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Winner Sinclair is an anime only character and is not included the manga. Winner is a Vampire Hunter in training. He is also hemophobic, and falls in love with Karin at first sight (without knowing she is a vampire).

Winner thinks that Karin was his first kiss, about 4 to 6 years ago, when actually Winner Sinclair was the first person Karin bit after awaking as a vampire. He confused it with a kiss because his memory wasn't erased completely. He remembers that day.

Maki Tokitou is in love with Winner, and she keeps getting denied by him. For instance, Maki was going to give him a hand-made scarf for Christmas and tell him the truth, but he was in a hurry and told her "can you save such trivial matters for later"... and she fell apart.

Later, Winner figures out that Karin is a vampire. His grandfather told him the truth about the event of his "first kiss," and his grandfather told him to kill Karin and her grandmother. He couldn't do it since he loved her to much, and gave them time to run. Later, he meets up with Maki and talks to her about it and now Maki knows that Karin is a Vampire and the one thing she says is "Karin is still Karin." This helped him get over the new news and went to save Karin from his grandfather.

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