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 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 thought their first conversation was 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 like a self-declared idiot again.
Caelynn therefore began to slowly let her walls down for Dean.
Dean admitted he lived in a van and had no job or real ambition, but Caelynn found him funny and exciting. She also considered it cool that Dean wanted to travel the world, especially since she loves to travel herself.
The pair could envision having adventures together, and so Dean earned Caelynn's rose at the second Rose Ceremony of the season.
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Once they connected, Dean became Caelynn's priority, and Dean chose to turn down potential dates with beautiful newcomers, including Jennifer Saviano.
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 and figured Dean was after the same thing, 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.
"I didn't come here to literally date another Blake," Caelynn said in a confessional.
Caelynn therefore decided to confront and challenge Dean about his motives. 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.
But Dean couldn't give her that. While Dean said Caelynn was the only woman whom he wanted to spend time with in Paradise, he admitted he sucked at dating and couldn't see himself settling down any time soon.
"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.
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 started dating Connor
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.
Dean returned right before Caelynn's "boom-boom room" night with Connor
After Caelynn gave Connor a rose at the fourth Rose Ceremony, their relationship really started to heat up and they didn't seem to spend much time apart.
Caelynn expressed relief over not ending up with Dean and living in a van with a guy with a mustache.
Just as Connor and Caelynn's romance was getting serious and the couple looked forward to taking their relationship to the next level in the "boom-boom room" that night, Dean suddenly showed up in Mexico with his mustache shaved.
Dean pulled Caelynn aside and expressed his true feelings to her, saying he regretted ever leaving in the first place.
Dean explained to Caelynn that their first date was the best date of his life given she had chosen to accept everything about himself, the flaws and all. Dean said they got closer and closer but he tried to keep her at arm's length for the sake of "self-preservation."
Dean said he decided to make a decision for Caelynn to leave Paradise, which wasn't his decision to make, and then he returned to San Diego, CA.
"The entire flight back, I literally could not stop thinking about you," Dean told her. "I rented a car and drove to the Grand Canyon, and when I was there, I thought about how badly I wished you were there with me."
Dean said he could've waited until Caelynn left Mexico to talk again but he didn't want to wait that long in order to prevent her from falling for someone else.
"Connor came down and we've been trying to explore things, and it's just easy," Caelynn said.
"Who the f-ck wants easy?" Dean asked.
Caelynn seemed to melt while listening to Dean's speech. Caelynn admitted she had something "special" and "passionate" with Dean and he challenged her -- but also scared her at the same time.
Caelynn was confused and said she wants a partner in life, but then Dean replied, "Me too."
"It's just taken me a little bit longer to realize that. But I knew that I needed to come here and tell you that I wanted us to try and be in a relationship," Dean shared.
There were things Caelynn missed about Dean so much, but she was worried to ruin everything. Caelynn could envision a future and even children with Connor, but her feelings for Dean apparently came rushing back.
"If I continue to wait until I'm perfect to be in a relationship with someone, I'll probably be alone forever," Dean told Caelynn.
Dean didn't have it all figured out, but he told Caelynn that he really wanted to be in a relationship with her after a lot of self-reflection and thought.
Dean therefore asked Caelynn if she'd leave Paradise with him that very day. She was shocked by his request and acknowledged it was a very difficult decision to make.
Did Caelynn pick Dean or Connor?
According to Reality Steve spoiler blogger Steve Carbone, Caelynn decides to pursue a relationship with Dean and leave Paradise with him as a result -- but only after a lot of "going back and forth" between her two options.
Caelynn will reportedly act torn between Dean and Connor but then she'll suddenly start making out with Dean and leave with him.
Connor and Revian's romance, however, will reportedly not last long because he had been waiting for someone special to step on the beach: Whitney Fransway from Nick Viall's The Bachelor season.
"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 a People insider, Dean "got cold feet" in Paradise and that's why he left but he realized his true feelings for Caelynn once they were apart.
"Things have been going much better between them since they left Mexico together," the insider added.
Caelynn recently told E! News her experience on the show was "horrible" and "great" at the same time.
Is Dean 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 July 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 earlier this year, 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."