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This is a movie I never watched but read about while I was busying myself reading plot summaries on Wikipedia. I probably read it some time around 2015 but I think the movie came out somewhere between 2000 and 2010.

The movie included several horror stories that happened during Halloween. Although I only remember one story, I think there was very little connection between each of them.

The story I remember had a man and a woman who seemed to be about to make out. However, after the man approached the woman's neck, to her horror, instead of kissing her, she noticed he had bloodied teeth, as if he was a vampire (although I think he was a serial killer disguised as a vampire). As she attempted to run away towards a huge crowd celebrating Halloween to ask for help, the man caught her and finished her off in an alleyway.

After that, the story focused on 4 young women. The way the summary told it, one of them was forced by the 3 others to wear a red riding hood disguise as a prank, because she was still a "virgin" (the word was purposely quoted for reasons you will understand at the end of the story). The red riding hood wasn't very thrilled about the idea of enjoying the party, whilst the 3 other went on to find some boys with whom to spend some time.

At some point during the story, the disguised vampire from before decided to attack the woman with the red hood. And because of her attire, before attacking her, he told her: "My, my, what big eyes you have".

Later on, the same serial killer disguised as a vampire was begging for help from the other women. Apparently, he was scared for his life. At this point, we learn that all 4 women actually are werewolves, the boys they picked for a date are victims, and the reason the red hood was called a "virgin" was because she never killed anyone yet, because she didn't want to kill innocent people. But since this man is a serial killer, she decided that she would kill him.

The story ended with all 4 women turning into werewolves to kill their picks. But before killing the serial killer, the red riding hood looked at him and retorted: "My, my, what big eyes you have".

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This sounds like it could be Trick 'r Treat. It's a horror anthology film released in 2007, and appears to match most of what you describe.

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The plot, courtesy of Wikipedia:

The film takes place on Halloween night in the fictional town of Warren Valley, Ohio. The plot follows a nonlinear narrative, with characters crossing paths throughout the film. At the center of the story is Sam, a peculiar trick-or-treater in an orange footie pajama costume, who appears to enforce the "rules" of Halloween.

The Little Red Riding Hood bit that you mention could be the chapter "Surprise Party":

Laurie, a self-conscious 22-year-old from out of town, joins her older sister Danielle and friends Maria and Janet for Halloween. The girls all select fairy tale princess costumes, encouraging Laurie to wear a "Little Red Riding Hood" costume. A devout Halloween traditionalist, Laurie misses trick-or-treating and is uncaring of her friends and sister's talks of dates.

While the other girls pick up dates and head to a party in the woods, Laurie chooses to stay and enjoy the town festival instead. Later, on the way to meet up with her friends, she is attacked by a hooded man dressed as a vampire. A bundle of red cloth later falls out of a tree by the girls' bonfire, revealing the injured and frightened vampire. After an arriving Laurie remarks that he bit her, Laurie's friends unmask the man, revealed to be Steven Wilkins, who had been seeking out victims at the festival.

Laurie's sister and friends all shed their clothing and skin and transform into werewolves. With it being her first time killing someone, and having sought out someone who deserves it, Laurie transforms and slaughters Wilkins before devouring him. Sam, sitting on a nearby log, watches as the werewolves feast on their deceased dates.

Here's a clip from the movie, showing the scene where the vampire says "My, my, what big eyes you have" (around 1:15):

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  • It looks like the plot summary on Wikipedia drastically changed since the last time I read it, but it definitely sounds like this is the one.
    – Clockwork
    Feb 23 at 13:21
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    @Clockwork it looks like the Wiki page has had some heavy editing done over the last year or so. It's also possible you read the Villains fandom entry at the same or similar time? That one follows a bit more closely to what you recall that the Wikipedia page
    – fez
    Feb 23 at 13:31
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    Based on the date at which that fandom page was written (30th January 2015), I went looking at the older revisions from Wikipedia, and I found a version which is closer to what I read back then, dating back to 2016 (the revisions from 2015 and earlier had some mention about her "virginity" but didn't have the big eyes quote). Edit: I found the first revision with the version I read back then.
    – Clockwork
    Feb 23 at 13:46

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