Xavier Lamar, a 35 year old man, is "almost" ready to settle down with one woman and get married. Xavier has decided to step into the dating game one more time before he settles down. He decides to date a different woman each season of the year and from there he will decide which one he will commit to marrying. His best friend Derrick owner of the hottest café in town is there for moral support during his "Four Seasons" journey.