A Lot Like Love is about the twists and turns in the lives of two young people over the course of several years. The story begins with Emily Friehl and Oliver Martin meeting on a long flight. The two immediately hit it off and find that they are extremely attracted to one another. They cannot resist getting involved sexually while on the plane. As the two continue to talk during the flight, they both discuss what they would like to do with the rest of their lives. Oliver has his sights on creating a new website and is convinced that he will be a success. He is so sure of his future riches that he asks Emily to call him in a few years to see how he did.
When the plane lands, Emily and Oliver agree to go their separate ways and to just enjoy the brief fling that they had together.
However, three years later, Emily still has not found a man that enchants her as much as Oliver did that one day. As she is sitting home alone on New Year's Eve, she finds Oliver's phone number and decides to give him a call. The two then meet for dinner. The chemistry is still there, but both are reluctant to profess their love to each other.
As the years go by, the two occasionally meet for dinner to catch up and see where they are in life. Each time, the reunion finds the two stuck in relationships that do not seem as passionate as the one day they shared on the airplane.
Fortunately, they both find success in their careers, as Oliver starts an online diaper service and Emily is a successful photographer. However, romantically, the two can never get on the same page, no matter how many times they meet.
A Lot Like Love takes a close look at how strong relationships need time to be truly fulfilling. Though Emily and Oliver had a passionate one-day fling, they needed to gain maturity to realize what they truly needed in a partner.