20 Most Cringeworthy Star Trek: The Next Generation Moments

6. Riker's Glittery Pajamas From Angel One (1988)

Yar's expression in the image above says it all, though we really hope she's not looking at what we think she's looking at. The smirks on the faces of Yar and Troi mirror what many of us felt when we first saw Angel One, though it mainly just made us sigh in frustration. Much like The Outcast, this episode tries to address the controversial concept of gender roles and does it in a way that couldn't be more offensive if everyone dressed up in blackface. Sadly, they'd already offended the audience that way (as we'll get to soon enough). Naturally, we can't have Riker walking around being manly on the Planet of Amazon Women and Fey Men, so Riker has to don some sparkly pajamas about midway through the episode to be socially acceptable. We suspect this was meant as fan service for the heterosexual women (and gay men) in the audience, but it just ends up looking silly.