Like many millennials, Jenn and Dan first met on a dating app – in their case, it was Bumble. Jenn came across Dan's profile, which said, among other intriguing details, something to the effect of "lawyer - snowboarder - singer - guitar player - improviser". Jenn's interest was piqued by Dan's profession (the same as hers), that he graduated from a Big 10 school (just like she did), his variety of hobbies (since at the time – and let's be real, also now – her own hobbies included primarily spinning and brunch and not much else), and that he was from Wisconsin (a Midwestern gent), so she decided to message him with a winning one-liner that started it all: "Tell me more about this lawyering, singing, guitar-playing, improvising unicorn!"

As Dan had just moved to Chicago for work the month before and was still getting familiar with the city, Jenn suggested a quality spot convenient for both of them: Siena Tavern, a River North neighborhood staple. Jenn arrived that evening in her fall first date uniform – tight black turtleneck sweater, dark skinny jeans, and booties – to find Dan waiting for her at the bar in usual man attire of a button down shirt and jeans. She was immediately struck by his sweet smile, bright green eyes, and friendly demeanor. They decided to sit at the last open table in the bar area, tucked in a corner against the window, where they’d better be able to focus on each other. What was supposed to be a meetup for drinks turned into dinner as they enjoyed their conversation, which flowed easily and covered topics beyond the usual first date go-tos, and each other’s company. Both were surprised to discover a few hours had flown by, and they parted for the night with the promise to see one another again soon (spoiler alert: they did!).

As usual on summer weekend mornings, Jenn and Dan went to brunch in the neighborhood – on this day, they chose the Barrio patio. They planned to head directly to Macy’s afterward because it was Macy’s Fourth of July furniture sale and Jenn was set on going to look for a couch for their new place – she couldn't miss out on the discount! Dan suggested taking a leisurely detour to Macy’s with a walk along the lake since it was such a beautiful day. Jenn made some grumblings about doing the walk after couch shopping, but since it was early and she was already prepared for a walk in the blistering heat in her workout outfit, sneakers, and ponytail, she agreed. Jenn was oblivious to Dan’s grand plans upon reaching Buckingham Fountain, a favorite destination of theirs, where he suggested walking before backtracking to Macy's. Jenn thought getting sprayed by the fountain water would feel fantastic in the heat, so she told him it was a great idea. Upon reaching the fountain, Dan and Jenn put an arm around one another and stood in the refreshing spray. Then Dan said “Guess what?” Generally when one of them asks this question, it follows with a “you’re cute” or an “I love you”, but this time Dan said “I have something in my pocket” (!!!!!). As Dan got down on one knee, Jenn looked around wildly, blinded with tears and fountain water, making unintelligible sounds of happiness as she realized this was actually happening! After Dan proposed and Jenn responded with an emphatic “of course I will!”, a congratulatory bicyclist passing by insisted on giving them a photoshoot in front of the fountain to memorialize the moment. Dan and Jenn spent the next several hours FaceTiming, calling, and texting family and friends with the happy news before eventually making it to Macy’s to couch shop. They celebrated with dinner at Siena Tavern that evening, complete with pizza, pasta, and a sparkling toast at the exact same table where they had their first date.