Tommy and Vanessa first met when Tommy was in college, and friends with Vanessa's older sister Jacqueline. When she first met him, she couldn't help but ask her sister who he was... and she definitely had a little crush on him. Her sister told her that was her friend Tommy, and said “absolutely not!” Vanessa never thought she would see him after that, but fast forward 6 years later when they crossed paths at the Willowbrook mall. They caught up for a little bit but eventually went their separate ways. It was only a matter of time before Tommy asked Vanessa to catch up one day over a drink. Fast forward, now they have a townhouse in Randolph and a golden retriever named Willow (after the Willowbrook mall).