I'm looking for characters that kind of um, "fake smile", or even appear to be nice/friendly when they're not at all or just the opposite. They are thinking something completely different but smiles on the outside, while feeling something totally different in the inside. Or a character that hides thing by acting nice and smiling all the time, but is different. Maybe even a vague or negative character that smiles to act in favor of a situation, or a person who smiles and talks his way out to avoid difficult situations or to cover himself up.

Or he appears to be nice and friendly but is actually a pessimistic or negative or apathetic character. There's more "situations" but you basically know what I'm looking for, so thanks ahead of time. Looking for preferable male mains who do this a lot.

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Death Note for sure.

Akuma to Love Song, but it's only 1 of the male leads.

and maybe Hot Blooded Woman and Beelzebub since she tends to do that when they're about to beat someone up?

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The main character and his father in Zippy Ziggy.

Skip Beat! Ren

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http://westsiders2.deviantart.com/

Naruto Sai



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*__* I'll have what she's having... please~♥

It doesn't look like it, but Fai from Tsubasa Reservoir Chronicle is often wearing a fake smile.

The same could also be said of Shizumasa from Shinshi Doumei Cross in the beginning.

Perhaps Yukino (heroine, though) from Kare Kano? Though I haven't read much of the story to know how far it continues.

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If you've ever thought or said "Nice Guys finish last" and really meant it, then you should probably read this LJ post by DivaLion. It's incredibly insightful whether you're male or female.

From a bumper sticker I like:
"If you're gonna ride my ass, at least pull my hair."

Shoujo:
You're So Cool - the guy is so evil...
Koukou Debut - in the case of the guy's best friend (they dwell on it later in the story)
Vampire Game - in the case of the braided guy
Kamikaze Kaitou Jeanne - in the case of the main heroine
Kare Kano in the main couple's case
Special A - in the guy's case

Shounen/Seinen:
Apple (KOMI Naoshi) - though I'm not sure if it's fake, he's always smiling
Majin Tantei Nougami Neuro - in Neuro's case xD
Monster - in Grimmer's case, really great read, too =)

Ningyou Kyuutei Gakudan Lucille
Monochrome Factor Shirogane (sorta, he loses it quickly)
Host Club sorta in the love triangle and Tamaki in the later chapters
Bokurano one of the pilot girls...I forgot her name
Alive: The Final Evolution has another girl like this in the first arc...I think her name was kanon

Dragon Eye - He hides things by smiling/acting silly all the time.

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Antique Bakery
"Bungaku Shoujo" to Shi ni Tagari no Douke
Full Metal Alchemist - Pride
Heart no Kuni no Alice
Historie
Kuroshitsuji
Obaka-chan, Koigatariki

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Avatar by tassyn.livejournal.com

Reading: Kingdom, Sangokushi, Historie

Might not be your cup of tea but . . .

Kimi wa Boku no Toriko Nare Tomoe.

Only Code:Breaker comes to my mind that hasn't been mentioned yet

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Sorry for my english xD

The first one that comes to mind is 1/2 Prince.
I'll add more when they come to mind.

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"Officially, this machine doesn't exist, you didn't get it from me,
and I don't know you. Make sure it doesn't leave the building."