Robby and Jess knew each other in high school but did not begin hanging out until mutual friends brought them together in 2016. They met up to see each other as friends a few times but both realized very quickly that what they had was something special. One night, Robby asked Jess on what was going to be the "will you be my girlfriend" date - they made it to the end of the date, Robby's nerves ran a little too high, and Jess was dropped off... not a girlfriend. Knowing that she didn't want to wait for another date to be asked, she promptly texted Robby and informed him that it was official, they were dating.

Robby and Jess were pretty positive early in their relationship that they would get married in the future. One day, Robby made a silly comment about how if they were still strong and in love when they reached three years of dating, he would propose. The third year of the relationship came and Jess dropped several, very subtle, hints that it was time for Robby to pop the question. The holiday season rolled around and one night, Robby took Jess to look at Christmas lights. He took her to a spot that they had been to several times before and began his wonderful speech. Jess knew this was the real deal because, in his speech, Robby admitted for the first time ever, that Jess is a hilarious person. She was so overcome with excitement and nerves that she said "yes" before the question was even asked.

Robby and Jess are looking forward to their future together as newlyweds! Jess is tantalizingly close to graduating and starting her career as a teacher while Robby is consistently growing in his career field at the dealership. The two are looking forward to a honeymoon in the (hopefully not too distant) future and a lifetime of love (and dogs).