A ranking catering to the darkest depths of otaku fandom has been doing the rounds, listing the top anime crossover couples (thoise with each person coming from an entirely different anime), naturally possessing a myriad of odd pairings that will probably only make sense to the truly obsessed.
1. Producer (Idolmaster: Cinderella Girls) and Sheryl Nome (Macross Frontier)
2. Kazuto “Kirito” Kirigaya (Sword Art Online) and Konata Izumi (Lucky Star)
3. Hachiman Hikigaya (Oregairu) and Tomoko Kuroki (Watamote)
4. Keiichi Nakagawa (Kochikame) and Nasuno Takamiya (Teekyu)
5. Subaru Hasegawa (Ro-Kyu-Bu!) and Elpeo Puru (Mobile Suit Gundam ZZ)
6. Hanamichi Sakuragi (Slam Dunk) and Riko Aida (Kuroko no Basket)
7. Lupin III (Lupin III) and Rinslet Walker (Black Cat)
8. Kyon (Haruhi Suzumiya) and Nobume Imai (Gintama)
9. Enel (One Piece) and Mikoto Misaka (To Aru Kagaku no Railgun)
10. Kurapika (Hunter x Hunter) and Ai Enma (Hell Girl)
There were some pairings resulting from the NicoNico Douga RPG that I thought were pretty amusing. There was Yugi Mutou+Konata Izumi, Seto Kaiba+Kotonoha Katsura, and Mega Man+Hatsune Miku, maybe others.
Speaking of games, I gotta love how the official site for both Smash Bros. Brawl and Smash 4 uses screenshots that portray Marth as a total player (though with particular emphasis on Marth+Peach).
tsuda takatoshi and kajou ayame
or if girl x girl is allowed, amakusa shino and kajou ayame
hachiman and tomoko…yeah baby, time to release the deadly aura…
Kino Makoto and Tatsumi Kanji.
Hachiman and Tomoko is a couple I could root for