20 Most Cringeworthy Star Trek: The Next Generation Moments

19. Geordi's Attempts At Romance

It's a toss-up between 1989's unfortunately-named Booby Trap and 1990's Transfigurations as far as which episode serves up the most cringes, though Geordi's romantic misadventures are by no means limited to these two. Our long-suffering Chief Engineer has made several attempts to alleviate his loneliness with an assortment of fake, dead, and/or married people, and these attempts range from the merely embarrassing to the downright painful. In the former category, it's Geordi's attempt to woo Christy Henshaw on the Holodeck with a beach, some fruity drinks, and an even fruitier violin player. Unfortunately, Geordi gets friendzoned fairly quickly, leading to a vastly uncomfortable silence that can't be ended by simply ending the programme because they're filming on location. But if she likes him only as a friend, why go on the damn date to begin with? In the latter category, it's the moment in Transfigurations that Leah Brahms, of whom Geordi created a fully functional copy on the holodeck, discovers her doppelganger and brings the hammer down. Here, of course, the discomfort is to some degree intentional - Geordi's been a bad boy, and we're meant to feel he's somewhat getting what he deserves. But Susan Dibney's delivery of the line "Was it good for you?" pushes it over the line from earned discomfort into unintended discomfort. Thing is, when we consider that Leah's gotten a lot of calls from home while on Enterprise, we wonder if she's got an overly jealous hubby back home who's causing her to be so bitchy. No wonder we're relieved that Geordi's married to her in an alternate future timeline - he probably saved her from a really bad marriage.