Caelynn kicked off Paradise by having a brief romance with Cam Ayala, whom she gave 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 everything went great.
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, 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.
Dean admitted he 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.
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.
"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 moves on with Whitney, whom he had met at Chris and Krystal's wedding in Mexico that was filmed and will air on Bachelor in Paradise.
Carbone said Connor waited for Whitney to arrive on the beach in Paradise but she never did, and so he left as a result.
"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 reported.
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 seven 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."
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.