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Every Single ‘Bachelor’ and ‘Bachelorette’ Contestant Who Has Dated an Actual Celeb

Tyler Cameron is on this list twice...just saying.

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This weird thing has been happening lately: Former Bachelorette and Bachelor stars keep getting lost in Hollywood and dating outside of Bachelor Nation. Like, this year alone, Tyler Cameron has managed to date not one, but two actual A-listers. See which other Bachelor stars have dated actual celebs, ahead. Spoiler: Kris Jenner is on this list.

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Mike Johnson and Demi Lovato

Things didn’t work out between Mike Johnson and Bachelorette Hannah Brown, but he managed to find love in the unlikeliest of places: Demi Lovato’s Instagram DMs. Thanks to some extremely thirsty public flirting, Mike and Demi were summer 2019’s briefest celebrity fling.

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Mike Johnson and Demi Lovato

Behold: the Instagram Story that started it all. After Demi posted this, it didn’t take long for Mike to start commenting on her bikini pics and eventually ask her out on a date. “I’m just getting to know Demi. I think she’s absolutely fantastic and I don’t want no pressure on her, no pressure on me, we’re just trying to get to know each other. That’s all,” he told E! News. Unfortunately, our dude went on iHeart Radio’s Almost Famous podcast and said Demi “kisses really well.” She understandably ended the relationship. Can’t be dating a guy who kisses and tells!

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Tyler Cameron and Gigi Hadid

Fun fact: This summer fling also started on Instagram. Gigi and Tyler started following each other during Hannah Brown’s season of The Bachelorette. In a shocking twist, Tyler was seen leaving Gigi’s apartment just days after he was spotted leaving Hannah’s apartment.

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Tyler Cameron and Gigi Hadid

In the course of their brief relationship, Tyler and Gigi went to Lake George on a mini vacation, and she even introduced him to Serena Williams. In other words, things were super serious...until they weren’t.

In early October 2019, Us Weekly sources confirmed that “Tyler is single” and “He and Gigi Hadid are no longer together.”

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Tyler Cameron and Stassie Karanikolaou

After his split from Gigi, Tyler reportedly moved on with none other than Kylie Jenner’s BFF, Stassie Karanikolaou. These two were spotted getting super flirty at a Clippers game in late November 2019 and were also seen making out.

“Stassie and Tyler were definitely showing PDA,” a source told E! News. “They stuck by each other’s sides the entire night,” the source added. “Tyler was holding Stassie at one point and they were dancing. They were chatting the entire night, whispering in each other’s ears and Tyler grabbed Stassie’s face at one point for a kiss.”

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Wells Adams and Sarah Hyland

Sarah and Wells are one of the only Bachelor Nation x celebrity success stories on this list and, honestly, they’re pretty damn cute. Their relationship is all thanks to the wonders of social media. Basically, Sarah made it more than clear that she was horny for Wells while watching him on TV in July 2016.

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Wells Adams and Sarah Hyland

Behold: the tweets that started it all. Before long, these two were spotted hanging in the same place and doing couples’ Halloween together. They even spent Thanksgiving and Christmas 2017 with each other, so, yeah, things got serious faster than you can say “right reasons.”

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Wells Adams and Sarah Hyland

ICYMI, Sarah and Wells spent the next few years being insanely adorable on social media. Like, can we please talk about this anniversary post Wells dedicated to Sarah, where he talks about the first time they said, “I love you?”

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Wells Adams and Sarah Hyland

Flash-forward to summer ’19 when Wells surprised Sarah with a proposal while they were on vacation. Like, not even Chris Harrison could scheme a cuter engagement and he does this for a damn living.

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Nick Viall and Rachel Bilson

First of all, this is not the only time Bachelorette alum Nick Viall has been linked to a celebrity, so stay tuned! A bunch of Bachelor Nation fans think he’s currently dating Rachel Bilson thanks to—you guessed it—some super flirty Instagram comments.

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Nick Viall and Rachel Bilson

Let’s see, first we have this joke about Nick sliding into Rachel’s DMs....

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Nick Viall and Rachel Bilson

...Then there’s this one where Nick complimented Rachel on her “nice foliage,” ahem.

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Nick Viall and Rachel Bilson

...And finally, there’s this one where Nick casually complimented Rachel’s dress. There's lots of evidence, but back in September when Rachel was asked about whether or not she’s dating Nick, she replied, “I don’t want to talk about it.” Meanwhile, he cryptically told People, “I’m not really defining any relationships these days.” Now she's dating Bill Hader.

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Nick Viall and January Jones

Who would have thought these two would end up together? Answer: no one, and they didn’t. But Nick and January were rumored to be dating late 2016/early 2017 all because of a fated appearance she made on The Late Late Show with James Corden.

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Nick Viall and January Jones

During said appearance, January revealed that Nick, who she’d been crushing on, had reached out to her. “You don’t know if you like him or if he’s a scumbag—and I think that’s why I’m attracted to him, maybe?” she said. “He asked me to battle him on Lip Sync Battle. So is that, like, his way of asking me out, or does he have a problem with me? I don’t know what that was. But I declined, because I don’t need to be humiliated.”

A source told Page Six that Nick asked January out shortly after this clip aired, so yeah. Dude’s got game.

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Nick Viall and January Jones

But did they end up dating? Unclear. In January, January (lol) left this flirty comment on Nick’s Instagram, but in February she told Entertainment Tonight, “He’s a friend of mine. He’s super sweet. No, I’m single. But he’s a friend of mine and tells me lots of inside scoops.”

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Courtney Robertson and Jesse Metcalfe

Bachelor season 16 star Courtney Robertson dated Desperate Housewives actor Jesse Metcalfe in 2004 and dished about it in her flawlessly titled book, I Didn’t Come Here to Make Friends: Confessions of a Reality Show Villain. “I wish I could say that we were the greatest lovers since Christian Grey and Ana Steele,” Courtney wrote in perhaps the most scathing shade of all time. “But I can’t lie. The sex was pretty average. Jesse needed a lot of reassurance.” OMG.

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Courtney Robertson and Jesse Metcalfe

If you’re wondering how Jesse felt about Robertson basically accusing him of sucking at sex, he simply told Huffington Post Live, “I don’t want to help her writing career more than I already have.” He also savagely said, “I’ve dated in the past some very beautiful women that weren’t so smart, and it didn’t really keep my attention.”

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Courtney Robertson and Adrian Grenier

Jesse is far from the only celebrity Courtney spilled tea on in her book I Didn’t Come Here to Make Friends: Confessions of a Reality Show Villain. She also claimed to have met actor Adrian Grenier at an Oscars party, and said they bonded over “mutual loneliness in L.A.” More importantly, she wrote the following words that are forever etched in my brain: “He had the biggest penis I’d ever seen—and the biggest bush!”

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Courtney Robertson and Adrian Grenier

Adrian reacted to Courtney’s comment during an appearance on Watch What Happens Live and said, “I was just glad she got the size right. And she’s seen a couple of them, huh.”

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Courtney Robertson and Gerard Butler

Sorry, not done with Courtney yet. She was also deeply shady about actor Gerard Butler in I Didn’t Come Here to Make Friends: Confessions of a Reality Show Villain and called him “horny.” Direct, extremely amazing quote: “He texted me in the middle of the day. I realized I’d be giving up [a modeling fee worth $20k] to spend a few hours with a horny movie star. I went to work.”

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Courtney Robertson and Her New Man

By the way, Courtney is now in a relationship with this not-famous silver fox, so she’s definitely moved on from dating celebs.

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Ben Flajnik and...Kris Jenner

I’ll give you a moment to process because this pairing is truly weird. Momager Kris Jenner and Bachelor Ben’s alleged romance went down in 2013 when she was spotted visiting his winery with pal Jonathan Cheban.

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Ben Flajnik and Kris Jenner

See, look, Kris even posted a photo from this fated hangout sesh to Instagram. A month later, she and Ben were seen at a Kanye West concert together, so naturally the internet started assuming! Some! Things!

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Ben Flajnik and Kris Jenner

On top of all that, Kris trolled everyone with this photo of her, Ben, and a friend with the caption “date night.” So...were they dating? Probably not, considering Kris’s sister Karen allegedly told In Touch, “I texted her about Ben the Bachelor the other day and asked if they were dating. She said it was more of a business deal.” Well, okay, then.

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Colton Underwood and Aly Raisman

Colton actually dated Aly before he appeared on The Bachelorette, but, whatever, it still counts. The pair were introduced by friends during a double date and then hit up a ton of events together—including this basketball game and...

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Colton Underwood and Aly Raisman

...the freakin’ Golden Globes! All good things must come to an end though, because Colton confirmed that he and Aly had broken up in June 2017, telling the Lincoln Journal Star, “We’re taking a break right now. We’re still good friends and talk, but all that travel had been a nightmare. It ended fine. We’re in a good place.”

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Chase McNary and Tomi Lahren

After being dumped by Bachelorette star JoJo Fletcher, Chase McNary rebounded with controversial conservative host Tomi Lahren. The pair first started speculation when they showed up in this Instagram pic looking all kinds of coupled-up.

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Chase McNary and Tomi Lahren

...And let’s not forget these flirty vibes on Twitter. But, ultimately, the relationship didn’t work out. Chase told Us Weekly, “We were talking for about two weeks, but we weren’t in the same place, so we went our separate ways. I have nothing bad to say about her. She’s a great girl.”

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Ben Flajnik and Jennifer Love Hewitt

Yup, he’s back. Apparently, Ben Flajnik briefly dated ’90s icon Jennifer Love Hewitt (they chilled at his winery...much like him and Kris Jenner), but he wasn’t feeling the vibe. “It was right in the middle of the time when I was deciding to be the Bachelor,” Ben said. “When this is all said and done, ending up with a Hollywood celebrity is not something that I want.”

Right, his celeb dating history definitely shows that's the last thing he wants.

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