~Todd was so sweet and wanted everything to be perfect for the big proposal like every guy out there. Unbeknownst to Jen, he had spoken to her Dad about marrying her in October while at a brewery tour (and after a few brewskis ;-) Todd took his mother ring shopping as a sweet gesture, and ultimately picked the diamond but designed the setting himself. He spent Christmas Eve with Jen's family, and was going to propose then. Problem was, Jen was fighting a horrible virus and had barely any voice at all. He probably wanted to actually hear Jen say "yes", so he opted to wait until another time ;-)
On New Year's Eve, they were on their way out the door to a friend's NYE party. Todd asked Jen to run upstairs quick so he could give her something. Not thinking anything of it, she proceeded to tell him they should probably go to the party. He complied, and so yet again another lost opportunity to propose! Oops!
Finally, the weekend of January 8th, they spent time at a family birthday party. On that night while alone he asked Jen to go to the rooftop where there was a beautiful view of the skyline of Chicago. He told her that he had something to give her, but being that it was after Christmas and the holidays, again she didn't think much of it. Since they were going outside, she thought it might be a bike or snowshoes, since he told her the gift had been outside for a few weeks (total lie.) She was thinking...she could use a new bike! Then he had her close her eyes. He was starting to tell this story about how he had this woman stitch this piece of clothing for Jen, and it took her a while to make it since she is 5'10". It was bizarre, and he was acting really nervous! Then he proceeded to say some nice things, which of course she doesn't remember since she was starting to figure out what was going on! He then said "Marry Me, Jenny" (which he calls her sometimes) and got up right away. Since Jen wanted to remember him on his knee, she asked if he would get back down so she could say YES! The ring sparkled even in the dark of night! They were so excited. They then took a walk by Lake Michigan and no one was out, so it felt like they had the city to themselves. They sipped champagne in their thermos's, and took some pictures.