Wrong Guy First

This is the plot that results when a Love Triangle is used to illustrate the Aesop "Be Careful Who You Give Your Heart To"

Our heroine is a young woman with two suitors. Suitor #1 is rich and handsome. He is charming, witty and charismatic. He seems to be everything a young woman would want. But he isn't.

Suitor #2 appears to be flawed. If he's rich, he's not as rich as Suitor #1. If he's handsome, he's not as handsome. He could be many years older than our heroine. He often has the kind of personality that makes him hard to get to know.

So naturally, our heroine picks Suitor #1. And she's happy, for a while. But then things go horribly wrong.

Maybe Suitor #1 leave town for a while, and returns with a fiancee. Maybe his parents persuade him that our heroine isn't good enough for him. Maybe our heroine has money problems, or family problems, or health problems, and Suitor #1 uses them as an excuse to break things off. By his actions, he has shown himself to be the wrong guy.

Just when our heroine despairs of any help, who arrives in her hour of need? Suitor #2! He doesn't expect our heroine to fall in love with him, but he helps her anyway. He just wants his beloved to be happy.

This story often has a happy ending. All that's needed is for the heroine to recognize that Suitor #2 is the right guy, and fall in love with him. He never cares that he's her second choice.

Why does the young woman choose the wrong guy first? Because if she picked the right guy first, there wouldn't be a plot.

In many cases, Suitor #1 may be the local bad boy, because... well, you know. If a character can never choose between two suitors, then this is a case of Betty and Veronica instead. Compare First Girl Wins. This same general plot can work with the genders inversed, so that it's the Wrong Girl First.

This trope is often used by fanfic writers in a Die for Our Ship scenario, where Suitor #1 is portrayed as abusive and cruel (regardless of him/her really being like that or not) in order to justify having the young woman/young man run into the arms of Suitor #2.

Anime & Manga

 * Three events in Peach Girl are within lumping range of this trope, but in the first two, the demonstration of wrongness is false, and the third.
 * Inverted by Haruna of High School Debut. She initially falls for Fumi, a perfect example of Suitor #2, but instead ends up with Yoh, textbook example of Suitor #1.
 * In The Tower of Druaga, Fatina falls for The Stoic bad boy Neeba in The Aegis of Uruk, but after, develops feelings for Neeba's younger half-brother Jil. But this trope is subverted in the end in that Jil never gets over Kaaya and the two eventually make up, leaving Fatina as a romantic loose end once more.
 * In Rose of Versailles Oscar pines for Fersen for years...before she realizes she truly loves Andre.

Comics

 * In Spider Man Loves Mary Jane, M.J initially nurses a crush on the daring Superhero Spider-Man, but after an awkward date with him eventually comes to the realization that she's actually in love with her geeky algebra tutor Peter Parker. Anyone who is familiar with the Spider Man mythos will tell you the irony inherent in this little set-up.
 * M.J also goes through something similar with charming-but-manipulative Harry Osborn, although mainly because Peter has started dating Gwen Stacy instead (hint: the romantic entanglements the teenagers in this 'Verse go through are complex indeed), but eventually breaks it off with him. In something of a reverse, Harry actually is in love with her, but M.J isn't in love with him and feels it would be unfair to string him along.

Film

 * Happens a lot in chick-flicky Romantic Comedies. Examples include:
 * Sweet Home Alabama, where the main character almost ends up marrying her initial suitor, only to fall back in love with her old flame.
 * Bridget Jones's Diary; Bridget initially pursues her boss, professional cad Daniel Cleaver (against her better judgement), and resists pursuing right man Mark Darcy as she believes he had an affair with Daniel's fiancee.
 * Major part of the plot of Jab We Met. The two main characters meet on a train and through a series of misadventures end up going on a road trip throughout India together. Although Aditya falls in love with her fairly quickly, Geet... already has a boyfriend.

Literature

 * Jane Austen loves this trope:
 * Persuasion may be unique among stories for having a Wrong Guy First scenario where Suitor #1 and Suitor #2 are the same person, with eight years' growing-up in between.
 * In Sense and Sensibility, Mr. Willoughby dumps Marianne Dashwood for a rich woman. Marianne eventually marries Colonel Brandon. Elinor, for her part, is in many ways the right woman in Edward Ferrars' Wrong Woman First scenario; the two fall in love, but are prevented from acting on their feelings by Edward's rash earlier engagement to the opportunistic Miss Steele.
 * Elizabeth Bennett of Pride and Prejudice is initially charmed by the smooth-talking Wickham, before Mr. Darcy exposes Wickham's true nature and wins Lizzy's heart. In a slight variation from form, Mr. Darcy is a much better catch than Wickham in every way: he is far wealthier, well-connected, young, handsome, kind -- pretty much perfect, as many a fangirl will tell you -- he just lacks Wickham's natural charisma and comes off as stoic and unfriendly -- which, due to Values Dissonance, only earns him more points with modern fangirls. As Lizzy herself puts it, "One has all the goodness, and the other all the appearance of it!"
 * Emma and Frank.
 * In The Small House at Allington by Anthony Trollope, Lily Dale picks Adolphus Crosbie over John Eames. Adolphus breaks their engagement to marry Lady Alexandrina de Courcy.
 * In The Prime Minister, also by Trollope, Emily Wharton marries Ferdinand Lopez, who only wants her for her money. After his death, she marries the man who truly loves her, Arthur Fletcher.
 * In Can You Forgive Her?, two women go through this. Glencora loves the abominable Burgo, but ends up marrying the solid Plantagenet. Alice initially loves her cousin George, but after he goes through a wild period breaks it off and becomes engaged to bland but respectful John Gray. Mrs. Greenow doesn't really fit this trope.
 * Far From the Madding Crowd by Thomas Hardy also has this, although it gets even more complicated with the addition of Suitor #3, who's not quite as graceful towards Suitor #1 as Suitor #2 is.
 * Reba McEntire's One Promise Too Late has a milder version, where the guy the heroine married isn't so much wrong or bad as less fulfilling than the one the singer meets later. To the woman's credit, she says, basically, "I can see you're my soul mate and I'd be happier with you - but my husband's been good to me all these years, and I won't betray him now." So, Downer Ending with character.
 * Done twice in The Gardella Vampire Chronicles. Victoria has three love interests within the books. She marries Phillip, who gets vamped and she has to stake him. Later she has a fuckbuddy-type relationship with Sebastian, but is obviously going to end up with Max.
 * The plot of New Moon is this to letter - perfect prince Edward leaves Bella and sincere I-Want-My-Beloved-To-Be-Happy poster guy (for this book at least) Jacob happily sweeps up the ashes and befriends her. Subverted in that Wrong Guy First comes back in the end...
 * In Harry Potter, Harry, Ron, Hermione and Ginny all date at least one person before getting together with their future husband/wife. At the age of seventeen/eighteen.
 * In Great Expectations, Estella marries the abusive Bentley Drummle, Pip's rival, to spite Miss Havisham. He is later killed in a horse riding accident, and in the Revised Ending (in the original ending she remarries with a different man), she reunites with Pip in a Maybe Ever After scene.
 * Nicole Baart's trilogy beginning with After The Leaves Fall plays around with this a lot. In "After The Leaves Fall", is the wrong guy for Julia and  would seem to be the right guy.... In "Summer Snow", ...and in the final book, "Beneath The Night Tree",.
 * In The Hunger Games, . Subverted somewhat in that.
 * In PG Wodehouse's Hot Water, Packy is engaged to Beatric at the opening -- she thinks she can make a man of culture out of him -- and Jane is engaged to Blair Eggleston, who writes very literary novels. They both get out of them.
 * Anna Karenina

Live Action TV

 * Gossip Girl has that in a way: Blair chooses Nate (the good guy) over Chuck (the bad guy) even though the former cheated on her with her best friend (whom he was actually in love with) and the latter was always there for her and showed a hitherto-unknown human side when he started to like her.
 * Friends, in the Backstory, features Rachel choosing Chip instead of Ross (she reveals in the Pilot that she knew about his feelings so it's not an oblivious choice). The former cheats on her, the latter eventually (as in many years later) becomes the love of her life.
 * 90210 features a variation of this trope: after years of being a troubled promiscuous drug-addict, Adrianna realizes Navid loved her all along and only cared for her happiness, and becomes his girlfriend even though she's pregnant with another guy's baby. Later on, she leaves Navid for a rich handsome jock, only to be left empty-handed as Teddy didn't want a relationship anyway.
 * In Lois and Clark, Lois very nearly marries Lex Luthor, of all people.
 * Double subverted in an episode of The Twilight Zone. A young woman has two suitors, a rich one she doesn't care for and a poor one she does. The poor one asks her to run off with him. Her future self later chases her younger self on horseback, begging her not to marry the wrong man... the poor one, who turned out to be a money-hungry bastard and ruined her life.
 * OK, it's not romance, but isn't this the plot of EVERY CSI?
 * Also every episode of House MD. Except with diseases.
 * In Republic of Doyle, Rose's first husband was a con artist. She found the right guy after he went to jail.
 * In Glee, Rachel chooses bad boy Jesse first. No one was surprised when he treated her like crap after he got what he wanted out of her  He still egged her, though, which was definitely the asshole thing to do. Later she and Finn (who has been teased all season long) get together.
 * In Vicar Of Dibley, Geraldine falls for David's brother, the cad, Simon. She ends up marrying the accountant Harry.
 * There was a male version on Skins, with Chris initially going after Angie, his psychology teacher. As you can expect with a Teacher Student Romance, it didn't end well. So he ended up with his best friend, Jal, who was willing to be there for him.

Theatre

 * In Cyrano De Bergerac, Roxanne falls in love with handsome, well-intentioned but vapid Christian because Cyrano (thinking he doesn't stand a chance with her and Playing Cyrano) wrote Christian's love letters for him. Really, it was Cyrano she was in love with all along.
 * Averted in, of all places, Romeo and Juliet. Juliet never gives the obviously richer and parentally-endorsed Paris a thought. This ends badly, and, at least according to the standards of the time, she probably should have married Paris. But then the families would still be feuding, so yeah...
 * Of course, Romeo himself was pining for Rosaline before he became enamoured of Juliet.
 * Hedda Gabler, by Henrik Ibsen, has an inverse version in the backstory: Eilert Lovborg was a Dogged Nice Guy to Hedda before he fell in love with Thea Elvstedt. Hedda supplies a tweaked example: she got married to George Tesman, who is incredibly stupid (in an intellectual sort of way), and thus, for her, the wrong guy. She gets some severe UST with both Eilert (the right guy) and Judge Brack (the even wronger guy). In the end, Eilert accidentally shoots himself and Hedda becomes a hero.
 * Happens after a fashion in Brief Encounter by Noel Coward (and the 1945 film adaptation). Laura and Alec's many happy hours spent together make it clear that each is the other's true soulmate. However, both are already married, Laura to the kind yet bland Fred, and after they are nearly caught on the brink of consummating the affair, they decide they must part ways. At the end of the play, Alec takes a job in South Africa and Laura returns to Fred (who seems to know what has been going on but accepts it).

Video Games

 * In Final Fantasy VIII, Squall's love interest Rinoa has had a previous relationship with Seifer, Squall's rival.

Western Animation

 * Sam in Danny Phantom already harbored a crush on Danny throughout the entire series, but the first boy she dated and kissed (legitimately) was the Fauxreigner Gregor, an Ultra-Recyclo Vegetarian Goth like her. Naturally, it was love at first sight (although part of the reason is that at this point, Danny was unreachable romantically for her--his heart was still set on Valerie). She finds out though that he's really just a con artist who wanted to get in her pants. She goes back to crushing on Danny and as bonus points, Danny starts realizing he likes her.

Real Life

 * Richard Gere.
 * Warren Beatty was THE womanizer before Annette Benning came along.
 * You will most likely date a few people before you find the one whose right for you.