The Last Kiss (2006)

Michael'd have a great job, still have his 4 best friends, and be in love with a beautiful girl at 30. He loves Jenna but his life seems predictable until he meets a college girl. It seems that everybody's having relationship problems. - Scott Filtenborg

Michael and Jenna, having been a couple for three years, want to get married and start a family. These plans seem to be well on their way when Jenna announces that she's pregnant. But Michael is worried that his life and his youth will be over for good. At a wedding of a friend, he meets a free-spirited college co-ed, Kim, who opens his eyes and leads him on a dangerous path away from Jenna. Meanwhile, none of the relationships of the people surrounding Michael and Jenna are happy and stable. Michael's friend Izzy is unwilling to let go of his childhood sweetheart Arianna; Kenny is a handsome stud who fears commitment to his latest conquest Danielle; and Chris is a co-worker who is dominated by his neurotic and overbearing wife over raising their newborn son. Even Jenna's parents, Stephen and Anna, are experiencing problems in their long-suffering marriage. - EdFlesch