Carolyn and Colton were setup by Carolyn's college roommate, Jill, and her brother Sam. Colton was working with Sam at the time. Colton reached out to Carolyn and not before long, Carolyn had agreed to a coffee date. Carolyn wasn't too sure how this whole thing was going to go at first, as Colton ordered a black coffee (which is apparently a 'red flag'). Although that didn't stop Carolyn from giving him a chance and soon they found themselves falling in love. After many friendly reminders from Carolyn, Colton finally got around to asking her to marry him.