Jeff and Winter met the night of November 3rd, 2017 at Trinity Three Irish Pubs. Jeff was visiting some old friends that work there and Winter was just meeting up with friend for a couple of drinks. While at the bar, Jeff motioned for Winter to come speak to him. It took some convincing from Winter's friend, but she went to talk with him. The stars were aligned that night because Winter doesn't like to get attention while out with friends but, they hit it off! Jeff and Winter had their first date at Balzac two days later and started dating officially November 17th, 2017. They have been inseparable every since.
In celebration of Winter's birthday, Jeff got a reservation at Balzac, where they had their first date. The Packers were playing and the plan was to meet up with some friends at halftime. Jeff called ahead of time to talk to the manager and waitress about his plan, which was to happen as they were leaving at halftime. When they arrived at Balzac, they were seated at the bar, and the bartender was not aware of the plan. During dinner, Jeff said he had to use the bathroom and frantically found the manager so that he could adjust the plan. After finishing dinner, Winter went to grab her jacket and Jeff did the super original "I need to tie my shoes before we leave". When she turned around, Jeff was on one knee. Initially Winter said, "Are you f_____ kidding me!?" thinking that he was joking, but quickly realized what was happening and said "Bout time!"