D'Amore joined the show for its second season, coming into the series fresh off of a divorce that left her with "nothing." With Carter also coming off of a high-profile split herself from Brody Jenner, the two formed an easy bond.
"Caroline's an amazing woman, she's very grounded, she's really fun. She is this Italian woman who's definitely always going to speak her mind," said Carter in a confessional on Wednesday. "I really do value her and our relationship, she's obviously a very special person."
But could they be more than friends? That's what Caroline was wondering as she talked about their "flirty" relationship.
"I feel like a lot of people can relate to the one or two girlfriends in your life that you are a bit flirty with. Kaitlynn and I are definitely like that," said D'Amore. "She's so beautiful and I love her energy, so there's a little attraction there."
Speaking with her manager later in the hour, Caroline said she definitely had "a little crush" on her new friend. "I'm a little hesitant to do anything about it, because she's like my best friend," said D'Amore, joking she could approach Kaitlynn and say, "Hey, we're best friends. I also kinda want to make out with you."
"I can't say that!" she then exclaimed. "I've only been attracted to women, I've never gone for women."
While she'd only been in relationships with men in the past, she felt that was also due, in part, to societal pressure. "I feel like it's more like the connection I feel with someone. It's not about gender for me," she added.
Caroline finally confessed her true feelings for Kaitlynn while the two attended a sobriety party thrown by Jason and Ashley Wahler.
"I think, um, I don't know. I feel like a weird awkward person right now because there's something I need to talk to you about, I need to tell you," she began. "Over the past several months of us getting super close and having such a deep connection, I think I've just ... I don't know .. I've been starting to have these feelings and ... I think I have feelings for you."
"Okay," was Carter's first reaction.
"I just wanted to be honest. I thought hiding or lying about that would be lame. It just keeps coming up," D'Amore continued, before Carter let her down easy.
"I do feel like we're so close, so I get why you would feel like that. We're so similar, we literally like share everything with each other," began Kaitlynn. "I worry, because I feel like, because we're so close and I have been in a relationship with women and we have that in common, that we have that attraction, that maybe the reason you feel like that is more situational."
"Are you just saying that because you don't have the same vibe?" asked Caroline.
"I love you so much as my friend. But you're in such a new place of being single and exploring who you are, I think it's really important to take the time to find yourself right now," Carter told her, before adding, "I love you."
In a confessional, Kaitlynn said she did care about Caroline's feelings and didn't want to hurt her. But she also didn't want to "ruin" their friendship. "I just don't wanna be giving Caroline any kind of wrong impression," she added.
After the rejection, Caroline said she hoped Kaitlynn wouldn't "get weird" after. "That would suck," she added, before Carter reassured her that they were all "good."
"The Hills: New Beginnings" airs Wednesdays on MTV.