Air Voyance

"Daniel is traveling tonight on a plane I can see the red tail lights heading for Spain Oh and, I can see Daniel waving goodbye God it looks like Daniel Must be the clouds in my eyes"

- Elton John, "Daniel"

Characters standing outside an airport always know exactly which plane has their beloved on it, even if they lost a Race For Your Love. Planes take off from airports every few minutes, but characters psychically know which one is theirs.

If there's a POV shot from the ground, you'll see the face through the window, rather than a more accurate view that looks approximately like a small dot in the sky. (Fridge Logic dictates that even if the plane were close enough to see in the window, you'd have to be right under it.)

Bonus points if they wave to each other through the window or something. See also Airplane of Love. Could be justified if it's a very small airport, but not likely if it's any kind of large passenger plane.

Anime and Manga
"Endou (gazing at the contrails in the sunset): Do you think that's his plane? Otonashi: Yes, probably. Endou: Let's play together again sometime!   (right behind them): Yeah, let's!"
 * In Honey and Clover, Takemoto pulls off a completely platonic Race For Your Love toward Morita, but gets there too late. He ends up behind a chain link fence outside the airfield. No idea how he knows which plane it was, but he hurls some choice epithets at it as it goes by.
 * Subverted in Inazuma Eleven:

Comic Books

 * Amazing Spider-Man #93: Peter Parker wants to head straight to Gwen Stacy and confess his Secret Identity before she leaves (due to the death of her dad, which was somwehat caused by Spidey.) Unfortunately, a fight delays him and he rushes to the info desk. The receptionist tells him the plane is departing. Peter turns and looks out the window - sure enough, the plane's just left.

Film

 * Used in Apollo 13: When Tom Hanks' character (Jim Lovell) takes off for Florida, his wife watches from the yard as his plane flies over the house. May be justified in that it was a military plane and therefore quite unique-looking, or Hand Waved in that seeing any old random plane made her think of him (as astronauts are pilots first).
 * Taken Up to Eleven in a later scene, where Jim Lovell looks down at the Earth through a window in the lunar module, and his wife stares back up at him from her living room.
 * Subverted in Bitter Moon, when the evil monster of an Anti-Hero places his girl in a plane, but I can't remember his reaction.
 * Played with: In Final Destination, the group of characters who just got kicked off the plane are able to track the ill-fated flight as it takes off, but get distracted with another argument as we continue tracking the plane. They start paying attention again when the shockwave from the otherwise silent explosion takes out the picture window. Justified here because they were right outside the gangway (or whatever that thing is called).

Music
"Pedro Comacho, The former informer of the secret police is still standing outside the club. Pretending to be blind, he watches the last plane to Miami dsappearing in a flaming purple sky. Now he knows he has been left behind."
 * As quoted above, Elton John's "Daniel" is all about this.
 * There's a song from Yello that uses a non-romantic example. It's called La Habanera. It's on "One Second," the same album that made the "Oh Yeah" song famous.

Newspaper Comics

 * Aptly harpooned in the Filipino comedy comic Beerkada, where, after seemingly losing a Race For Your Love, the main character Glenn hangs outside the airport screaming lovelorn confessions at every plane that passes for the rest of the entire night. Later on, it turns out the girl he was looking for wasn't even leaving for another month. He mourns her loss anyway.

Visual Novel

 * This official art of Ace Attorney.

Western Animation

 * In a non-romantic example, the Spider-Friends are hanging out at the airport watching the plane that has Kraven the Hunter being sent back to his home country.