Up in the Air has genre Romantic comedy. Romantic comedy has examples: Outside ProvidenceOutside Providence is written by Peter FarrellyPeter Farrelly wrote Outside Providence. Outside Providence has genre Teen film
[Human]: Can you recommend a movie like Up in the Air? [Assistant]: Up in the air may be related to these romantic comedies: Over Her Dead Body and Outside Providence. [Human]: O.k., That was a Farley Brother Comedy Right? I like that Genre, Can you recommend anything else? 
Yes, Peter Farley wrote Outside Providence. You may also like There's Something about Mary. That is another good comedy.