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Answer for the clue "Terrible wingman, slangily, hiding literally twice in this puzzle ", 9 letters:
cockblock

Word definitions for cockblock in dictionaries

Wikipedia Word definitions in Wikipedia
Cockblock is a slang term for an action, intentional or not, that serves to prevent someone from having sex . Such behavior is often motivated by jealousy, or competitiveness, although it is sometimes accidental, or inadvertent. A cockblock or cockblocker ...

Wiktionary Word definitions in Wiktionary
n. 1 (context vulgar slang English) A person who deliberately or inadvertently makes impossible another's intended goal of sexual intercourse. 2 (context vulgar slang by extension English) Something designed to prevent one from achieving a goal (e.g. an ...