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While working for an escort service in Detroit, Michigan, Jarod "Gere" takes an assignment as a special consultant to Cynthia Sloan, a socialite and real estate development tycoon. She believes that he's there to save her the inconvenience of men "hitting on her" when she's at social gatherings. In reality, Jarod took the position in order to uncover the truth about the death of an 8-year-old boy who supposedly fell from the rooftop fire escape of the Jefferson Heights apartment building.

The only way to have enough room to develop the new "Sloan Towers" for the downtown area was to have the Jefferson Heights apartment building condemned. Sloan's manager, Frank Linden, used sulfuric chloride to weaken the bricks around the fire escape that led down from the roof, in order to cause an accident so terrible that the city would have no choice but to condemn the building.

Jarod lures Frank to the roof of Jefferson Heights by sending him a note from Cynthia, written on a chocolate heart, inviting him to celebrate his promotion with her. After Linden climbs onto the fire escape, where the table is set for a romantic dinner, he opens what he thinks is a bottle of champagne and pours it into the glasses on the table. The bottle contains sulfuric chloride and the glasses are plastic. They quickly melt, the acid weakens the bricks to which the fire escape is attached, and Frank Linden finds himself hanging on to the ledge by his fingertips, to keep from suffering the same fate as the 8-year-old boy. To convince Jarod to grab his hand and save him, Linden confesses.

Frank gets arrested and Cynthia Sloan decides to renovate the building, rather than tear it down, keeping hundreds of people from being evicted.

Jarod "Heart" writes a book entitled The Saddest Little Valentine and leaves it for Miss Parker to find in an adult bookstore. A scantily clad Miss Parker is on the cover, and the book is a thinly disguised tale of the lonely life she's led since her mother died.

Jarod patches up the 25-year marriage of Joyce and Howard - sending them to Paris for a second honeymoon and discovers Valentine's Day, chocolates and hearts. He sends Miss Parker a Valentine's gift - an invitation to be his Valentine.