Vinny was originally unsure just how far his friend Ansom should trust Jillian. While Vinny had some doubts about Jillian's loyalty, they seem to have respected each other professionally, and fought well in combat together. Their mutual grief over the reported croaking of Ansom brought them together at a deeper emotional level, and Vinny worked hard to make sure that Jillian and Don King had favorable first impressions of one another. When Faq was rebuilt, Vinny was assigned as a diplomatic liaison.
At some unknown point the two became lovers. Vinny tried to persuade Don King not to demand that Jillian pop a heir, in part because he feared it would ruin their relationship. While their relationship has become increasingly strained due to Don King's demands and Jillian's secrets regarding her alliance with Charlie, it has so far remained intact.
While Jillian left to join the Siege of Spacerock, Vinny found himself growing increasingly bored with his Duty as an ambassador. The only parts of his job that he liked were Jillian, and a nice message hat that came in as a close second. Finding Jillian's report from the Siege of Spacerock to be suspiciously brief, Vinny contacted Bunny, discovering to his shock that Spacerock had fallen, and that Jillian had ditched the battle to grab Ansom. Caesar's letter to prepare intelligence for an invasion of Faq will have only increased the amount of strain on Vinny's relationship with Jillian.
Vinny continued to care about his friend, despite being mean and a little bit crazy. But his loyalty remained to his side, and he dutifully carried out Caesar's orders. When Jillian returned home, she refused to speak to him, and he experienced a moment of jealousy when he briefly mistook Vanna for Jillian when Vanna and Duncan were having nookie.