Taylor & Alan
In early August of 2020, Alan & Taylor were both living in Chicago and trying to navigate their lives during the pandemic. To try to meet more people, both were on the dating app Hinge. When Alan saw Taylor's profile, he was intrigued by her interest in true crime. When Taylor saw Alan's profile, she wondered how it was possible that he had never lost a sock in the dryer. They began messaging on the app, and quickly transitioned into texting. Both felt that the conversation came easily, and they realized they had a lot in common.
On August 8, 2020, they met for their first date at Happy Camper in Chicago. They ordered pizza and cocktails, and were so deep in conversation that they didn't realize their 2 hour time limit on the table had expired until a waiter told them they needed to leave. Neither felt ready for the date to end. The date continued for 4 more hours, as they sat at an outdoor table at Old Town Pour House, sharing snacks and trying out craft beers. The two spent those hours eavesdropping on the dates occurring around them, and were thoroughly entertained. Eventually, it became dark and the two parted ways.
The following day, Alan & Taylor made plans to have lunch later in the week. Taylor was not yet working as a PA, and Alan had decided to use the 3 weeks of vacation time he had saved up to take a much needed break from working at SAE. What was intended to be an hour-long lunch date turned into an 8 hour lunch, dinner and drinks date, where they explored a variety of River North establishments. The conversation (and the drinks) flowed and the two realized how much they had in common and how much they enjoyed being around one another.
Alan & Taylor took advantage of the warm weather and the free time that they both had, and within a week or two, quickly realized that they had something special. Both deleted their dating apps and expressed that they no longer wanted to go on dates with other people. By the time the fall began, they were inseparable and made their relationship official. They have loved traveling together, meeting each other's friends, watching Formula 1, the Chiefs and UCLA gymnastics together ever since! Thanks Hinge!
Anyone who knows Sheryl Anderson, they know she is obsessed with a good family photo. Therefore, it was not unusual for Taylor to believe her mother when she told her they would be taking family photos over Christmas in Colorado. What she didn't know, however, was that it was just a ruse to capture Alan's proposal.
Alan had been discussing his plans to propose with Taylor's family since October, and used his time walking their dog Armie to discuss details with the Andersons, the photographer and the jeweler. Taylor was completely clueless. The day that Taylor flew to Colorado, her flight was delayed by 9 hours. Since she was bored, she logged into the couple's Furbo app to see what Armie was doing at home. To her surprise, she heard Alan on speakerphone with Sheryl and Sloane, discussing places to go in Aspen. Shocked by what she heard, knowing that they were probably discussing ideas for what Alan's parents would do in Colorado, she turned off the camera. She texted 3 of her friends, asking if they thought a proposal would be occurring. They assured her that it would not happen until after the New Year, and while the idea remained in the back of her head, Taylor moved on with the rest of the trip not really thinking about it.
On December 29, 2021, Taylor, Alan and the rest of the Andersons gathered in their backyard to take the family photos. Taylor thought there was maybe a 10% chance Alan would propose, and was completely taken aback when their "couple photos" resulted in an engagement. To add to the surprise, Alan's parents had driven to Colorado from Kansas City. The two families celebrated with champagne and a dinner at Casa Tua, where everyone got to enjoy the couple's favorite things: copious amounts of pasta and espresso martinis. The night concluded with hours of karaoke.
