How to make a cool character who is really unmanly? The guy is bad at leadership, lacks endurance and strength while also being kind of a coward and having quite feminine facial features.
closed as primarily opinion-based by wetcircuit, F1Krazy, Cyn♦, Thomo, Lauren Ipsum Nov 9 '18 at 1:35
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Give him a talent. Make him a musician, or singer. Let him have a sense of fashion. Let him win some talent contests and awards with this talent. I'd say even a comic, but writing that dialogue could easily fall flat. I will note that many professional comics freely admit they were cowards in school, but people loved hanging with them because the comic made them laugh.
This could even be low-contact sports, a basketball player doesn't have to be a tough guy to have the highest shooting average on the team, the same goes for the shutout pitcher on the baseball team.
Pick a talent that impresses his classmates; or just the same for the writer, write his classmates as people that are fans of his talent.
He doesn't have to be brave in a physical confrontation in order to have the confidence to get on stage (or on the field) and deliver. Just like comics may run from or cower before bullies but still have the self-confidence to make an utter fool of themselves on the stage, to elicit laughter.
Ensure his classmates are impressed. Bullies may still come, but he can also be welcome amongst friends that protect him from said bullies, because they enjoy and admire what he does. They might even think he's going to be a frikkin' star someday.
Cool is confidence
Confidence may inspire people to follow you, but you don't have to be a leader to be confident.
You need neither physical strength nor physical endurance to exude confidence. Neither is a particular "look" really necessary.
Cool is level-headedness
If you're truly confident (or good at faking it), you don't lose your "cool." That means you aren't upset by little things.
Cool is self-awareness
Not the downer self-awareness of the overly taciturn, but enough awareness that you know how not to step in proverbial (or literal) dog-poop. Speaking of which...
Cool is being competent enough (in the circles you move in) that your confidence doesn't make you look absurd
So, as other people have alluded to, your cool character might need some kind of talent or competency to back up that confidence they're oozing.
And don't forget...
Cool isn't petty
You don't have to be nice to be cool, exactly. But it isn't cool to be a jerk. Unless the jerk-move you just pulled was seen (by the those thinking of you as cool) as deserved by the recipient. But if you want compassionate people to think that you're cool, you can't be too transparently unpleasant.
'Coolness' is really subjective, but depending on the definition, I can give a brief rundown of each possibility.
Coolness as talent: This is simple; if you consider being talented/skilled the 'cool' you're going for, give them a talent, as Amadeus suggested. Make it that despite his effeminate nature, he's clearly good at the things he puts his heart into; heck, maybe his effeminacy helps his talent, or at least spurs it on (akin to Billy Elliot and his ballet skill, or any guy in musical theatre).
Coolness as the ability to roll with the punches: This is the kind of guy that can adapt to anything and will rarely if ever be rattled by life. Give a story with twists and turns which will throw other characters off balance, but leave the cool guy unfazed, or at the very least, he remains functional and calm enough to come up with an alternative plan fast.
Coolness as emotional intelligence/social savvy: This guy may be effeminate, but he's also very in tune with his friends, and often knows exactly what they want, how to defuse an argument, and what points to prod to make a person do what he wants. As such, he's respected and looked up to for his social savvy.
Coolness as gentleness: Believe it or not, gentle men can be seen as some of the coolest men alive. Doctor Seuss and Bob Ross are examples of men who may not be imposing or stereotypically manly, but they do have emotional fortitude. They don't confront people; they end confrontations, and do so in a kind, calm, yet resolute manner. These are often cast into parental roles, as an example of an ideal father figure.
Hopefully this helps.
You know what famous character is not a leader, lacks endurance and strength, is not particularly brave, and has a beardless round face? Bilbo. Or Frodo, for that matter. Or Sam:
'I am sorry,' said Frodo. 'But I am frightened; and I do not feel any pity for Gollum.' (The Lord of the Rings, Book I, chapter 2 - The Shadow of the Past)
'I do really wish to destroy it!' cried Frodo. 'Or, well, to have it destroyed. I am not made for perilous quests. (ibid)
'I should like to save the Shire, if I could - though there have been times when I thought the inhabitants too stupid and dull for words, and have felt that an earthquake or an invasion of dragons might be good for them.' (ibid)
I feel very small, and very uprooted, and well - desperate. The Enemy is so strong and terrible. (ibid)
And it continues throughout the narration - Frodo is terrified every step of the way. And so is Sam. And Bilbo almost wets himself in Smaug's lair. Physically, they are the weakest of the party, they are content to let others lead, and they feel altogether inadequate for the task they've been sent to perform.
What makes them awesome is that they master their very human, very understandable fear, and rise to the occasion. I don't know if that answers your definition of "cool", but those characters are engaging, relatable, and admirable. They are very much "ordinary people", which makes their heroic acts all the more extraordinary. For all their fear, for all that they are unfit and unprepared for the task, they step up and do what is necessary. And handsome Legolas pales before them, and royal Aragorn bends his knee.
Have him sleep with a lot of women (ladies' man). He does not dress to impress "the guys". He's a lover not a fighter.
Give him a rich father and an expensive car. Most people are willing to believe their rich friends are "cool", especially when they share. You have not said who it is that is suppose to find him "cool", but this is essentially the entire plot of The Great Gatsby.
Make him anti-establishment so he is constantly calling out society for hypocrisy and self-delusions. If he seems like he is in a lot of pain and is emotionally damaged, it could explain him being a chick magnet. Most people think Jack Kerouac is cool.