Top 10 Cringeworthy Date Scenes on TV

Oh god, that is cringy. You know those dates you watch that just slowly die in front of you but you can’t look away because it’s so bad that it’s good? We’re taking a look at the Top 10 Most Cringeworthy dates on TV including Sookie and Jackson’s cousin Rune’s date, Carrie Bradshaw and Mr. Willie Applegate, a nervous graphic designer, and Liz Lemon’s hilarious date with Stew.
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Top 10 Cringeworthy Date Scenes on TV


Chaotic and comedic, these TV scenes are the antithesis of “true romance.” Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Cringeworthy Date Scenes on TV.

For this list, we’re focusing on would-be romantic small screen dates that quickly spiraled out of control.

#10: Rune
“Gilmore Girls” (2000-07)


In Season 1, Sookie St. James takes a proactive approach with her love life and lands a date with Mr. Jackson Belleville. Since Jackson’s cousin Rune is in town, Sookie looks to Lorelai for assistance, resulting in a double date. But the eccentric Rune has a few issues, as he immediately recognizes an apparent flaw in Lorelai. This woman is TALL. And so, quirky Rune essentially ruins the moment, as Sookie and Lorelai try to process it all, and Jackson attempts to minimize the drama. Some men are specific about their dating preferences, and Rune is most definitely one of those special fellows.

#9: Texting Mishap
“Love” (2016-)


The “friend zone” is never a comfortable place to be. Especially for a man like Gus Cruikshank, who inches ever so close to a relationship with the quirky Mickey Dobbs. And so, it’s already bit awkward when he gets set up with Mickey’s roommate, Bertie, and the date goes south after a rather unfortunate texting snafu. But Gus composes himself and thoroughly pushes the boundaries of acceptable dining banter. In other words, the game is on. Yet, Gus’ strategy backfires when Mickey colludes with Bertie, leading to a cringeworthy sequence of events between the two disinterested dates.

#8: Fireworks Date
“The Last Man on Earth” (2015-)


Phil needs to repopulate the earth, and that’s because, yes, he seems to be the last man on earth. Unfortunately, there’s a bit of friction with his wife, Carol, and his alluring love interest, Melissa. But the group finds a compromise with a scheduled love session, or so it would seem. On his big date, Phil begins playing a guitar, which leads not to romantic fireworks, but to literal fireworks. And so, a gentleman named Todd follows the light, so to speak, which gives Melissa another option to consider and completely wrecks Phil’s romantic plans.

#7: Worst Date
“Master of None” (2015-)


Early in Season 1, Dev needs a date after landing Father John Misty tickets. At first, Nina seems like the ideal companion – not a bad catch for Dev, actually. But when she breaks out her Eric Cartman impression, the “Master of None” discovers that Nina just may be a bit, um, unique. Goofy as Dev may be, his date’s comedy feels a bit over-the-top. Furthermore, she proves to be a kleptomaniac, too, thus destroying the Father John experience and further irritating poor Dev. For a guy looking for love, this disastrous scenario proves to have a silver lining, as it transitions directly into Dev’s relationship with Rachel.

#6: Man Hands
“Seinfeld “ (1989-98)


In a Season 8 episode, Jerry once again has some personal dilemmas. Perhaps the most cringeworthy moment comes when he meets a beautiful woman named Gillian. She’s got a massive set of hands - at least according to Jerry - and he can’t help but hear every amplified sound when she crunches a big ol’ lobster. As far as “deal-breakers” go, it’s surely not the worst flaw to muddle on. Then again, nobody wants to have an awkward dining experience thanks to some “meaty paws.” For Jerry, the Man Hands take over his thoughts, much like what happened to Elaine when her date “took it out” in Season 5.

#5: Full On Rapist
“It’s Always Sunny in Philadelphia” (2005-)


After learning that Charlie’s love interest is getting married, the gang tries to get him back on the dating scene. However, numerous factors contribute to a seriously disturbing appearance, such as severe anxiety and nasty hornet stings. As if that’s not bad enough, Charlie fails hard when attempting to describe himself as a “philanthropist.” He’s essentially a hot mess, and each spoken word doesn’t help matters either. But like a true gentleman, Charlie ultimately reveals the truth, thus making his sweaty appearance and poor communication skills just a little bit less offensive.

#4: The Sty
“Sex and the City” (1998-2004)


In a poignant Season 6 episode about personal and professional investments, Carrie Bradshaw decides to “simu-date.” Not only does she have a meeting with Jack Berger, but she also makes time for Mr. Willie Applegate, a nervous graphic designer that rambles on about a sty. His anxiety doesn’t quite suit Carrie’s confident demeanor, and the poor guy only gets more rattled when birds land atop his head. He slips, he slides, and it’s an all-out fail that leads to an easy investment choice for Miss Bradshaw.

#3: Stew for Two
“30 Rock” (2006-13)


When Liz Lemon accidentally schedules a date on Valentine’s Day, she doesn’t waste any time with personal revelations. In fact, she immediately exposes her breast to Dr. Drew Baird, which is just the first of many setbacks for the potential couple. Liz also gets caught on the toilet, while Drew’s past comes up, literally, when his ex-wife makes an unexpected cameo. Both Liz and Drew mostly keep it together, however, even if their first date is neither romantic nor well thought out. But in the world of “30 Rock,” it’s just another day for Liz, cringeworthy as it may be. In fact, one could argue that it goes better than her date with Steven Black.

#2: Rachel & Steve
“Friends” (1994-2004)


In Season 1, Phoebe introduces Monica to troubled restaurant owner named Steve, and it does not go well. So, when Phoebe needed a way to drive Rachel back to Ross, she set up her friend with the same unconfident stoner. Rachel plays it cool, but Steve reveals just a bit too much about his past drug use and infertility. In fact, he doesn’t seem interested in love at all, as he’s more of the self-loathing kind of guy. But despite all the negativity and cringeworthy banter, it’s still a relative success from Phoebe’s perspective, even if Rachel didn’t know it at the time.

#1: For F**k’s Sake
“The Office” (2001-03)


In the series finale, the always-entertaining David Brent lines up a few dates – four, to be exact. After two failed engagements, he still seems hopeful; just a man excited for what could be. Within seconds, however, positivity turns to negativity as David lays eyes on his blind date and her large, white chiffon scarf. It’s not the reaction that a woman expects, but it’s certainly a classic David Brent moment, given his verbal reaction and non-verbal behavior. Whereas some television shows feature screwball comedy and over-the-top antics, this cringeworthy scene is straight to the point and paved the way for a classic Michael Scott moment in the American installment.

So, do you agree with our selections? What TV date scene makes you cringe the most? For more dramatic Top 10s published daily, be sure to subscribe to MsMojo.

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