (& enjoying one too many cocktails), we endured an even colder Saturday morning strolling Michigan Ave.

Later that afternoon we found ourselves back in the hotel room frostbitten and worn out. We then proceeded to buy an $8 bottle of Barefoot Moscato and head down to the hotel lobby to play checkers and chill in the grand leather furniture. Eventually we decided it would be a good idea to grab some grub so we headed to an Irish Pub for an authentic meal (because I had a coupon, of course), and afterward headed back to the hotel. After 30 minutes of debate on what to do next, we called a cab and ended up at The Cite…70+ floors above the city.


The restaurant was decked to the nines with floor to ceiling windows, a stunning view of Chicago, the finest of dishes & wine for company, and goers with shoes that cost more than my whole wardrobe combined. Anyway, we were seated at a table for two and ordered a fancy bottle of wine (because hey, we’re on vacation). Not even two minutes later Tyler said, “I have to go to the bathroom,“ and I said, “go for it, sweetie.” A few minutes later the waiter came by and told us the wine would need some additional time to chill and to just sit tight for another 10 minutes. We were happy to wait because we were definitely not in a hurry to escape the amazing view and, let’s be honest, there’s nothing worse than warm white wine.


About 10 minutes later the waiter returned to drop the wine off at the table…then walked away. “How rude,” I thought to myself once I noticed that the cap was still on the wine. Then I did a double take. Tripple take. Could that be, is it, no…that’s just one sparkly freebee. Nope – that’s no freebee, THAT’S AN ENGAGEMENT RING! Before I knew it Tyler was on one knee (taking nearly the whole table cloth with him) and proposing right there in the middle of the restaurant! Of course I said, “(heck) yes” and the rest of the night was full of toasts, laughs, super fancy cheese, and spirits.

(((Later that night I discovered why he seemed so nervous to use the bathroom…It was because he had given the ring to the host to tie to the neck of the bottle of wine we ordered. How sweet ❤ )))



What’s your dream way of being proposed to?  Or, if you’re already engaged/married, how did he pop the question?


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