Emily and Kevin

Engagement Proposal Ideas in Chicago

How We Met

Kevin and Emily’s story begins in high school. They were juniors at Rolling Meadows High School and it was almost prom season. Kevin had been nervous to talk to Emily so he figured “Hey, I’ll do the unheard of…ask a girl to prom who I had never talked to before!” And so Kevin asked Emily to prom and she said yes! Although they started out as friends, Emily and Kevin quickly started falling for eachother. They had a great time taking pictures and dancing together.

The next day, June 5th 2010, Emily and Kevin decided to make things official and start dating! They had a fun first summer of dating including a date in downtown Chicago.

As well as going to a Dave Matthews Band concert in Alpine Valley, Wisconsin. To this day, Emily and Kevin have gone to 12 DMB concerts together!

Their senior year of high school finished up and they attended their second round of prom together. This time, Emily and Kevin had been dating so there wasn’t any awkward asking to prom this time…

It was then time for high school graduation where Emily and Kevin were going to go off to different universities. Kevin attended the University of Illinois at Urbana-Champaign and Emily went to Mizzou. They were able to visit each other once every month or so…

…but being in love, the couple wanted to be together way more. Emily and Kevin decided to transfer together to East Carolina University in North Carolina where they became PIRATES!Emily and Kevin had an amazing senior year at ECU. Kevin signed an offer to join Fidelity Investments as a Software Engineer in Research Triangle Park, NC and Emily signed on to work at Cisco in Research Triangle Park, NC as a Health Fitness Specialist.

They graduated and enjoyed a celebration with their families downtown Raleigh, NC. It was now time for Emily and Kevin to begin the rest of their lives together.

Where to Propose in Chicago

Emily and Kevin's Engagement in Chicago

How He Asked

Emily and Kevin flew home to Chicago to spend time with their family and friends. Emily had a day planned in the city with her brothers on December 22nd, 2016. She went to the Art Museum and grabbed lunch downtown near Millenium Park. With the help of Emily’s brother Mac, Kevin was able to plan a surprise proposal. At the same location as their first city date, Kevin was standing at the top of the stairs. Kevin called her name after she reached the top of the stairs and she instantly knew what was happening. Kevin got down on one knee and proposed to the girl of his dreams followed by a quick YES! Emily heard cheering from afar and was surprised to see both of their families witnessing the proposal from Cindy’s Rooftop Bar.

After getting engaged, Kevin and Emily celebrated up at Cindy’s with their families and friends. Here are a couple pictures from the day!