Road Trip Romance

Buddy Love Meets A Road Movie. A pair of mismatched characters, often a world wise man and a high society woman (though the gender roles can be altered) find themselves in a situation were they must travel together to reach a goal. For the woman it will often mean returning home, while the man will often travel for the sake of some kind of reward for his troubles. They won’t like each other at first, there will be squabbles because of their class differences, but over time they find a common bond and slowly fall in love. The climax will often be after the couple has exchanged their First Kiss, Almost Kiss, or make love. The man will sneak off in the night to take care of Unfinished Business towards their mutual benefit, only for the woman to wake up alone. She feels betrayed, and finishes the journey on her own. The man will forgo his reward and make a dash after her for the sake of true love, maybe even defeat the Big Bad, and eventually they live Happily Ever After.

So pack your bags; first stop adventure, last stop romance, and we'll pick up some tropes along the way!

May or may not be necessitated by Chained Heat.

Anime

 * Spice and Wolf. An awkward traveling merchant and a haughty pagan wolf goddess teaming up to travel to her ancient homeland in the north fits quite nicely.

Fanfic

 * The iCarly fandom has this as a relatively common Fandom Specific Plot. Generally it involves the two people in the pairing going to visit the third. Occasionally it involves the pairing tagging along on a trip with the third member of the trio and whoever they are already involved in a relationship with.
 * iHit The Open Road is an example of a well written Creddie story of the first type.

Film

 * The Trope Maker is It Happened One Night. Peter as the hard bitten reporter, escorting high society dame Ellie back home for a big fat reward. In the end he leaves Ellie in the night to get money so they can marry. Ellie thinks Peter has left for good and goes back on her own. Peter forgoes the reward in favor of the trip’s simple expenses, and admits he loves Ellie, and the walls of Jericho fall.
 * Stardust: Tristan captures the Fallen Star Yvaine, to take back as a present for his beloved Victoria. After many adventures, the two make love. Tristian takes a lock of her hair to Victoria, as a way of fulfilling his promise to her, but admitting that he really loves Yvaine instead. Tristian goes back, fights the Big Bad, the two are reunited and marry.
 * Shrek: Shrek, an ugly ogre, risks life and limb to save Princess Fiona (more of an Action Girl than most other examples) so that he can get his swamp back from Lord Farquaad. After misinterpreting Fiona’s conversation with Donkey about “an ugly beast”, Shrek sneaks off in the night to bring Farquaad to her. Donkey clears up the misunderstanding and Shrek runs back to tell Fiona he loves her at the wedding.
 * The Princess and the Frog: Gender Role Reversal, Tiana is a low class working girl with the skills to know how to travel while Naveen is a spoiled prince. Over time they fall in love and Naveen is willing to forgo returning the human form and restoring his wealth in order to marry Tiana. However, he is captured by Faciler’s demons in the middle of the night, and Tiana thinks he has left her in favor of Charlotte. Ray corrects the misinformation, and she rushes to save him, and they live happily ever after.
 * Tangled: Flynn Rider is captured by Princess Rapunzel (though she doesn’t know she is a princess) and made take her to see the floating lanterns in return for the tiara he had stolen. The two slowly fall in love to the point of an Almost Kiss. Flynn sneaks off in the night to forgo his reward by returning the tiara to the Stabbington Brothers, who, along with Mother Gothel, turn him over the Royal Guard. Rapunzel thinks Flynn has left her and she returns home with Mother Gothel. Flynn, realizing the scheme, escapes from prison and rides off to save her. Once the Big Bad is defeated, they have the first kiss, and after years and years of asking, he finally said yes to her marriage proposal.
 * Anastasia: Dimitri plans to pass off Anya as a “fake” Anastasia in order to gain a substantial reward, not realizing until later that she is the real deal. Upon learning of Dimitri’s role as a con artist, she leaves him. However Dimitri refuses payment in the end, and once the Big Bad is dead (again) they elope.
 * The original Star Wars touches upon this. Han Solo is pretty much just Luke's ride. He agrees to help save Leia because of how he could rewarded, and leaves after he gets paid, but joins in on the fray to save Luke in the end. Han and Leia are at odds at first, but slowly fall in love over the course of "Empire".
 * A straighter example occurs in Spaceballs. Lone Starr saves Princess Vespa in order to get the Million Space Bucks reward, but forgoes it in the end. Eventually he learns that he is really a prince and races back to marry Vespa.
 * Corvette Summer, early 70s film staring Mark Hamill & Annie Potts. Both lower class: He's a just-graduated high school senior searching for a stolen Corvette, she's a self-proclaimed "prostitute in training."
 * The Sure Thing is a variation. The two romantic leads, Gib and Allison, are basically the same social class, but he is a would-be party animal and she is a compulsive planner. They are traveling together from the east coast to California, her to meet her fiance and him to hook up with a woman who is guaranteed to sleep with him. Much Belligerent Sexual Tension is generated between them on the way.
 * In Wristcutters: A Love Story the hero and his friend go on a roadtrip in the afterlife to find the ex-girlfriend he killed himself over, but pick up a new Love Interest for him along the way.
 * Chasing Liberty: She's the daughter of the US President, who's given her entourage the slip so she can have a holiday as a normal person. He's a free-spirited drifter she picks up along the way (but actually he's an undercover Secret Service bodyguard who set up a Meet Cute so she'd have somebody keeping an eye on her). Romance ensues.
 * Leap Year: Anna is trying to propose to her non-committal boyfriend in Ireland on leap year, as is supposedly "tradition". However, she lands on the wrong side of the Emerald Isle and has to take a road trip across the country with Declan, who annoys her to no end. You can pretty much guess how the story goes from there.
 * Romancing the Stone, a genre-savvy film (given that the character played by Kathleen Turner, the female romantic lead, is supposed to be a romance writer whose works frequently involve the sort of situation the writer finds herself in).
 * The African Queen
 * Cherry 2000. After the End, Sam's prize possession is a Robot Girl, the Cherry 2000. When the robot malfunctions, he has to hire a pretty female tracker, Edith "E", to go into the wastelands with him to find the necessary replacement parts. In the end he finds the robot's personality to be too artificial, he returns with Edith to rescue the Earth.
 * Rio. Blu is a domesticated, human-dependent, flight-challenged bird, while Jewel is an independent, free-spirited, highly-aerial bird. They are being matched to save their species, then being chained together, escape from an Evil Poacher. Then the adventures begin....
 * Pretty much the main point of the webcomic The Less Than Epic Adventures of TJ and Amal, in which a young man who's recently been disowned for, in the same move, refusing his Arranged Marriage and coming out to his parents needs to drive from California to Providence for his sister's graduation. Before departing he meets TJ, who's headed the same way and has lots of money but no driving skills. They're in bed by Reno.
 * Sex Drive has protagonist Ian and his longtime friend Felicia falling in love with one another as they drive to the home of "Ms. Tasty" with whom Ian is supposed to have sex.
 * Overnight Delivery has the hero, accompanied by a stripper named Ivy, driving crosscountry to retrieve a break-up video he sent to his girlfriend when he was under the impression she had cheated on him. Along the way, he and Ivy of course develop an interest in one another; by the end he discovers that and he ends up with Ivy.

Web Comic

 * The Less Than Epic Adventures of TJ and Amal falls directly into this plotline with the story following the two titular characters on the road from California to Providence, Rhode Island after Amal agrees to drive TJ while on a bender.