Caelynn kicked off Paradise by briefly dating Cam Ayala, who was crazy about the girl and could envision her as his future wife. Caelynn gave Cam her rose to at the first Rose Ceremony of the season.
But when Mike Johnson arrived, Caelynn switched her focus to the handsome newcomer. The pair went out on a date and they got along well. Sparks were definitely flying, at least for Mike.
But once Dean arrived in Paradise, everything changed. Caelynn found herself immediately drawn and attracted to Dean, despite his mustache, and she found their first conversation extremely light, easy and comfortable.
Dean learned Caelynn had struggled in Paradise up to that point, especially because of her past with Blake Horstmann, so he was ready to turn things around for her and show her a good time.
Dean therefore asked Caelynn out on his first date in Paradise, and the couple hit it off.
Caelynn felt the need to guard her heart and proceed with caution given Dean's reputation of being a bit of a player, but she really liked him and Dean claimed he had no intention of ever acting that way again.
Caelynn therefore began to slowly let down her walls and fall for Dean.
Dean admitted he lived in a van and had no job or real ambition, but Caelynn just found him funny. Caelynn also thought it was cool Dean's priority was to travel the world, and he did say he'd love to have someone share adventures with him.
Dean and Caelynn seemed inseparable, and Dean continued to win Caelynn's trust.
But Demi Burnett warned Caelynn that Dean was "a heartbreaker" and she shouldn't give him all of her time and attention. Demi and Bachelor in Paradise's bartender Wells Adams said Dean had a way of making women feel special yet no woman had been able to "wrangle" Dean yet.
Caelynn wanted a serious relationship, but Demi advised her to take a step back and look at the situation objectively. Demi suggested Dean was not going to change and she needed to be careful.
Wells and Demi suggested Caelynn should "lay down the law" and ask questions to make sure Dean wasn't just going to wander out of her life once Paradise ended. Caelynn realized they had a good point.
"I didn't come here to literally date another Blake," Caelynn said in a confessional.
Caelynn decided she needed to challenge Dean. She wanted to hear him say, "Yes, I want a future with you," as well as receive reassurance that her heart was safe with him.
When Caelynn talked to Dean about his reputation and how she was a bit worried, Dean assured Caelynn that she was the only woman with whom he wanted to spend his time in Paradise.
"But I suck at dating, and it's challenging for me to see myself getting to a point where I'm like, 'Alright, I'm ready to settle down now.' I'm going to take off in my van for nine months and be as free as possible," Dean explained to Caelynn.
"I know that kind of sucks to hear. It only makes sense for you to protect your heart only because I don't want a normal life and to go to dinner parties on Saturday nights where we talk about our feelings and emotions."
Caelynn could tell Dean's mind was made up and their romance would probably stop after Paradise.
"It's basically, like, a 'convince me otherwise' situation," Dean told Caelynn. "And I think you would just be miserable as my girlfriend."
Caelynn felt stupid for giving Dean the benefit of the doubt because she could tell he wanted to run away as soon as possible and just have fun. Caelynn didn't know whether she should continue spending time with him as a result, knowing her heart would be crushed.
Caelynn didn't understand why Dean came to Paradise if he didn't want to leave in a serious relationship.
However, the pair resumed their romance and Dean ended up surprising Caelynn with a birthday cake and champagne on her birthday. He had the entire cast sing to her, and Caelynn was starting to feel like Dean saw potential for something long term with her.
But after Dean gave Caelynn a rose at the third Rose Ceremony of the season, he pulled her aside to talk, telling the cameras he didn't think he could offer her a serious relationship.
Dean dumped Caelynn in Paradise
Dean started out the conversation by saying he entered Paradise expecting to have fun. He never thought he would form such a special connection with an awesome and "absolutely amazing" human being.
"But you know my weird history with this and my caution and apprehension going into it," Dean explained.
"I know I won't be able to get where you would need me to be by the end of this. Wholeheartedly, I know I won't be able to get there."
Dean said the breakup would be "a million times harder" two weeks from that point if they decided to stay together and see Paradise through, but Caelynn didn't understand why he was doing this.
Dean didn't want Caelynn to look back on Paradise and wish she had done things differently, especially with new guys coming onto the beach.
Dean therefore thought the solution would be for him to go home and allow Caelynn to get to know other men without him lurking around and making things difficult for her.
Dean said they got along great and spent every waking moment together in Paradise, but once they returned home, the situation would be different and their lifestyles wouldn't be compatible.
"I think you deserve a guy who is 100 percent gung-ho jumping into a relationship with you... I just think you deserve someone better than me, to be completely honest," Dean said.
Caelynn was frustrated Dean was making that decision for her, but he admitted he no longer wanted to string her along and it would be best for both of them to end the relationship now.
Caelynn found Dean's decision "so aggravating," and although she cried during most of the conversation, she didn't break down into tears until Dean finally walked away from her.
The cast could tell Caelynn was "crushed," and the girls rushed to comfort her after Dean left the show.
"I thought he was my forever, but he blindsided me. I don't know what I want to do. I just want him to be here," Caelynn said after Dean's exit, before telling her girlfriends she felt "like an idiot" for falling for him and trusting him.
Caelynn later told Derek Peth that Dean breaking up with her was "a cop-out" because she didn't think Dean believed he deserved to have a good woman in his life. She thought he was afraid to act on his feelings because he knew what they had was real.
Caelynn was hurting and insisted she was done with Paradise, but then she met Connor at Chris Randone and Krystal Nielson's wedding. The pair shared a kiss that night and got along great.
Connor then joined the Bachelor in Paradise cast and asked Caelynn out on a date. Her whole attitude changed at that point because Connor was her "type" and she thought she could have a healthy relationship with him.
"I need a good guy, and hopefully that's Connor," Caelynn said.
For their date, Connor and Caelynn rolled around in some body paint to create a work of art on a giant canvas. The pair had immediate chemistry and kissed as they were covered in paint.
Caelynn said she had always been attracted to Connor, and he thought their date was a lot of fun. Connor felt their conversation was natural and simply asked Caelynn to always be honest with him going forward about her intentions and feelings.
"Dean and I would have never worked, so I'm really happy now I have something that could really be something. Plus, [Connor] has his sh-t together," Caelynn said.
What happens next in Paradise for Caelynn? Did Dean stay out of the picture?
Revian will reportedly ask Connor out on a date, but at some point before the fifth Rose Ceremony, Dean returns to Mexico and insists he wants to be with Caelynn.
Carbone says Dean will come back to Paradise and express his true feelings to Caelynn, saying he regretted ever leaving in the first place.
"Dean comes back and takes Caelynn with him. While she's with Connor (someone she told people beforehand is the one guy she came on the show for), Dean shows up, pulls her aside, Caelynn is going back and forth talking between Dean and Connor, then starts making out with Dean and leaves with him," Carbone wrote in his July 23 spoilers.
Carbone said Caelynn and Dean's exit from Paradise together will leave Connor "crushed."
Connor, however, reportedly gave finding love a second chance by waiting around for Whitney Fransway from Nick Viall's The Bachelor season to show up to Paradise.
"Connor had met Whitney at Chris and Krystal's wedding. He thought she was eventually gonna come on the show. She didn't, so Connor left," Carbone reported.
But that reportedly wasn't the end of Connor's journey to find love.
"When they finally did bring Whitney on, Connor was gone. So what happened was, they actually sent Whitney to Connor's room, and Whitney and Connor got to spend a few days in Mexico together and they are still seeing each other last I checked," Carbone wrote.
Are Caelynn and Dean still together?
After Dean and Caelynn left Paradise together, they reportedly continued their relationship in the real world and are still dating! They have yet to get engaged, however.
"Dean and Caelynn are dating," a source told E! News in mid-July.
"They are now in Venice, Italy and plan to travel around Italy together before coming back to [Los Angeles]."
The report came after an eyewitness took a photo of what appeared to be Caelynn and Dean walking down the street together in Venice and sent it to Carbone, who then posted the photo on Twitter on July 13.
Prior to their trip to Venice, the source said Dean had traveled to Spain and Caelynn ended up meeting him there, resulting in four days spent together.
Although Caelynn and Dean never confirmed they were actually in Spain together on social media, they made it pretty obvious by posting photos of their experiences around the same time on their respective Instagram accounts.
"Clearly hating my time in Spain," Caelynn captioned a picture of herself smiling in Barcelona in early July.
And the following day, Dean posted a video of himself swimming in the Embalse de Yesa.
"Driving through Spain today and came across this crazy blue lake. the color reminded me of the lakes in Patagonia," Dean wrote alongside the image.
According to insiders, Caelynn and Dean "really hit it off" in Paradise, People reported.
"But then Dean got cold feet and left," an insider told People. "He got home and realized he really had feelings for Caelynn, so went back to Paradise for a second chance."
The insider added, "Things have been going much better between them since they left Mexico together."
Caelynn recently told E! News her experience on the show was "horrible" and "great" at the same time.
Is Dean really ready for a serious relationship?
"Good luck Caelynn, because in a few months, dude will move on to someone else. It's who he is," Carbone wrote in his spoilers.
Caelynn competed on Colton's season of The Bachelor earlier this year. Although Caelynn and Colton seemed to establish a deep connection, he ended up choosing Caelynn's best friend on the show, Cassie Randolph.
Dean found fame when he appeared on Rachel Lindsay's season of The Bachelorette and made it all the way to a hometown date.
After an appearance on Bachelor in Paradise, Dean later fell for Lesley Murphy on The Bachelor Winter Games, which filmed in late 2017. Dean and Lesley, however, split around April 2018.
But as recently as eight months ago, Dean had insisted all Bachelor Nation relationships were fake and insisted he would not want to be in a relationship with another franchise alum ever again.
"None of these Bachelor relationships are real, not a single one of them," Dean told Access in January.
"Maybe you've got some marriages and some kids and those ones are real, but every one of them's fake and contrived and I'm not into that."
"Granted, there are some that are real, like those ones I guess, but boyfriend-girlfriend relationships, every single one of them is fake," Dean said.
"From a marketing side of things, if you're in a relationship, you get more good notoriety, whatever it is and it's just like, who cares? I'm not going to be in a relationship for the sake of, like, image or selling more things on Instagram, you know?" Dean ranted in his interview with Access.
"So if you wouldn't be in a relationship if all of that weren't there, you shouldn't be in a relationship to begin with. That's kind of the approach I take."
Dean elaborated, "And that's kind of why I never want to get in a Bachelor relationship again because, whether or not, there is an inkling or whisper of a possibility that the other person might be in it because they see the value in it monetarily or whatever, social status wise."