The deckhand and stew, respectively, quickly hit it off after they boarded The Wellington at the beginning of the charter season. It wasn't long before they were a full-fledged couple on the yacht, even telling each other, "I love you." They experienced some truly romantic moments, such as Rob surprising Jess with the news that he would join her in Bali after the charter season ended and their audible alone time in a guest cabin one night.
However, Rob and Jess also encountered some challenges, including confusion over Rob's relationship status and his continued communication with his ex earlier this charter season, his interactions with Aesha Scott, and his seemingly flirtatious behavior with one of the final charter guests of the season. Both Rob and Jess expressed at times that the other seemed disconnected and distant during the charter season.
When an opportunity to do a crossing after the charter season ended came up, Rob considered taking it instead of joining Jess in Bali like he had originally planned. This resulted in an emotional moment between the two as they prepared to disembark The Wellington in the Below Deck Med Season 5 finale, which aired on October 12.
But Rob and Jess did ultimately end up leaving the boat together as The Wellington crew said their goodbyes. In the episode, we saw them kiss on the dock before an update appeared on the screen: "Instead of doing the crossing... Rob went to Bali with Jess."
We also got to see a photo of Rob and Jess sharing a smooch during their trip to Bali. The pic also featured a beach and a sunset were in the background to make it that much more dreamy.
However, getting to that point wasn't easy, according to Jess in the Below Deck Mediterranean Season 5 After Show, which you can view, above. "Rob and I, we ended up going," Jess confirmed. "He made it to Bali after a few cold feet moments, even after the show. There were two more cold feet moments. But he went."
Rob also gave some details on the vacation during the After Show. "It was amazing. It was beautiful. Got to see a different side of Jess. We could just relax and be free in each other's space," he said. "And then back to reality where things came back, and it just didn't work out."
Jess then described what happened after the Bali trip. "Um, well, I mean, I think in total, Rob and I were together for about six months in a serious relationship and basically together every day. It was definitely a roller coaster with him," she recalled. "I've never felt that sort of affection and attention and love — and then also the polar opposite."
Unfortunately, things did not work out for Rob and Jess. "It didn't end on the best note, and we're still not in the best place," Jess shared in the After Show. "It just keeps seeming to build, my disappointment for somebody that I really, truly cared about and loved and thought that I was gonna marry and spend the rest of my life with. So, to go from that to just continually finding out things new every single day is something that's really hard for me and disappointing."
Rob said that it's been difficult to relive his relationship with Jess while watching this season of Below Deck Med. "It hurts me quite a bit, because at the end of the day, we both kind of pushed each other away, out of the relationship," he explained. "We understood each other's triggers. We understood how to hurt each other. Ultimately, at the end, we both destroyed the relationship."
Jess also got emotional while opening up about the experience of watching back her relationship with Rob this season. "The show's not helpful, watching it," she said.
Rob admitted in the After Show that he still cares about Jess today. "I'll take ownership of my actions. Like, I know that I showed up, and I ruined a lot of the relationship through my inability to trust," he shared. "When I look at it now, it's f--king sad, bro. Like, I feel, I still love her. I still really love who she is as a person. She'll always have, like, a really big part of my heart."
Rob's fellow deckhand, Alex Radcliffe, also asked him during the After Show if he and Jess would ever reconnect. "You know, the problem is we both know each other, like we both know how to hurt each other and trigger each other," Rob said in response. "If we could address that and take ownership of the fact that we both created the mess at the end of the day and not use that."
Want more Below Deck Med? New episodes air every Monday at 9/8c or catch up on the entire series through the Bravo app.
Rob and Jess will reunite, along with the rest of The Wellington crew, during a two-part Below Deck Med Season 5 reunion, which kicks off on Monday, October 19 at 9/8c.
The Daily Dish is your source for all things Bravo, from behind-the-scenes scoop to breaking news, exclusive interviews, photos, original videos, and, oh, so much more. Subscribe to The Daily Dish podcast, join our Facebook group, and follow us on Instagram for the latest news hot off the presses. Sign up to become a Bravo Insider and be the first to get exclusive extras.