Michael and Kiley Matched on Bumble and agreed to meet at Indulge Wine Bar for dinner and drinks.

Kiley picked a poor time to decide she "knew her way around Denver" and no longer needed Google Maps as she went to the wrong Indulge wine bar. She proceeded to wait 15 minutes and then let Michael know how displeased she was that he stood her up. He then informed her she was at the wrong location. From there Kiley proceeded to the Centennial Indulge wine bar and finally made it 30-40 minutes late. Kiley felt so bad about the whole thing and assumed the date couldn't be salvaged. She chose not to order any food assuming this guy would never ask her out again. By the time she got there it was last call for the kitchen and Michael ended up being the only one to order food which he felt awkard about. The conversation was good but soon after the date began it was last call for drinks. Michael tried to salvage the date by taking Kiley out afterwards to walk around and see the Christmas lights. Kiley tried her best to follow through with his plans but she couldn't take the cold. Michael walked her to her car and got her number. She proceeded to call her sister and tell her about how unlikely it was that this guy would ever call her after her tardiness. Luckily Michael's persistent and he called her for another date despite her poor first date etiquette.

After a solid second date at the Aspen Grove Christmas Market and brunch at Bacon House Social Michael decided to throw caution to the wind in Kiley's opinion by inviting her on a 10 mile hike for the third date. She went back and forth on whether or not it was a good idea to drive up in the woods an hour and a half and take on a 10 mile sort of day of hiking with someone she'd just met. She texted her friend Amber in the early hours of the morning lamenting adding "outdoorsy" to her dating profile as she was about to embark on one of the longest hikes of her life at this point in the middle of winter when she hates the cold. She worried she'd bit off more than she could chew with this wondering if second date conversation could really last that long. What might happen if it went sour on mile two or three. Michael apparently thought this wasn't that strange of a request and was not concerned. Luckily the date went wonderfully and the conversation flowed. To Kiley's suprise Michael ended up asking Kiley to go out for dinner and drinks on the way home. Kiley was shocked she didn't scare him away with the constant stream of conversation and thought wow, this could go somewhere. The whole date lasted probably 10-12 hours and was the start of something wonderful.

Thanks to a bomb cyclone snowstorm Kiley stuck around Denver for a fancy date planned by Michael. The two went to an Immersive Monet exhibit and Kiley made pineappe boats early on. Michael intiated their first photo together at the museum.

The pair continued to text back and forth over Christmas Break after Kiley went home to Nebraska for the holidays. Michael noted that he would spend lots of time analyzing and crafting the perfect thoughtful text and then Kiley would fire one right back moments later. Kiley thought things are going well, I should bring him something back from Nebraska. She wanted just the right level of commitment for the first few dates so Kiley picked up a bag of popcorn for him from her hometown popcorn store. She had planned to pick him up a 6 pack of her favorite Nebraska beer. Her family caught wind of this and said to her, "That's the bag you bought....Well I think we know what you think of him... You didn't even get the big bag..." Kiley was so embarrassed she talked her sister and brother-in-law into going back to pick up more bags. She did really like him but she didn't want to be too over the top with a Christmas present a month or so in... That being said, the popcorn joke lives on...

Michael invited Kiley to join him on a ski trip with his friends in Vail. Michael's friends proceeded to ask him if Kiley was his girlfriend or a friend. Michael responded, let's just go with Kiley. The two had a great time in Vail. It led Kiley to initiate the conversation as to whether or not he was considered her boyfriend.

Kiley planned a memorable surprise date for Michael's birthday. She had him open clues that led him to the Olympic Training Museum and Training Center where the two discovered their mutual love for the Olympics. The two finished the night eating at the Airplane Restaurant eating in a WWII plane.

Kiley invited Michael on their first out of state trip to attend a murder mystery party in San Francisco. Kiley's friend Emily hosted a huge murder mystery party for her birthday and the pair were cast as the maid and butler. Kiley was killed early on unexpectedly and Michael did some improv to show some emotion for his late wife off script. It really misled people with the final solution. Afterwards the two spent a few days with Michael's brother Chris and his family while exploring the city.

Kiley presented Michael with an idea that they should go on a date that is associated with each letter of the alphabet starting at her summer break. In the book she typed up a letter and signed it "Love, Kiley." Michael responded with, "I see what you did there. Is that how you feel....because that's how I feel..." With that being said it's hard to say who said I love you first. The two really enjoyed doing a date, trip or activity for each letter of the alphabet. Kiley turned it into a book that you will see at the wedding.

Michael and Kiley enjoyed spending the summer and fall of 2023 enjoying Colorado adventures.

The pair took their first big adventure abroad when they spent twelve days touring the mainland and islands of Greece. They found that they really enjoyed the bus tour adventure and finished the trip with island hopping in Santorini and Mykonos. The two loved getting to enjoy a trip that felt like they were living in the historical documentaries they both love. Michael particularly enjoyed seeing many of the places he'd envisioned from his video game that inspired the trip. Michael said the trip was partially a test to see if this relationship would make it through the long haul. At the end he decided they passed and started ring shopping shortly after.

Michael got the chance to pass Kiley's test this time when he went on his first cruise. Kiley's a huge cruise ship enthusiast so she was happy to hear that Michael thought the trip was, "Fabulous." He noted that it was so nice to have a trip that schedules 20-30 dates in a week for you with very little effort. They enjoyed visiting The Dominican Republic, St. Thomas and Tortola on the trip.

Michael took Kiley out to dinner and then out to Daniel's Park to paint the sunset. She had been talking about painting the sunset for a while as she always tries to fit time in for those during their travels. Michael proposed to Kiley and arranged for both of their familes to join them as surprise. Originally Michael had planned to do this before Kiley's trip back home to Nebraska. Plans were changed however as Michael broke his nose playing basketball in the weeks prior to the proposal. Michael asked the surgeon how long he could wait to do the surgery without rebreaking his nose and was able to delay the surgery five days. He decided to move his proposal plans up to Memorial Day weekend and miraculously Kiley's family were able to come up from Nebraska in time. Afterwards, Michael planned an engagement party at the Lazy Dog Brewery in Highlands Ranch.