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TV host Will Chaney is as cute as they come, and he's a great dad to his young son Benjamin "Ben." The only good thing that came out of Will's marriage is the boy who is a little shy and confused. During a marriage breakup, Will has to pick up Ben from Denver airport and drop him off again at the end of every major school holiday. There, Will meets a divorcee named Jane, who also picks up and drops off her daughter, just like Will. Both good, part-time parents aren't going out with each other because they don't want their kids to go through another heartbreak. Luckily their best friends, Will's cameraman Charlie and Jane's sister Georgia, encourage them to go out together. When Ben gets used to the situation, he finally says "dad" instead of "Will." Then, he gives his critical blessing, even choosing Jane over the only other date his dad had for him. So Maddie can go. Finally, Will thinks about a risky move.