 This episode was actor Dean Winters ' third appearance on the series as the character , Dennis Duffy , a former boyfriend of Tina Fey 's character , Liz Lemon . He appeared in the episodes " Jack Meets Dennis " and " Tracy Does Conan " . Finkel has appeared on the show in a 10 @-@ second internet sitcom , Makin ' It Happen , alongside staff writer Kay Cannon . The two play husband and wife . A series of Makin ' It Happen was produced and the webisodes aired on NBC.com. 
