Last year, Bachelor in Paradise didn't exactly go well for Dean, but will this round be any better? Um, maybe not — but at least he's more self-aware this time. On Monday's episode, Dean told Caelynn he wasn't good at dating (which, so far, seems to be true... at least, as far as anyone can tell from his reality TV relationships), but she didn't want to hear it, and it seems like this could turn into a major disaster later on.
As fans already know, Dean ended up caught in a very awkward love triangle between Danielle and Kristina that came to an explosive ending, and now, he's back — and very open about his nomadic lifestyle as he spends most of his time traveling and living in his van without staying in one place for very long. But Caelynn's connection with Dean formed very quickly and seemed very strong from the start, and they've been only hanging out with each other. But for Caelynn, is that necessarily a good thing?
She was wondering if getting into a relationship with Dean was a good idea, and when she got her answer, she still didn't listen — even though Demi was very up front with her about the fact that Dean probably wouldn't be able to give her what she was looking for.
In fact, both Wells and Demi were honest with Caelynn, telling her that she shouldn't just give Dean the benefit of the doubt by default and that she needs to have a very clear conversation with him about exactly where she stands in their relationship and where she's hoping to be with him and in general after paradise to see if they were actually on the same page or if it was just her wishful thinking.
She did take the part of their advice where they told her to have that conversation, but what followed after wasn't exactly what she hoped for. Dean was totally real with her, which is what she asked for (and what she needed). He told her that he's bad at dating — after all, he does have a whole podcast called "Help! I Suck At Dating" — and that she wouldn't want to be his girlfriend after the show. And instead of taking Dean at his word, Caelynn was really upset... and it seems like she's planning to continue spending time with him despite that.
Of course, it's not like Caelynn could just turn those feelings off, but Dean has definitely given her a heads up about where he's at. It's just up to her to do with that information what she will.
Will things work out between Caelynn and Dean? It's impossible to know this early on, but when the show comes to an end, their relationship just might have to end, too — if they're still together by then. But whatever happens between them, hopefully, Caelynn's prepared for the outcome. It's hard out there on BIP, and it already seems like she could be in for a major heartbreak.