The Third Wheel

After more than a year of fantasizing about Diana, Stanley finally asks her out on a date. Their coworkers form an office wagering pool and start monitoring the prospects of the date with keen interest. The setup foreshadows the chaotic night to come.

The coworkers continue to watch as the date unfolds, betting on how far Stanley will get with Diana. The implicit surveillance adds pressure and humor to the evening. The tension between romance and prankish curiosity becomes a running thread.

Stanley and Diana leave the party for drinks and head toward the theater. On the way, Stanley accidentally hits a homeless man, Phil, with his car. They pause to assess the damage and figure out what to do next.

Stanley offers to pay for Phil's injuries and broken belongings. They withdraw cash from an ATM and take Phil to the hospital, hoping to avoid further trouble. Phil's limp and presence complicate the date but pull Stanley deeper into the trouble.

Despite the chaos, they reach an open-air performance just in time for the second act. The event is a random series of monologues by famous figures, providing surreal humor. Phil reappears wandering the stage and delivers a monologue on bread, earning a standing ovation.

Stanley discovers his car was parked in a tow-away zone. Diana and Phil accompany him to the impound and, on the public bus ride, Phil nudges them to interact with strangers and sing together. The night blends inconvenience with performance.

They reach the impound and find the attendant uncooperative. Diana flirts with him to smooth the process, and they end up paying nearly 150 dollars to reclaim the car. The episode strains Stanley and Diana’s budding romance.

Stanley changes plans and invites Phil to eat with them at a Japanese restaurant. Diana almost shares a kiss with Stanley, but her ex shows up, complicating the moment. Phil's presence keeps the situation quirky and tense.

When the ex causes trouble, Phil defuses him with a slap and then soothes the atmosphere by singing Puff the Magic Dragon. His antics steal the spotlight and steer the night back toward lighthearted chaos. The restaurant scene showcases Phil's unpredictable charm.

After dropping Phil off, Stanley tries to find a place for him to sleep, but it seems Diana is shutting him out. He hesitates, then starts reconsidering, indicating a complicated bond with Phil and Diana. The charity of the night is overshadowed by practical concerns.

Stanley turns back to keep Phil from harming Diana and seizes a chance to kiss her. The moment marks a turning point, merging the chaotic night with a real romance. It closes the date on an unexpectedly intimate note.

In the final scene, Phil seems okay, revealing himself as more of a con artist than a shelter-seeker. He exaggerates his persona and ends with a stunt by throwing himself in front of a tow truck, echoing his earlier trick. The wrap-up hints at a lasting, sly trickster who lingers after the date.