Trying to Win at Love tells the funny and inspiring story of a new tennis captain pressed into running a local team because "there's no one else." As his own expectations for success rise, the rookie captain begins to equate wins as validation from his players and competitors. His troubles, which aren't limited to the court, soon mount as quickly as his victories. He finds himself dealing with scheming opponents, bickering teammates, a commitment-crazed girlfriend, and a father he desperately wants approval from. A group of colorful characters and extraordinary events teach him valuable lessons about winning on the court and in life.