Annie is 28, recently divorced, and just started volunteering at the JFK Library and Museum. While her goal was to make new friends, she wasn't expecting one of those friends to be Caroline Kennedy's son; Jack Schlossberg. Neither Annie nor Jack knows what they want in life, so as their friendship grows, so does their confusion. As things get more complicated, choices have to be made, and feelings have to be hurt. Will they get there, or will stubbornness and the fear of losing a solid friendship hold them back from what they want?