Erin and Jason met on an online dating app, Bumble, where Erin initiated the first conversation. She charmed Jason with a witty comment about making a mean grilled peanut butter & jelly sandwich, while Jason impressed her by mentioning that he had gone to a Lenten fish fry the night before with his friends. "A good Catholic boy?! My mother is going to love him!" was Erin's immediate reaction. After finding out Erin ran the Chicago marathon just as many times as he had, Jason foolishly bragged about his ability to karaoke to a few 90s rap songs - which Erin made him prove a few dates later.

Erin and Jason's first date was about a week after connecting on Bumble. They met for a drink at the Blind Barber in the West Loop, had dinner at Fulton Market Kitchen, and ended with a nightcap at Boss Bar in River North. No more than two drinks into the night, Jason, with Erin in hand, made his way to the bar. After ordering drinks, Jason planted his first smooch, and soon after, Erin's legs began to give out. Apparently Erin had done a double workout that day and was very dehydrated. She started to faint from fatigue and Jason wrapped his arms around her. Erin stood back up but then fainted again, and by then people thought Jason was bear-hugging a random girl that may not be of sound consciousness. Sensing scowls with people thinking the worst, Jason begged Erin to come sit at the bar and drink some water before he got beat up. To this day, Jason still thinks it was the kiss.

After work on the evening of January 24th, Erin and Jason headed to Lincoln Park for a dinner date at North Pond restaurant. The feel-like temperature was -20 outside - nice planning, Jason. After getting out of the Uber, they made their way into the romantically lit & snow covered park and toward the restaurant decorated with twinkle lights (Erin's favorite). They held hands tightly as they moved carefully across the icy sidewalks. Under a lamp post, and about 20 yards away from the restaurant, Jason turned to face Erin and got down on one knee to propose. She said yes, and his knee thawed out about the time they ordered dessert.