The Most Cringeworthy Celebrity Dating App Mishaps

About half of all people who’ve ever been on a dating app know the soul-crushing disappointment of being ghosted by a guy posing shirtless at the gym or holding up a dead fish. The truth is that dating online is rough, and as 34-year-old dating app user Frannie Steinlage mused to The Atlantic, dating apps have turned people into a form of “currency.” She explained, “When you have however many people you’re actively talking to, it doesn’t even cross your mind that maybe I’m throwing something away a little soon. … And if you lose one person one day, that’s fine — you have 500 others at your disposal.”

What makes dating apps great is also the same thing that makes them hard to be a place to find a deep connection. Nonetheless, they’re a necessary evil. In 2021 — especially in the era of coronavirus where people are skittish about meeting up in crowded bars with strangers — dating apps are just the way people connect. We all have a friend who’s found their spouse on a dating app. Maybe some of us are that friend, but that’s not the majority. 

At the end of the day, we can find solace in the fact that we’re not alone. Even Raya, the preferred method of swiping for A-listers, doesn’t protect celebrities from awkward (or deeply upsetting) moments. Here are some of the most cringeworthy celebrity dating app mishaps, proving there’s a fine line between the Walk of Fame and a walk of shame.

Lizzo botched her attempt at sliding into Drake's DMs

During a 2019 appearance on “Busy Tonight,” Lizzo told host Busy Phillips (via Refinery29) that she joined Raya in hopes of matching with John Mayer. Apparently, Lucy Hale has some competition. In the meantime, as she waits to stumble across his alleged profile, the “Truth Hurts” singer has become living proof that any app is a dating app if you try hard enough. Though she admittedly has room to improve on the art of picking up people on Instagram, she can almost certainly blame it on the juice.

As Lizzo told Phillips, she once made a crucial error when she checked herself after sliding private messaging a certain rapper. “I slid into Drake’s DMs, but it was bold,” she admitted (via Just Jared). “I was drunk and I was just like, ‘Let’s just see if this motherf****er can sing. And I sent him a DM … this was a while ago. And then I unsent it, and then he followed me after that.”

Following the Drake debacle, the star seems to have mastered this particular Instagram skill set as she also shot her shot with Chris Evans. In a TikTok video, she shared the “Captain America” star’s flirty response, “No shame in a drunk DM. God knows I’ve done worse on this app.” If you remember, Evans accidentally shared a very intimate photo in 2020, which may just be one of the cringiest things to happen on any app.

Ben Affleck's alleged dating app mishap went viral

There’s no way for us to explicitly verify if Ben Affleck is on Raya (sadly, we’re still on the waiting list) but the tabloids claim that the “Justice League” star has been swiping in the wake of his split from Ana De Armas. If there’s anything more cringey than having the paparazzi catch you throwing out a life-sized cardboard cutout of your ex, it’s being caught sliding into the DMs of someone who swiped left.

According to a now-viral TikTok, author Nivine Jay claimed to have accidentally rejected the actor on Raya because she thought he was a catfish. As The Wrap puts it, Affleck was “baffled by rejection” (because who in their right mind would reject him) and decided to slide into Jay’s Instagram DMs with a video proving he was, in fact, the man behind the giant phoenix back tattoo. As far as we can tell, this didn’t spark any sort of IRL romance (and frankly, the video looks like something straight out of Cameo, so it probably isn’t even true), but it did get Jay more than 1.3 million likes.

As for the “Armageddon” star, he doesn’t seem to be very lonely after all. A month before Jay’s TikTok went viral, Affleck was spotted with ex-fiance Jennifer Lopez, sparking new romance rumors and reminding us that, at any given time, we’re all a breakup away from a “Gigli” sequel.

Busy Phillips made Noah Centineo look like Raya's biggest hypocrite

Noah Centineo is no stranger to dating apps — but that doesn’t mean he likes them. Perhaps he’s had better luck with snail mail, like his character in “To All the Boys I’ve Loved Before” suggests. Either way, in 2018, the actor revealed to ET that he “tried the gauntlet” of dating apps when he was younger, but didn’t use them anymore. He even “deactivated” his Raya account. Why? As he previously told Vulture, he wanted to “bring back proper intimacy.”

“We are from a swipe right generation, and that just comes to, ‘Oh you’re cute, let’s hook up,’ and that’s that,” he said. “Where is actual, genuine connection that comes from spending quality time with someone?”

Romantic, right? Well, the illusion was shattered mere weeks after speaking to Vulture when Busy Phillips made Centineo look like the dating world’s biggest hypocrite. According to Refinery29, they appeared together on “The Late Late Show With James Corden,” where Phillips called him out for ghosting one of her writers, who he reportedly met — you guessed it — on a dating app. According to TMZ, Centineo’s team had to run major “damage control” as they “feared the story would ruin” their client’s “boy-next-door image.” As a result, the conversation that aired is reportedly only a fraction of what actually happened, and Cordon didn’t even put the clip on YouTube.

Lucy Hale was rejected by John Mayer on Raya

Of all people, of course John Mayer — who once explained to Playboy that his private parts were “like a white supremacist” and went on record boasting about having “masturbated [himself] out of serious problems in [his] life — is on Raya. According to GQ, as of 2016, his profile was “a slideshow set to Neil Young.” Apparently, not only is he on Raya, but he’s quite the prize, too.

In a 2020 interview with Cosmopolitan, “Pretty Little Liars” star Lucy Hale tried to land a date with the singer-songwriter, whose dating history involves publicly humiliating Jessica Simpson (in the very same aforementioned Playboy interview) by bragging about how she’s “sexual napalm.” If that wasn’t bad enough, he seemingly rejected Hale. “I pressed yes for him, but I don’t think he pressed yes for me,” she said.

We’re not here to judge Hale’s taste in men, but based on Taylor Swift’s alleged not-so-glowing review, she dodged a bullet. And Hale is no longer waiting for the world to change, as it was reported in February 2021 that she was romancing “Riverdale” star Skeet Ulrich, which is probably for the best.

Luann de Lesseps' app-found boyfriend allegedly dumped her for a teenager

Sometimes dating apps really do work. After Bethenny Frankel’s traumatic divorce, the former “Real Housewives of New York” star used a dating app to find her fiance Paul Bernon. Unfortunately, her co-star, Luann de Lesseps didn’t have such luck. Instead of meeting her third husband, she was met with cringe-worthy tabloid headlines. Here’s what went down.

During a November 2020 appearance on the “Ex Appeal” podcast, de Lesseps revealed that she met a new man on a dating app. In her words, Garth Wakeford — a personal trainer who also lived in the Hamptons — seemed “too good to be true” based on his profile. When they first met for coffee IRL, and he removed his mask, the cabaret singer was completely smitten. “I said, ‘Oh, my God! He’s exactly what he looks like on the app.’ … He’s tall, he’s handsome, he looks like a Viking,” she admitted.

Unfortunately, it seems like de Lesseps’ first instinct was right — the former South African rugby player was too good to be true. According to Radar, Wakeford “dumped” de Lesseps a couple months later, then started dating a local 19-year-old college student-slash-socialite named Jacqueline Leahy. As if that wasn’t already a slap in the face, Leahy is allegedly “close family friends with” Sonja Morgan. Yikes. Friends circles should be totally off limits, Right? But as de Lesseps says, money can’t buy you class. 

Even Charlize Theron has to endure uncomfortable dating app interactions

Charlize Theron doesn’t want a husband. In the past, she told Vogue that weddings look “like a lot of work” and she “never had the dream of a white dress.” You know what else is a lot of work? Dating apps. Though Theron doesn’t want to tie the knot, she’s still trolling dating apps and enduring the same awkward experiences the rest of us wish we could bleach from our memory.

In an interview with Ellen DeGeneres, the “Bombshell” actor admitted that Chelsea Handler convinced her to try a dating app for celebrities (see: Raya), but she hated it from the start. “She’s swiping all these faces of guys in all different sorts of … different variations of no clothes,” she said, “Then, they know that you’ve just said, ‘No, I don’t like you.’ … And then you have to text them, and then the flirting starts, and it’s kind of awkward because you don’t know the person, and they’re trying to be cute, and they say weird things like, ‘What’s up, sexy?’ And it’s just awkward.”

If anything, Theron is a true testament to the fact that no woman is immune. Even if you win an Oscar, you’re still subjected to the leagues of shirtless dude bros on dating apps hurling around cringe-worthy pickup lines. It never ends.

Drew Barrymore's dating app date stood her up

As it turns out, even celebrities get ditched by their dating app suitors. Somewhere out there, there’s a man who must live his life knowing that he’s the person who stood up Drew Barrymore, a veritable national treasure. It’s unclear how someone can possibly cope with that reality, but on Barrymore’s end, living well — and putting anonymous strangers publicly on blast — is the best revenge.

In a 2021 interview with Access, Barrymore revealed that “Bridgerton,” with all its old-fashioned romance, emboldened her to get with “what the modern world is about” and join a dating app, but it does not appear to be going well. During an appearance on “The Howard Stern Show,” the actor revealed that dating apps made her feel “like a conservative parent watching Elvis. I was like, ‘These hips are gonna turn my child into the devil!'” Someone even had the audacity to stand her up, though he at least was kind enough to send a text a la the infamous “Sex in the City” Post-It.

“I was, like, getting ready and on my way out the door, and yeah, [he was] like ‘I can’t.’ It was a Berger to Carrie Bradshaw, ‘I can’t. I’m sorry. Don’t hate me,’ except for his was just ‘I can’t,'” she told Stern. “You know what, I will say this to anyone out there. Thank you. You didn’t waste my time.”

Danielle Staub attempted to expose Andy Cohen's alleged dating app habits

Since the cast of “The Real Housewives” uses dating apps, it was only a matter of time before their arbiter, Andy Cohen, tried his luck. Following his split from his Ph.D. student ex, the Bravo executive tried his luck online. In a 2018 interview with Ellen DeGeneres, Cohen revealed that he used both Tinder and a “gay dating app” that kept kicking him off because “they think I’m impersonating Andy Cohen.”

Things didn’t get cringey until Danielle Staub, the reality star at the receiving end of Teresa Giudice’s infamous “Real Housewives of New Jersey” table flip, got involved following her alleged eviction from the Bravo clubhouse. In a lengthy Instagram post, Staub claimed that she was “repeatedly [defamed]” by Cohen and left the “Real Housewives” franchise to “protect [her] young children.” Though Staub’s Instagram gripes were vague, the reality star’s tirade actually began on her podcast, “Danielle Staub, Absolutely,” where she went into embarrassing detail about Cohen’s alleged dating app habits.

“The Andy I know would hit up Grindr and go on three or four Grindr dates an evening. And these are people that are pretty reputable sources. … I don’t even want to talk about the drugs and the partying.” Unfounded claims aside, as someone who’s been engaged 21 times, who is Staub to judge how someone else finds love?

Tiffany Haddish and Common's dating app stunt got the wrong kind of buzz

Tiffany Haddish is a comedian, but she’s also a business woman. While her patented purse chicken proves she’s got some excellent possible business ideas in the pipeline, her foray into Bumble wasn’t one of them. Sure, it was probably a lucrative deal, but it also didn’t make any actual sense to anyone really paying attention.

Most fans know that Haddish has been dating rapper Common for a hot minute. The pair supposedly had their “first virtual date” on Bumble, which aired on the company’s Instagram account in April 2020. In the clip, Common claims, “We can’t be in the same place right now … it’s good to see you.” The problem was, as Page Six pointed out, that the duo had obviously been living in the same house for at least a month.

A report from Deadline (via The Grio) revealed that about two weeks prior to their so-called first date, Haddish popped into Common’s live-streamed Def Comedy Jam fundraiser and admitted the pair had been quarantining together. This led tabloids to question: were the pair completely faking their dating app romance? While it’s now clear that Common and Haddish are a legitimate couple, we’re not sure Bumble had anything to do with it.

Hannah Brown's cringeworthy 'do you know who I am?' dating app moment

Hannah Brown has arguably made terrible choices when it comes to love. First, on Season 15 of “The Bachelorette,” she chose Jed Wyatt — who clearly was only on the show to promote the fact that he could play guitar — instead of Tyler Cameron or Peter Weber. Their engagement was doomed from the start and it didn’t take long for news to surface of Wyatt’s alleged secret girlfriend. Next, Brown crashed Weber’s stint on “The Bachelor,” undoubtedly picking at old wounds for the pilot she rejected (did the windmill mean nothing?). Finally, she decided to quarantine with Cameron at the start of the coronavirus pandemic. They claimed nothing happened, but the romance rumors still made headlines.

While bouncing between her “Bachelorette” exes, it’s not surprising that the reality star struggled to find love. That’s when she turned to Raya — and much like Pilot Pete or Cameron — she was coldly rejected. In an Instagram story, Brown admitted, “I don’t know if you know this but I was the bachelorette, and I can’t get on Raya. I’ve been on the waiting list for months now … Christian Mingle, here I come.” Okay, so she wasn’t outright rejected, but being on a 100,000-person waiting list is effectively the same. You’d think winning “Dancing with the Stars” would be enough or maybe, just maybe, starring in one of the most famous dating shows in television history.

Demi Lovato is sorry, not sorry they were rejected from this dating app

When Demi Lovato was nursing a broken heart from their whirlwind breakup with former fiance Max Ehrich, you can bet that they weren’t swiping on Raya. The mega-star was actually rejected from the exclusive dating app. Apparently, two Grammy nominations, two platinum albums, four gold albums, and a leading appearance in one of the most iconic Disney Channel original movies of all time doesn’t carry enough street cred.

In Lovato’s April 2020 Harper’s Bazaar cover story, the “Dancing With the Devil” singer revealed that they originally made it past Raya’s notoriously exclusive application process but deleted their account “out of respect” once they landed a partner. When that relationship ended, they re-applied for the app but were swiftly rejected. “I was like, ‘You know what? It’s fine. I don’t need to be on this because I think I’m supposed to be alone right now,'” they said. This all begs the question: if Demi Lovato isn’t famous enough for a Raya profile, what shot do the rest of us have?

Zac Efron couldn't get a single Tinder match

It’s hard to think about who would reject Zac Efron — the Troy Bolton, the same guy who managed to turn the world’s most embarrassing red carpet moment into a meaningful conversation about safe sex. Only Efron could drop a condom at the premiere of a children’s movie and emerge without so much as a scuff on his squeaky clean image. The fact is that Efron, aside from being a crush for most Tiger Beat readers circa 2006, is just flat-out likeable. Apparently, though, this sentiment doesn’t extend to dating apps.

The star’s “Mike and Dave Need Wedding Dates” character was able to find a date through Craigslist, but Efron couldn’t even get a match on Tinder. In a 2016 interview with The Times, the actor revealed, “Amazingly, when I signed up for Tinder, nobody swiped me! They thought it was fake.”

Fortunately, Efron’s dating app luck seems to have changed. According to anonymous sources who spoke to The Sun, the “High School Musical Star” spiced up his life when he swiped right on Mel B in 2018. The pair reportedly shared “a night of passion” after meeting on a “super-exclusive dating app” (aka Raya). “It wasn’t exactly a meeting of minds,” the alleged insider claimed, adding, “Neither saw it as long-term, but there was chemistry there. Mel thought Zac had an amazing body.” If you wanna be her lover, you gotta get with a dating app.

Sharon Stone was blocked by Bumble

It’s not every day you see a Golden Globe and Primetime Emmy winner on Bumble — and that might just be because the drama just isn’t worth it. Decades after her second divorce, Sharon Stone decided to dip her toe into the virtual dating pool, but users basically revolted. In a 2019 tweet, the singer revealed she had been blocked from the platform. “I went on the @bumble dating [site] and they closed my account,” she wrote. “Some users reported that it couldn’t possibly be me! Hey @bumble, is being me exclusionary? Don’t shut me out of the hive.”

According to the BBC, Stone’s ban was short-lived. Bumble’s editorial director made one thing clear: they “definitely” did want such a high-profile member, but — as Stone later theorized to ET — some of her fellow users did not. Apparently, even celebs can’t dodge the wrath of jilted men on dating apps. “I think that I said no to a couple of people that thought that it would be a nice way to be not-so-kind back,” she revealed. “I think some people don’t like to hear, ‘No, no I don’t want to go out with you.'”

Beyond that, Stone actually admitted she was having a “nice time” on Bumble. “I’ve met a couple of nice people and I’ve actually made a couple of nice friends by doing that,” she told ET.

Bachelor alum Alexis Waters tried Bumble BFF and didn't make a single friend

Alexis Waters, who rose to fame as a Season 21 contestant on “The Bachelor,” approaches dating apps the way she approached her reality show, always with a good sense of humor. Fans might remember when she was forever dubbed Dolphin Girl after crafting the fake job title of “aspiring dolphin trainer,” which she told Nicki Swift was a cannabis-fueled joke. If donning her infamous shark costume — which may just be the worst since Katy Perry’s left shark — was a high point, the low came when Waters finally resorted to Bumble.

To be clear, “The Bachelor” did actually lead Waters to love with boyfriend Tyler Fernandez, albeit in a roundabout way. The problem was finding meaningful gal pals. That pushed Waters to join to Bumble BFF, where she never even made a single friend.

In an exclusive interview, Waters told Nicki Swift that she signed up for the app when she moved to Miami because she had “no friends.” “I would go out to clubs dead alone and I was not meeting anybody. And then I just went on Bumble BFF, but I never met up with anybody because I was scared that they were going to, like, murder me or something,” she said, adding, “I never really was on a dating app, but I just was on a best friend app. So embarrassing for my life and soul.” 

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