To start, it was a miracle that Blair even made it to the first date. They planned to meet at a bar near Blair's apartment in Lakeview called Barcocina because Blair loves spicy margaritas and that is their specialty. Blair had celebrated her birthday the night before and therefore was moving rather slowly, so she asked if they could push the date back a couple hours. Bryan gladly agreed and in a supposed effort to "get to know the city" decided to walk the 2.5 miles to Barcocina from his apartment in Gold Coast. Unfortunately for Blair, she did not factor in the possibility of the Pride parade running long and blocking the streets surrounding her apartment (even to pedestrians!), preventing her from getting to Barcocina. Instead of cancelling, Blair picked a new spot near Wrigley that would hopefully be easier for her to get to. Blair ended up walking over a mile north to get around the parade and located the very tall red head waiting for her outside of Wrigley Field. By the time they sat down for their date, it was over 3 hours after the original date time. But despite the logistical nightmares, the first date led to a second and third date in rapid succession and the rest is history! (Bryan will also tell you that Blair took her sunglasses on and off about 20 times during their first date, but Blair will vehemently deny that any such thing occurred.)

Almost three years to the day of their first date, Bryan had planned to redo their first date by actually grabbing drinks at Barcocina, the bar where they had planned on going. It had become a running joke that Bryan walked everywhere, and he planned to show Blair the path he had walked home that day along the lakefront and propose there with the Chicago skyline as a backdrop. However, Mother Nature had a different plan. Since there was a torrential downpour all day long plus a tornado warning for good measure, they decided to scrap Barcocina and instead went to Big Star, the actual first date location and a shorter walk away. After a couple hours of reminiscing on the past 3 years, they headed out because they had plans to go to a friend's birthday party, or so Blair thought. They walked towards the lakefront, but given the humidity and the threat of rain they returned home instead. Blair was attempting to freshen up before the party, but Bryan insisted on interrupting. Bryan dropped to a knee and proposed! Although Blair can't remember a word of what Bryan said, she said yes! But the surprise wasn't finished there... While trying to call family and friends to tell them the news, Bryan informed Blair that they "had to go" and an Uber was arriving in 5 minutes. Blair was very confused, but went along with it. A short drive later, they arrived at Barcocina - Blair assumed it was going to be her Chicago friends and family, but then spotted Mike, Bryan's younger brother, staring out the window at them. As it turns out, Bryan had planned a surprise party with Blair's immediate family, Chicago friends and his whole family, who had flown in from all across the country to be there! Best day ever!