Back when Emily and Zack were young, naive juniors in high school, Zack's friend Ross (one of Zack's groomsmen) brought Zack along when he was hanging out with Emily and her friends. While nothing came of that initial meeting (although Zack will tell everyone Emily wrote Happy Birthday once on his facebook wall), fast forward to the end of their senior year of high school, and Ross once again brought Zack to hang out with Emily and her friends (thanks Ross!). After this time, Zack asked one of Emily's friends for her number and the rest is history!

In September 2018 after 8 years together, Zack and Emily decided that they would go look at rings together on a Friday after work. Little did Emily know, Zack had already purchased the ring beforehand and was planning to surprise her with a proposal that day. Zack was out of town for work and was supposed to come back on Thursday evening to prepare for that Friday, but he ended up getting laid over. At the last minute, Emily had decided to call in sick from work on Friday, which made things even more complicated for Zack.

After Zack landed at the airport that morning, he met Emily's parents to celebrate the upcoming proposal. Emily was waiting impatiently for Zack to come back so that they could go look at rings together. Zack had his friend Jared (groomsman) ready to meet the two on the Chicago Riverwalk around 5:30pm that day as both Jared and Emily were supposed to be at work. Since Emily was home already, she figured that they could go early. Knowing he had to wait for Jared, Zack started dragging his feet that afternoon to kill time. They finally went down to Jeweler's Row, but Zack didn't have any store in mind much to Emily's dismay - he already had the ring so he didn't do any research on where to go!

After browsing through a few stores, Zack and Emily walked back towards the Riverwalk. Luckily for Zack, Emily had confirmed what she wanted for a ring, which was exactly what he had in his pocket - bullet dodged! They got to the Riverwalk right on time, and Zack started looking for Jared. But Jared, unbeknownst to Zack, had gone incognito – grew a beard and was wearing a hat and sunglasses – so Zack didn't recognize him right away. Emily thought Zack was acting weird and started dragging him up the stairs to the street level. Finally, Zack finally spotted Jared with his camera and got down on one knee. Emily was so surprised, and she said 'YES!' and the rest is history.