16 Celebrity Dates Gone Wrong: These Celebrities Reveal Their Worst Dates Ever

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Dating mishaps aren’t reserved for the average person; celebrities, with their larger-than-life personas, find themselves in awkward, surprising, or downright bizarre dating scenarios just like the rest of us. These stories serve as a reminder that beneath the glamour, celebrities are human too, susceptible to the unpredictable nature of dating.

From unexpected nosebleeds to dates who reveal their true colors in shocking ways, these anecdotes highlight that the search for connection can lead to memorable stories, not all of which have fairy-tale endings. Whether it’s a misjudged movie choice or a misplaced comment about appearance, it’s clear that dating is an art filled with potential missteps, regardless of one’s status.

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Ariana Grande

Ariana Grande shared a memorable date mishap with CelebsNow, where a romantic moment led to an unexpected nosebleed. The situation escalated when they returned to his car to address the bleeding, just as her friends passed by and misinterpreted the scene, fearing for her safety. Grande humorously noted this as one of her more unusual dating experiences, thankfully without recent repeats of such incidents.

Tori Spelling

Tori Spelling once went on a date with Eddie Cibrian, where she ended up too intoxicated after agreeing to just drinks instead of dinner. Her nervousness led her to vomit in the restaurant’s kitchen. Later, she discovered Cibrian’s interest was more in gaining an audition through her connections than in her personally.

Amy Schumer

Amy Schumer recounted a humorous misunderstanding on a date during her appearance on ‘Live with Kelly and Michael’. When asked whom she would choose to have lunch with, living or dead, Schumer chose Mark Twain. Her date’s response was a perplexed, “No, it has to be somebody real,” revealing a surprising gap in his knowledge. This amusing anecdote underscores the unpredictability and potential for unexpected moments in dating.

Ed Sheeran

Ed Sheeran shared with Cosmopolitan a painful dating experience that inspired one of his songs from the album “X.” He recounted how a girl he was dating slept with his friend at his own party while they were staying in the same hotel. Additionally, Sheeran described to Graham Norton another unusual date where he brought a Lego set, assembled it, and then simply left, showcasing his unique approach to dealing with less-than-ideal date scenarios.

Tina Fey

During her college years, Tina Fey experienced a less-than-ideal date, as she shared with indieLondon. Her date told her she could be “really pretty” if she lost some weight, making this remark while they were on the date itself. This story highlights the unfortunate reality of unsolicited opinions and unrealistic beauty standards even in supposedly romantic settings.

Emma Watson

Emma Watson recounted a particularly disappointing date to The Telegraph, where her date expressed an inability to be friends with anyone he found unattractive or overweight. Watson quickly realized his problematic views and described him as “a nutter,” indicating a swift end to any potential connection between them. This experience highlights the importance of shared values and respect in potential partners.

Awkwafina

Awkwafina’s bad date involved a man who ordered a single well-done steak for them to share, which he then cut into tiny pieces. She felt he displayed controlling behavior throughout the evening, leading her to question her own feelings and ultimately decide against seeing him again.

Charlize Theron

Charlize Theron’s date started well but took a turn when her date kissed her goodnight. The moment was ruined when he opened his eyes during the kiss, a move that Theron found unsettling and off-putting, making a potentially romantic moment awkward.

Mindy Kaling

Mindy Kaling went on a date that turned out not to be a date at all. She was excited and attracted to the guy, but during the outing, it became clear he viewed the dinner as purely platonic. He even discussed another actress he was interested in dating and, in the end, they split the check, highlighting the miscommunication and Kaling’s disappointment.

Kelly Clarkson

Kelly Clarkson once escaped a date at Bennigan’s by leaving through the bathroom. The date was going poorly, largely due to the man’s fixation on their slight height difference. Clarkson’s decision to leave reflects her desire for a genuine connection over superficial concerns.

Jameela Jamil

Jameela Jamil shared a shocking date story on “Today,” where what started as her first booty call ended in disaster. Upon entering her apartment, the man collapsed, breaking his front teeth and splitting his chin open due to the misuse of a drug intended to enhance sexual performance. The incident resulted in his teeth scattering across her apartment, turning what was supposed to be an intimate encounter into an emergency situation.

Christina Milian

Christina Milian had a challenging dating experience with someone who had persistently bad breath. Despite attempts to improve the situation, including the use of gum, the issue persisted, affecting their time together in enclosed spaces like elevators and cars.

Camila Cabello

Camila Cabello recounted a date where her companion chose not to reveal the movie they were watching in advance, leading to a surprise viewing of “Ouija Board.” She speculated he thought the horror film would be a cute opportunity to get closer as she became scared. However, the theater’s cozy setup with lay-down seats and blankets allowed her to hide under the blanket for the entirety of the movie, thwarting any chance for the intended closeness.

Justin Bieber

Justin Bieber had an awkward date experience at King’s Buffet, where he decided to eat spaghetti and meatballs—a choice he later regretted. The meal ended up all over him, leading to an embarrassing moment. This incident was significant enough that the girl chose not to go out with him again.

Loni Love

Loni Love experienced a unique mishap on a boat ride date when a gust of wind unexpectedly blew off her wig. Fortunately, the wig was found resting on a post, allowing them to retrieve it. This incident adds a humorous twist to the challenges of dating, showcasing the importance of being prepared for the unexpected.

Melissa McCarthy

Melissa McCarthy humorously recounted on Jimmy Kimmel Live a date with a man who was both frugal and awkward. He complained about the prices at a restaurant and claimed he could cook cheaper meals at home. The date took a bizarre turn when he mentioned having a peculiar item in his bag, intended as a sexual accessory, which he oddly acquired from a coworker. This unexpected and inappropriate offer, especially after a disappointing date, left McCarthy with a memorable story.

How To Deal With A Bad Date

Dealing with a date that’s going wrong requires tact and can vary based on the level of discomfort:

• Mild Awkwardness: Try to steer the conversation to common interests or lighter topics. Sometimes, a change in subject can alleviate tension.
• Moderate Discomfort: Suggest moving to a different location or activity. Sometimes, a change of scenery can reset the mood and improve the date.
• Significant Issues: If you feel unsafe or extremely uncomfortable, it’s okay to end the date early. Politely explain that you need to leave and ensure your safety.
• Overall Strategy: Always listen to your instincts. If something doesn’t feel right, it’s better to address it directly or leave the situation if necessary.

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