Fiona hopes her moral compass isn’t leading her astray when she reconnects with Craig Heisner (guest star TAYLOR KINNEY), her married high school crush. But when she finds an abandoned purse with over five hundred dollars inside, she assumes her luck is finally changing. Meanwhile, Frank is willing to do just about anything to stay in Dottie’s good graces…even marry her. And in light of Harry’s demise, Debbie becomes obsessed with death. Kevin is thinking about buying The Alibi. Lip meets with a Colonel (guest star PETER MURNIK) to glean information for Ian about West Point. Jody asks Frank for Karen’s hand in marriage.