"There is always the one girl out there, though, the one that got away. Guys have that... and serial killers have that, the one that got away. 'I had her, the trunk was lined with garbage bags, and then she got away.'"
A character once had a great love in his life, but that was a long time ago. Somewhere along the way he lost her, often without even realizing at the time what he was ever giving up. Now all he has left are bittersweet memories. Second Love often has a bitter time getting him over it.
If the lost love does ever turn up this is Old Flame, or one of its subtropes, instead.
Sister trope to Did Not Get the Girl, only here we never even meet the girl (in the present anyway, flashbacks are allowed). See also The Lost Lenore, who is lost because (s)he's dead.
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Hatori in Fruits Basket. When he told Akito he wanted to marry Kana, Akito freaked out so badly that he blinded Hatori in one eye. Kana was so distraught over this that Hatori had to erase her memories of their relationship.
A strange case in Ano Hana. We do see the girl, Menma, but only her ghost. After her death, Jintan all but gives up on life and becomes a recluse while Yukiatsu distances himself from most of his friends and cross dresses as her.
Sam the Lion and his "young lady" in The Last Picture Show.
You wouldn't believe how this country's changed. First time I seen it, there wasn't a mesquite tree on it, or a prickly pear neither. I used to own this land, you know. First time I watered a horse at this tank was - more than forty years ago. I reckon the reason why I always drag you out here is probably I'm just as sentimental as the next fella when it comes to old times. Old times. I brought a young lady swimmin' out here once, more than 20 years ago. Was after my wife had lost her mind and my boys was dead. Me and this young lady was pretty wild, I guess. In pretty deep. We used to come out here on horseback and go swimmin' without no bathing suits. One day, she wanted to swim the horses across this tank. Kind of a crazy thing to do, but we done it anyway. She bet me a silver dollar she could beat me across. She did. This old horse I was ridin' didn't want to take the water. But she was always lookin' for somethin' to do like that. Somethin' wild. I'll bet she's still got that silver dollar.
Mr. Bernstein: A fellow will remember a lot of things you wouldn't think he'd remember. You take me. One day back in 1896, I was crossing over to Jersey on the ferry and as we pulled out there was another ferry pulling in and on it there was a girl waiting to get off. A white dress she had on. She was carrying a white parasol. I only saw her for one second. She didn't see me at all, but I'll bet a month hasn't gone by since that I haven't thought of that girl.
Harry: You know the high school girl you had a crush on? The one that got away, and haunts you for the rest of your life? Gay Perry: Yeah, I've had that. Bobby Mills.
Anna in Out Cold, a pretty French girl who Rick meets while vacationing in Mexico. Even though it turns out that she's engaged and was all along, Rick still pursues her and ignores Jenny, a local girl who's clearly far better for him.
The whole plot of Chasing Amy is the unfolding events of how a girl becomes this to the protagonist. The title of the movie itself is presented as another way of saying "The One That Got Away", and this trope could in fact be renamed to that with little difference in meaning.
Silent Bob: So there's me and Amy, and we're all inseparable, right? Just big time in love. And then four months down the road, the idiot gear kicks in, and I ask about the ex-boyfriend. Which, as we all know, is a really dumb move. But you know how it is: you don't wanna know, but you just have to, right? Stupid guy bullshit. So, anyway, she starts telling me about him... how they fell in love, and how they went out for a couple of years, and how they lived together, her mother likes me better, blah, blah, blah, blah, blah... and I'm okay. But then she drops the bomb on me, and the bomb is this: it seems that a couple of times, while they were going out, he brought some people to bed with them. Menage à trois, I believe it's called. Now this just blows my mind, right? I mean, I am not used to this sort of thing. I mean, I was raised Catholic, for God's sake.
Jay: Saint Shithead.
Silent Bob: So I'm totally weirded out by this, right? And then I just start blasting her. Like... I don't know how to deal with what I'm feeling, so I figure the best way is by calling her a slut, right? And tell her she was used. I'm... I'm out for blood. I really wanna hurt this girl. I'm like, "What the fuck is your problem?", right? And she's just all calmly trying to tell me, like, it was that time and it was that place and she doesn't think she should apologize because she doesn't feel that she's done anything wrong. I'm like, "Oh, really?" That's when I look her straight in the eye, I tell her it's over. I walk.
Jay: Fuckin' A!
Silent Bob: No, idiot. It was a mistake. I didn't hate her. I wasn't disgusted with her. I was afraid. At that moment, I felt small, like... like I'd lacked experience, like I'd never be on her level, like I'd never be enough for her or something like that, you know what I'm saying? But, what I did not get, she didn't care. She wasn't looking for that guy anymore. She was... she was looking for me, for the Bob. But, uh, by the time I figure this all out, it was too late, man. She moved on, and all I had to show for it was some foolish pride, which then gave way to regret. She was the girl, I know that now. But I pushed her away. So I've spent every day since then, Chasing Amy ... so to speak.
City Slickers Mitch asks Curly the cattle boss if he's ever been in love:
Curly: Once. I was driving a herd across the panhandle. Texas. Passed near this little dirt farm right about sundown. Out in the field was this young woman, working down in the dirt. Just about then she stood up to stretch her back. She was wearing a little cotton dress, and the settin' sun was right behind her, showing the shape that God had give her. Mitch: What happened? Curly: I just turned around and rode away. Mitch: Why? Curly: I figured it wasn't gonna get any better than that.
In Hot Tub Time Machine Adam views his old girlfriend Jenny as this. But once he goes back in time and starts hanging out with her again it's easy to see why he broke up with her. Then he becomes depressed about it, especially after finding out she was originally gonna dump him, believing the choices he made in his life are pointless.
Believe it or not, Muriel Finster was this in Recess: School's Out. When she, Prickly and Benedict were young, she used to date Benedict. However, due to his desire to boost test scores by getting rid of recess at their school, she broke up with him. Because Benedict genuinely had feelings for Muriel, he never dated another woman.
The Chronicles of Fate: Josh and Jen throughout the early part of the metaplot (mostly only gone heavily into in the novels and a few published adventures, but it's a very intense invoking of this trope). Eventually they do get back together, and it becomes New Old Flame (but of the non-putting on a bus variety) and then a Tangled Family Tree sort of deal similar to Zeus and Hera, and, oh yeah, they're both actually two parts of the same person (or God, technically) so it's Selfcest as well, but it definitely starts out with many long years of Josh pining over Jen, The One That Got Away.
In A Scandal in Bohemia, Watson seems to suspect that Irene Adler is this to Sherlock Holmes, being the only woman who's managed to outfox him (she got married to someone else shortly afterwards). The fact that Holmes won't ever refer to her by name, instead calling her "the woman", doesn't prove much.
Lily Evans is this to Severus Snape in the Harry Potter series.
In A Song of Ice and Fire, Tyrion Lannister has this to his first "wife". He saves her from brigands, falls in love with her and marries her. Then his father Tywin reveals to him that she is actually a whore hired by him to teach him a lesson, has his entire guard rape her, pays her, then sends her away. This leads Tyrion to never love any woman any more, going with whores instead. Later it is revealed that she wasn't actually a whore, it was just a lie (or, as generously as possible, a Jedi Truth) by Tywin to humiliate him.
30 Rock: When Floyd came back to visit, Liz tried to invoke this trope ("The next time Floyd brings some corn-pone tranny back to his apartment, all he's going to be thinking about is me standing there in the snow looking like the one that got away."), but largely failed.
One episode of House has Wilson tell Taub and Kutner about House's "one that got away". Turns out he was just screwing with them - he even gives the woman's name as "Irene Adler." House actually did have a The One Who Got Away in Stacy who he rejected anyway after realizing that he could never love her like her husband Mark could.
Castle has one in Kyra in the episode A Rose For Everafter, much to Beckett's chagrin, though she won't admit it.
Not that Castle is pining away for her and abstaining from love entirely. Oh, no.
Season 2 of Californication features Lew Ashby, a music mogul, who got so wrapped up in the fame and the money that he lost his girlfriend, Janie, who got married to some Jerk Ass. Hank even tells Lew that Janie is his "Daisy Buchanan," and the whole season is basically a Whole Plot Reference to The Great Gatsby. Up to and including Gastby/Ashby's death.
Surprisingly, Belle is this for Rumplestiltskin in Once Upon a Time. It tortures the latter even in their new lives. They eventually start a relationship in season 2.
Ted and Victoria in How I Met Your Mother. They became a couple twice but ultimately they couldn't be together as the latter wanted the former to cut ties (cease being friends) with Robin (the person Ted left her for in their first time as a couple), which he couldn't.
A large part of Ted's Character Development in the later seasons comes from him realizing that Robin was NOT this trope. They were two people strongly committed to their priorities and their priorities were incompatible. Ted wanted to settle down and have kids while Robin wanted to travel and had absolutely no interest in being a mother. If they tried to make the relationship work, one or both would have to sacrifice their dreams and they would just make each other miserable. The series finale shows that ten years later, with their dreams fulfilled, their priorities have shifted enough that they now have a chance for a lasting relationship.
Katy Perry has a song of the same title, and the lyrics play the trope straight. The music video, however, is more of an example of The Lost Lenore.
A few of Pink Martini's songs feature this trope, most notably "Kikuchiyo To Mohshimasu," "Veronique," "The Gardens of Sampson and Beasley" (which actually manages to be pretty upbeat about it all) and possibly the tragic "Piensa en Mi."
''The Man That Got Away" was written by Harold Arlen and Ira Gershwin for the 1954 film "A Star is Born". While the original Judy Garland recording is the most famous, it has been covered by many artists, notably in a gender-flipped version ("The Gal That Got Away") by Frank Sinatra.
"Hold on Loosely" by 38 Special is sung by a guy who pushed away the girl he loved, looking back on his mistakes. "Usually it's too late when you realize what you had."
Jenny Lou Carson's "Jealous Heart", which is about a woman who drives her boyfriend because she can't control her jealousy and says the memory of him will haunt her for years.
"Strawberry Wine" by Deana Carter is told from the POV of a teenage girl who fell in love with (and lost her virginity to) one of her grandfather's farmhands when she spent the summer there. In the fall, her boyfriend had to go back to college, and though they tried a Long Distance Relationship, it didn't work out. Many years later, she still comes back to the particular spot where she lost her virginity just to reminisce.
One Touch Of Venus: The reason that modern art collector Whitlaw Savory buys a 3000-year-old Anatolian statue of a goddess is that it reminds him of "the girl who got away." When Savory runs into the goddess wandering through the Big Applesauce, he recognizes her as The One That Got Away, not as his missing statue.
Red vs. Blue: The Director of Project Freelancer is so haunted by the memory of a lost love that he ends up in a perpetual cycle of losing her over and over again, via the AI he created (a Living Memory of his own experiences) and the Virtual Ghost that the AI creates in the image of the Director's lost love.
On Adventure Time, Betty is this for Simon, aka the Ice King. It's tinged with The Lost Lenore as well, since she would presumably have died centuries before the show's setting. As it turns out, Betty jumped through a time portal opened by a temporarily sane Simon attempting to communicate to her and by the end of the episode is still out in Ooo, seeking a way to cure him of his insanity.
Bobby Darin was this for singer Connie Francis. According to her autobiography, her Overprotective Dad kept them apart, and she claimed not marrying him was one of the biggest mistakes of her life.