Cherrieann and Rocco didn't meet in college or at work, they met on an online dating app. Cherrieann's friends suggested that she make a Tinder Profile. She was very optimistic about possibly finding someone to have a life-long relationship with. One of the benefits of online dating for her was that she could weed out the men who weren't looking for a long term relationship and didn't share the same values as her. After a month and two failed dates, she was scrolling through her "likes" on Tinder and saw a handsome guy named Rocco, she swiped right and they started messaging back and forth. Their conversation started out very flirty as they were getting to know each other. Rocco knew that Cherrieann was the girl he wanted and he was relentless in asking her to spend time with him. Even though Cherrieann was interested in Rocco she had trust issues that made her hesitant to go out on a date with him. Finally, Cherrieann said yes to going on a date with Rocco. Their first date was on October 13th, 2018. The plan was to go to the Hispanic Heritage Street Festival & Health Fair in Chinatown, Honolulu. Once they got to the festival, they weren't able to find any parking so they decided to go eat . As they waited for a table at Cheesecake Factory they sat in the park and chatted for over an hour.

Fast forward 2 years, Cherrieann was grocery shopping and Rocco called her to tell her that he just picked up her anniversary gift. He told her to leave her cart and come home because he wanted to give her the anniversary gift. She left her cart in the middle of the aisle and rushed home. Once she got home, she called Rocco to let him know that she arrived. He told her "follow what you see", when she opened the front door she saw rose petals leading from the door to their bedroom. When she entered, Rocco told her to turn around and close her eyes. A few moments later, Cherrieann turned back around and Rocco was on one knee and said "Cherrieann, will you marry me?"