We first met on Match.com. We talked online for weeks about everything. For our first date, we met at Toadstool Bar in Highwood for a drink on March 11, 2017. Obviously, the awkwardness of meeting finally in person was there, but we both felt the butterflies. We walked to our cars and it started to snow lightly and then the kiss. That was it. We both knew. Fireworks was an understatement. We haven't been apart since.
We fell in love with Aspen years ago and have taken family vacations there to ski/snowboard every year. In March, we planned our first family vacation since the pandemic began. Jen had no idea that Gary was planning to propose there. He told all 4 kids that the plan was to ask Jen to marry him on the top of the mountain. Now, actually getting all 4 kids on top of the mountain at the same time was almost an impossibility for Gary. Days went by and Gary kept trying for the perfect moment. Finally, on one of the last days of the trip, the sun was starting to set at the end of a long, awesome ski day. We had picked Madi up from ski school and were heading up on the gondola to the top. Jen was tired and was not really interested in taking a picture at the top of the mountain, but even the kids insisted. Jen should have been suspicious of this as they usually are not excited to pose for pictures, but she was too focused on just getting it done. There was one couple at the top of the mountain who took our family photo. At this point, everyone started walking away and Jen thought they were done. Gary asked for one more picture with Jen. Gary was unsure if Jen would actually take the picture with him (this was when he was going to propose) so he quickly got down on one knee. Jen thought he fell and asked if he was okay. But, he proposed with a beautiful ring in front of all the kids. Jen looked up and the kids were crying and so happy. We looked out over the glorious mountains and skied down as a family and as an engaged couple.