It all started with an app notification from Hinge. Gretchen's profile mentioned that she had won Harry Potter trivia....twice, and James was hooked!

James almost blew it off the bat :( Luckily, Gretchen was extremely understanding!

James was at least smart enough to immediately get their first date rescheduled!

Gretchen and James had their first date on the patio of AJ Hudson's. Gretchen didn't need to execute the escape plan she had hatched with some of her friends, and plans to grab a drink turned into a full dinner together.

Gretchen met Echo on their second date, which included a walk around Humboldt Park. James knew he had a winner when 1) Echo was instantly in love and 2) Gretchen brought chocolate chip cookies to share.

After 5 months of dating, Gretchen and James took their first international trip together to Mexico. This has since turned into an annual trip.

James ingrained the importance of tailgating in Gretchen when they attended their first ND football game together.

Gretchen and James celebrated their first NYE AND family wedding together - Gretchen's brother Andy and sister-in-law Colette!

Gretchen moved into James's condo, and Echo couldn't have been happier!

James worked up the nerve to pop the question at dinner at Maple and Ash. Gretchen thought she was taking James out to dinner for his birthday, which allowed him to completely surprise her. The waiter brought out a custom menu for "dessert" after dinner to help drive the important question home. She was so caught off guard, that she only said 'No' 5 times before saying 'YES!'.

James and Gretchen traveled throughout Scotland and Ireland, checking off two places on Gretchen's bucket list.

The couple moved into their new home together and celebrated with a "cheers" to their future.