That love, however, has been a problem for Colton on his season of The Bachelor, as Wells noted while speaking with ET's Lauren Zima for Roses and Rose Live on Tuesday.
"I think you need to keep your cards close to your chest for this exact reason," he said of women like Caelynn and Hannah G. being incredibly blindsided by their breakups. "He really hurt a lot of people, which is tough, but the irony is that he's the one who ended up getting hurt."
"Not a smart play," Wells added.
Fans have watched Colton tell several women over the course of the season that he's "falling in love" with them, and on last week's episode, he told Cassie that he was officially "in love" with her -- even though she didn't reciprocate his feelings. She told him that she wasn't sure if she could ever get there with him and said goodbye... prompting him to jump over a fence and break up with the remaining two women, Hannah G. and Tayshia.
Cassie's dad, Matt Randolph, seemed to have been the deciding factor in Cassie breaking things off with Colton, as he was the only man to not give Colton his blessing to get engaged during hometown dates. Matt also showed up in Portugal to warn his daughter that he didn't think she was ready to get engaged.
It's this reason that Wells isn't exactly sure if things will work out when Colton tries to reconcile with Cassie -- despite the Bachelor telling Chris Harrison that he's sure Cassie's in love with him, even if she won't say it.
"One of her big apprehensions was her family," Wells noted. "I bet her dad feels kind of like a jerk right now, because he sabotaged it the first time, [saying] 'I don't give you my blessing.' And then he flies to Portugal to be like, 'Maybe you shouldn't do this.' And now this poor kid on national TV is baring his soul, jumping over fences, and now leaving the show for his daughter."
"I really do hope that if there is a way back for [Colton and Cassie], that the father got to see all that and is like, 'I really misread the situation,'" he said.
While we'll have to wait to find out how things end with the pair, Wells is a huge fan of Colton's big finale so far.
"This is the most romantic Bachelor. He's obviously doing the thing they didn't want him to do. He didn't do two fantasy suites. He's dumping girls, he's leaving the show for [Cassie]. It's crazy stuff that he's doing, and I actually commend him," he shared.
"He's doing the right thing," Wells insisted. "He found the person he wants to spend the rest of his life with; it's just not going the right way."
Colton's journey will continue with night two of the Bachelor finale on Tuesday, airing at 8 p.m. ET/PT on ABC. Join ET's Bachelor Nation Facebook group here, and tune in to ET Live for Zima's take on Colton's big ending at 7 p.m. ET!