Yousuke is the quintessential loser. Whenever something bad can possibly happen to him, it usually happens. He's awkward, he's clumsy, and for some reason, he tends to get frequently injured in freak accidents that can be attributed solely to bad luck. Due to all of these terrible qualities, Yousuke firmly believes the world, nay, the universe itself is out to get him, just for a laugh. He's definitely a 'glass is half empty' kind of guy in almost every situation.
Despite all this, Yousuke isn't as emo as one would initially expect. He keeps an upbeat, happy attitude, spiked only occasionally with bouts of extreme cynicism. He's learned to laugh at himself, twisting his awful luck and tendency toward injury to make himself look like a bit of a clown. This image is carefully cultivated, sometimes on purpose and sometimes entirely by accident. He puts on a happy face for the world around him, especially for strangers, and is swift to attempt to move in and turn a person from an unknown into a friend. Once he's decided he likes you, Yousuke will stick by you for life, or at least until he gets some sort of clue that you don't actually like him all that much.
Deep inside, though, Yousuke is terribly lonely, with little aptitude whatsoever toward actually connecting to anyone beyond a superficial level. Yousuke doesn't want attention so much as he needs it: to be the center of everyone's world and the guy everyone knows they can always turn or look up to. Unfortunately, he lacks significant social skills and has a hard time opening up to show someone how he really is. People are frightening when you start getting into the little details of your life, and though he'll do everything he can to get you to pay attention and speak to him, he'll be on tenterhooks the whole time to make sure it's a positive impression.
When he lived in a big city, before moving to Inaba, Yousuke was able to drown out his loneliness by surrounding himself with people. In Inaba, a tiny, tiny town, he couldn't do this anymore. There just weren't enough faces to go around, and to top that off, many people outright hated him for his father's store. Though he formed a couple friendships with a handful of people, there were frequent times when he was absolutely crushed by the feeling that he was alone in the world. Thanks to his true bonds with Souji Seta and the other members of the Investigation Team, his issues concerning being alone have taken a mighty beating, but he's still the kind of guy that will go to a party, invited or not, just to be around as many people as he can.
While canonically possessing a Persona called Susano-o, Yousuke has lost access to him as his Permanent Loss.
Yousuke is a skilled fighter, capable of doing moderate melee damage with a pair of short weapons. These range from daggers and knives to kunai to even wrenches. His patented move, the Yousuke Strike, sends him into a whirlwind of steel (or whatever his current weapon is made of), inflicting high damage, but is ridiculously impractical and useless against foes that aren't already stunned.
CHIE→ Crushed on her for a while. Pretty much over it. A really good fran, now.
KANJI→ Kind of scared of him. No offense meant, big guy, just stay out of his tent.
NANAKO→ D'aww man, Nanako's so cute! He'd seriously be happy to be her big brother if she didn't already have one.
NAOTO→ It's. It's Naoto-kun! She appears to have forgotten pretty much everything she did with the entire gang, but that's no reason to get upset.
SOUJI→ Mrrrr. He wants to get things back to normal with Sooj, but killing Chie and trying to kill Nanako makes some significant roadblocks. They have to see...
YUKIKO→ Failed the Amagi Challenge before he even started. She punched him in the face when all he wanted to do was study with her. Still, she's a very dear friend.
ERICA→ What a silly girl, thinks she's an airforce pilot, hohoho.
MINATO→ Why do we have the same voice. Seriously it's kinda weird. Oh well, still a nice guy.
SAKAKI→ Kind of a confusing girl. Very sweet, but seems... sad? Distant?
GINO→ Is a bro. Promised to take him for a ride in a giant robot some day, which is awesome.
KALLEN→ Surprise girlfriend! Started off afraid of her after he got caught checking her out, but they became friends, and one thing led to another pretty quickly. He's downright crazy about her now, but constantly worried he's going to screw up.
MAT→ Is also a bro. Kind of funny the way he reacts to everything modern, but as a fellow explosions enthusiast, he's definitely alright.
EUNICE→ Nicest gal in her thirties he's ever met. Yosuke really feels like he can trust Eunice. He also thinks she's hot, but shh.
INO→ Sensei! She's cute and funny and nice, too, always good things.
SORA→ A derpy, derpy kid alright. But, he's alright. Could be bro status.
MINKY→ Nice girl. Hamster-like, for some reason. Kinda feels bad about how weird it is for her with her friends here.