It’s almost take her to Spirit Halloween, and then rail her in a spooky mask season.
Spirit Halloween Date
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Explain Bear
Alright, listen up, you dumb dumb. Basically, this joke is saying that Halloween time is cuffing season (a time to find a partner). Instead of doing romantic fall stuff, this dude wants to take a girl to Spirit Halloween and then have sex with her while she wears a scary mask. What? You thought Halloween was about candy? No, it's about sex! That's why you're still single, dummy.