Others... not so much. They may be clumsy, kooky, not socially connected, poor, powerless, but whatever the reason, they're not someone an impressive person (often but not necessarily The Hero) would ever hang out with, right?
An outsider (sometimes but not necessarily the Big Bad) often can't stop questioning how this person got on the more impressive guy's radar. Surely he could do better. They may claim that the "loser's" reputation for being friends with the "superior" person must be false or (if the respected person confirms it) criticize him for his choice in company. In some cases (usually a story where the Aesop is the dangers of trying to fit In with the In Crowd), the non-loser character will buckle to it and try to end or downplay the relationship. However, in time he'll (usually) come to his senses, often giving a speech as to just why he thinks this person is worth his time. He may mention that his friend has his quirks, but he's kind, loyal, generous, or some other quality that makes him a good friend.
Depending on the story, the relationship may be an explicitly Forbidden Friendship; in others, it's just understood that certain people aren't supposed to hang out together. As with the romantic version What Does She See in Him?, it should be noted that, given that different things are valued by different groups, which friend is the "loser" might vary based on the environment.
This trope tends to fall on the middle to more idealistic side of the Sliding Scale of Idealism vs. Cynicism.
This may overlap with The Friend Nobody Likes. However, in that trope, the whole social circle hates the "loser" rather than an outsider to the group, and the person may actually have some cause for being disliked. Here, the person is usually presented as being an innocent victim of prejudice, whether it's related to social Darwinism, jocks vs geeks, Slobs vs. Snobs, or racism, fantastic or otherwise.
- In Fruits Basket, the student body know nothing about the Sohmas' Big, Screwed-Up Family, and consequently wonder why so many Sohmas go out of their way to befriend Tohru. Yuki Sohma explains why the students feel this way: on the outside, Yuki is a handsome School Idol who all the girls admire; on the inside he is a disillusioned, self-loathing mess of neuroses.
- In Goblin Slayer, the titular character attracts derision from other adventurers and the general public due to his attitude and eccentric appearance. This gets worse when he is around beautiful girls like Priestess, Cow Girl and High Elf Archer, because others assume the only reason why they would associate with him is through some sort of dark secret or coercion rather than genuine respect, affection or infatuation.
- In Kaiju Girl Caramelise, Raimu "Rairi" Kouno is The Fashionista who became popular thanks to her good looks and willingness to give other girls fashion advice. Kuroe Akaishi is a nearly friendless, socially awkward girl who regularly gets shunned by her classmates. So when Rairi gives Kuroe an impromptu makeover upon their first meeting before proudly introducing herself, their onlooking classmates are astonished. Kuroe herself is similarly surprised when Rairi unhesitatingly agrees to go makeup shopping with her later that day. It's revealed that Rairi's backstory is pretty similar to Kuroe's, which explains her desire to help Kuroe avoid the kind of pain she went through.
- Yes! Pretty Cure 5s Five-Man Band includes the ace of the schools futsal team, an up and coming actress, the beloved Student Council President, and her childhood friend who works at the school library. And everyone is perplexed by how these four extraordinarily popular girls seem to gravitate around Nozomi Yumehara, The Ditz who is notorious for having been kicked out of every club for her sheer uselessness.
- In an old Jimmy Olsen comic, a teenage lifeguard scoffs, "Superman's pal! How did he get that reputation?" Fortunately, Jimmy is nice enough not to taunt him about it when the relationship is eventually confirmed.
- As a result of Roy Harper being turned into a moron thanks to the New 52, he became the Loser Friend portion of this trope to Jason Todd in Red Hood and the Outlaws. Even after Roy dies in Heroes in Crisis, Jason's told by Batwoman and Damian Wayne that neither of them understood why he was ever friends with Roy.
- Robin Series: Local Jerk Jock Karl Ranck tries to pry Tim away from his friends by insulting Ives and Hudster as "geekoids" and repeatedly telling Tim that Tim is better than them. These pathetic attempts seem to be rooted in Karl wanting to make connections with one of the richest kids in school. Tim responds that he'd much rather have actual friends than hang out with the most "appropriate" clique for someone of his family background.
- In Get Smart, Larrabee wonders why the cooler Agent 23 is friends with Maxwell Smart.
- To Have and Have Not: Bogart's character is friends with a not too bright drunkard who always begs Bogey to give him some money so he can visit a bar. Nobody understands why he keeps having contact with this loser, but Bogey explains that the man once helped him out in the past and now he feels responsible for him.
- In Sky High (2005), students are segregated by class (no, not that kind of class). "Heroes" (the kids with conventionally useful powers) are treated as- and believe themselves to be- superior to "Sidekicks" (everyone else). When the "Hero" protagonist befriends several "Sidekicks", it bemuses the other "Heroes".
- In Of Mice & Men everyone wonders why such a normal guy like George hangs out with a big dumb brute like Lennie. George claims (falsely) that they're cousins to give people an easy reason to understand.
- Harry Potter:
- Harry's friendship with Neville and Luna. She says "People expect you to have cooler friends than us." He replies that they are cool. "I didn't see any of them fighting alongside me at the Ministry last year."
- Gryffindor reactions to Snape in regards to his childhood friend Lily who was popular in school.
- Played With example from How to Cheat a Dragon's Curse. Hiccup, a weedy Guile Hero son of a dragon-killing chieftain, is friends with Fishlegs, a likewise weedy teenager. In spite of his weakness, the fact that Hiccup is a chief's son makes him slightly better than Fishlegs socially, and Stoick, Hiccup's father, urges his son to "give him up." He eventually says he was mistaken about Fishlegs.
- Sherlock Holmes subverts this in "The Boscombe Valley Mystery." Two former Australians, John Turner and Charles McCarthy, are apparently such good friends that John is letting Charles live on his land for half-rent, and there is even talk of their children marrying. McCarthy is actually blackmailing Turner due to a robbery he committed in the past, and the marriage, while mutually agreeable to both children, would have allowed McCarthy to control Turner's money.
- In Afternoon of the Elves, Sara-Kate is a badly-dressed, strange girl who happens to live near Hillary. Nobody can figure out why Hillary enjoys Sara-Kate's company, or vice versa, and Hillary's friends and family actively try to pry them apart. Even the girls themselves are a little bewildered by their own friendship, at times.
- Grey's Anatomy's "Things We Said Today" has Owen confused as to why the biker gang allows short, nerdy, clumsy Stewart to hang out with them. It turns out, he started as their accountant and they took a liking to him, almost as a mascot.
Owen: "You're going to have to explain Stewart to me."
- One Midsomer Murders episode has an old homeless guy accused of murdering a young man. His friend, the local lord, declares himself his legal counsel to get Troy out of the way. Lampshaded by a guy at the pub, who says:
You'd think he could find a better friend than a former appeals court judge.
- Noah and Saskia lampshades this trope. Saskia envisions the mental landscape of Renee - a wealthy fashionista with straight-As - as a glamorous store filled with giant metaphorical price tags. One of these tags is 'No loser friends except for Saskia'.
- One episode of Seinfeld inverts this with the Girl of the Week that Jerry is dating, who seems perfectly normal... except that every single person other than Jerry thinks she's a huge loser for no apparent reason. Her friends basically call Jerry a saint for dating her, as if it was some noble sacrifice done out of selfless pity and compassion, while Jerry's friends stage an intervention assuming he must be depressed or fallen on hard times to consider dating this woman. Jerry is utterly baffled by this and wonders what the hell could be wrong with her to make everyone act this way. He flies in his parents to meet her, desperate to have someone approve of his relationship with this woman, and they absolutely love her... so he dumps her immediately.
- In House, Wilson is very well-liked and considered by most of the hospital to be a sensitive, friendly Nice Guy - so nobody can understand why he spends so much time with misanthropic Jerkass House. The reason is something of an inversion from most cases of this trope: rather than House being nicer than he's thought to be, it's Wilson who's much less of a good person than his reputation suggests, with only House familiar with his less-stellar qualities and able to understand him. In particular, the fact that House is so incapable of normal friendships is precisely why he appeals to him, because Wilson loves to be needed, and nobody is as determined to keep himself from ever getting better as House.
- A few characters in Ensemble Stars!, particularly Keito and Tori, cannot at all understand why the elegant, wealthy Princely Young Man Eichi values such a close friendship with the incredibly eccentric Gadfly and Large Ham Wataru. Meanwhile, many of those hurt by Eichi's Manipulative Bastard actions find it unbelievable that Wataru - who himself was also targeted by Eichi - is now so happy to play friends with him.
- Despite being very attractive, confident and socially apt, Jane from Daria prefers to be rather alone than Surrounded by Idiots. In one episode, Jane signs for auditions for the athletics team, where she is discovered to be a great athlete (jogging was always her hobby) and starts dating a popular kid. However, said guy was also a Jerk Jock who criticized Jane's best friend Daria for being a total loser. Jane then says that she realizes that she has being hanging around too much with losers, dumps her boyfriend, quits the team and keeps being friends with Daria.note
- Played with in the DuckTales (1987) episode "The Status Seekers". Some of the titular group start the episode by saying derogatorily that Scrooge doesn't act rich. After he tries to do more conspicuously high-status things and gets back the mask of Kuthu-lulu, they accept him, even making him the president of the association. When Mrs. Beakley, Launchpad, and the boys turn up to congratulate him, they push him to give them the boot, because rich people don't have friends "like that." Scrooge wavers, but after his friends and family help him during the final battle with the villains (and the status seekers refuse to "get their hands dirty"), he calls out the status seekers and ditches them instead.
- In the Dynomutt, Dog Wonder / Dexter's Laboratory crossover "Dyno-might", Dexter, recruited to fix Dynomutt after a mission gone wrong, is appalled at his ditziness (thinking he's too much like his sister, DeeDee) and creates a Darker and Edgier replacement. Blue Falcon calls him out for this when he learns, saying that Dynomutt "wasn't just a goofy idiot sidekick; he was a go-go dog person!"
- In the Hercules: The Animated Series crossover with Aladdin: The Series, Jafar comments, "This is Hercules' best friend?" upon meeting Icarus. Hercules is The Chosen One who will defeat Hades, and, in spite of his dorky nature, is a force to be reckoned with; Icarus, while he is a Gadgeteer Genius, is also a kooky Manchild.
- In My Little Pony: Friendship Is Magic, "Power Ponies", the Mane-iac mocks Humdrum/Spike, saying that the only reason they keep him around is because they feel sorry for him. Masked Matterhorn / Twilight instantly snaps, "Shut Up, Hannibal!", telling her that even if they don't always need Spike's help they have faith that he'll save them all, since he always comes through for them.