Love is in the air, or so Frasier thinks. Determined to "give Cupid a win" on Valentine's Day, Frasier inadvertently becomes involved with both sides of a troubled relationship.
Roz takes Eve and Olivia out for a much-needed night on the town, leaving Frasier, Alan and Freddy to take care of Eve's baby. While the ladies bond, the men argue over which one of them will stay home with John for the evening.
On the anniversary of Adam's death, Frasier learns that Freddy is seeing a grief counselor and tracks her down in order to find out what's wrong. However, he makes a rash decision in her office that leads to a crisis.
Frasier's agent Bebe Glazer visits, leading Frasier to wonder how he can have more in common with her opera-loving daughter than with his own son. Along the way, he suspects there's more to the story than Bebe first lets on.
When Frasier sees that Eve is ready to date again, he enlists Roz's help to plan a romantic weekend for her and Freddy at a beach house in Cape Cod. But Freddy and Eve suspect something else and take actions of their own.
When Frasier hears that a famous reclusive author might be at his tailgate party, he enlists Alan and David's help in locating him. Meanwhile, after a mix-up, Olivia deals with two fake boyfriends in an attempt to impress her sister.
When Frasier, Freddy and Roz go back to Seattle for a KACL anniversary special, Frasier reconnects with a former caller whose life went off the rails after he took Frasier's advice. Alan's lack of appreciation drives David to quit.
When Olivia decides to host a surprise murder mystery party on the night of Frasier's second date with Holly, he tries everything he can to get them out as quickly as possible. However, a real-life disaster changes everything.