Dan and Carrie are your classic modern day romance story... a mutual "Like" on the Hinge app turned into a love neither of them could have expected. Carrie was shocked when Dan asked her to dinner for their first date, as she'd historically only been open to drinks or coffee to keep them short just in case it didn't go well. She swore to her friends this was her last Hinge date, and she would afterwards delete the dating apps forever. Dan on the other hand was new to the world of dating apps, felt out of practice and nervous how he'd do, so had no idea what to expect. Any nerves or anxiety vanished the minute Carrie walked in and approached Dan at the Siena Tavern bar. There was an instant comfort to each others' presence and what started as maybe only a few awkward hours out on a Friday night turned into neither of them wanting it to end. They talked at Siena Tavern for over 5 hours, only leaving when they decided to go for an adventure and find a hidden Speakeasy they both had been wanting to check out. They continued to talk as if they'd known each other for years until the bar closed and kindly asked them to leave so the workers could go home. It was hands down the best first date either of them had ever had, and they both went home with a strange feeling it might be their last... turns out, they were right!

Dan planned a walking tour of one of Carrie's favorite holiday traditions - visiting the biggest and best Christmas trees in downtown Chicago. She was under the guise that they were meeting friends later on for dinner. Of course at the last minute, Carried tried her best to change the plans as she thought she had a better, more efficient itinerary. With some clever quick thinking, Dan calmly adjusted without tipping her off. Dan proposed on the Millennium Park terrace - a moment captured perfectly by a photographer he had there in-waiting. After the proposal, both sets of parents, siblings and a collection of closest friends were waiting close by at The Gage to celebrate! It was the surprise of a lifetime for Carrie, and a day neither of them will ever forget!