On a rainy Portland night, Jeff was out celebrating his 30th birthday with friends and family. Jeff happened to walk by a pretty redhead on the sidewalk waiting for her ride home. He made a snap decision, turned around and told his cousin, "I'm going to go and introduce myself". Ann wasn't sure about Jeff at first, but she appreciated his courage. As the conversation continued, Ann's UBER driver arrived and was waiting. She finally asked Jeff "Are you going to ask for my number or not, because I have to go" Jeff took her number and called her three days later.
It was a beautiful Fall day in November and Jeff had planned a day full of activities for Ann. They spent the day in the St. John's neighborhood enjoying brunch, window shopping, pizza, and Big Buck Hunter before heading to Cathedral Park (where Jeff planned to pop the question). While walking towards the waterfront, they heard the whistle of a train. Jeff started running and pulling Ann along to get across the tracks before it blocked his planned proposal destination. They made it, but unfortunately Ann's phone had fallen out of her pocket. Jeff knew what he had to do. He leaped up and over the moving train car to retrieve the her phone. Once he made it back over the train, Jeff was a little winded, but he was clearly on a mission. They continued towards the river's edge and when they arrived at his chosen location, Jeff pointed out a large sign that read "LOVE", then dropped down to one knee and proposed. The proposal was captured on camera by close friends who had been hiding. The happy couple then celebrated their engagement with a surprise party at Jeff's house.