 After his marriage ends, Jack settles into a pattern of casual sexual relationships, including dating several women at once, each to fulfill a different need — including heiress Pizzarina Sbarro (Nina Arianda) — which he calls "Great Escaping".He also admits to Liz that he slept with Jenna "a lot" in Season 3.In the series finale, He reconnects with ex-girlfriends Nancy and Elisa, convincing them to embark in a group relationship despite both women's devout Catholicism and Elisa's imprisonment in a Puerto Rican prison.