Dating in 2025, According to Olivia Dean, Sabrina Carpenter, Amber Mark

Amber Mark wasn’t dreading going on another first date — she just hadn’t expected she would ever need to again. Her last one had gone so well that she ended up in a six-year relationship with someone who became her best friend. When it ended, due to distance and lifestyle changes, Mark remained on good enough terms with her ex that they could talk about what it would be like to put themselves out there again. But the idea of reentering the dating arena turned out to be more appealing than the reality. Mark left the date in tears. 

“It was just so sad to me. I was immediately comparing them to that person that I was in a relationship with,” the singer-songwriter tells Rolling Stone. Mark would wake up and indulge in sadness for a while, wallowing in Chet Baker’s “I Get Along Without You Very Well (Except Sometimes)” and Randy Crawford’s “Everything Must Change.” She also found comfort in a more modern heartbreak connoisseur, Sabrina Carpenter. 

“We’ve known each other for years,” says Mark, who opened for Carpenter on the Short n’ Sweet tour this fall alongside Olivia Dean. “Her and I have had these experiences with boys for so long, and we’ve spoken about it so many times.” Her consistent go-to’s were “Opposite,” from Emails I Can’t Send, and “Sharpest Tool,” from Short n’ Sweet, songs that ache with second-guessing and distorted illusions. They mirror the experiences that Mark wrote into her latest album, Pretty Idea, about loving, losing, and trying again. The record is at once sensual, self-destructive, and lovelorn. It’s an essential entry in the 2025 Pop-Girl Guide to Dating.

This year, women in pop have chronicled the chaos and confusion of dating with class, confidence, and slick humor — even when they’re only laughing to keep from crying. While Mark reassessed the scene after six years, Carpenter shared dispatches from hell (where the bar for potential suitors has been set) on Man’s Best Friend; Dean taught a masterclass in love with sharp, almost anthropological observations on The Art of Loving; and Jae Stephens kept her standards high on Total Sellout. 

The characters and circumstances that inspired each album are different, but they’re connected in their self-assurance and resilience in a precarious dating scene. Carpenter offers a precise summary on “When Did You Get Hot?” Ready to put herself out there again — after her simple request on “Please Please Please” (“I beg you, don’t embarrass me, motherfucker”) went ignored — she announces, “Now, I’m at the prospect convention.” The lyric calls to mind the image of a flea market. There might be some killer, one-of-a-kind pieces hidden in there somewhere. But is it worth digging through all of the junk to find them? 

“The state of dating these days, it’s not ideal,” Mark says. That’s putting it nicely. A recent year-end report from Hinge found that 52 percent of daters feel “ashamed after being emotionally vulnerable,” while 58 percent of Gen Z men are turning to AI to help start conversations on the app compared to 40 percent of women. Last November, Bumble published a report on dating trends and forecasted that 2025 would be “a transitional year, with women very clear about what they want and need, and what they are no longer willing to tolerate when it comes to dating and relationships.” This particular set of pop releases puts this prediction into practice.

“I give up on love too fast, so my therapist says,” Stephens sings on “Choosy,” a synth-packed song about her one-strike-and-you’re-out approach to dating. “I wasn’t writing that song with plans to break up with my boyfriend,” she tells Rolling Stone. “I think deep down I knew that I wanted to, and then a week later, it fucking happened.” The mourning period was almost nonexistent — she’s been told before that she “writes about men like they’re disposable.” Nonessential is maybe a more apt term. “Boys are like buses,” she says, echoing a lyric from “Boyfriend Forever.” “Give it five minutes. Another one will roll through, and then I’ll go through the vetting process again if I feel like it.” 

It’s a needed reminder at a time when women often question their self-worth based on app algorithms that have given men a false illusion of access, or turn their most disastrous dates into story-time content on TikTok. In both directions, dating has been overhauled in a way that increasingly discards compassion and empathy. Dean was thinking about this while making The Art of Loving, a record she hopes makes listeners “think about love, where it exists in your life, and how you treat other people,” she told Elle. It’s also about how you treat yourself. Dean already knows the answer when she asks “Is it thinking too high of myself to not wanna be sad?” on “Something Inbetween.”

Dating should be well-intentioned and softhearted, the record emphasizes, and it should never come as a threat to your guiding principles. Listening to Mark, 31, Stephens, 27, Dean, 26, and Carpenter, 25, it’s obvious that they’re true lover girls at heart — they just don’t believe every fairy tale they’ve been sold about love. They’ve encountered their fair share of mixed signals, commitment issues, and relationships that crumble without the foundation of friendship, or at the very least, care. They’ve advised their friends about the same romantic problems, and the women in their audience have found comfort in their shared experiences. 

Settling for less is out of the question. Dean emphasizes this with undeniable charm on “So Easy (To Fall in Love),” a record that acknowledges how lucky anyone would be to love and be loved by her. Carpenter takes second-chance romance off the table on “Goodbye,” but only after circling back on “We Almost Broke Up Again Last Night.” Stephens keeps her options open on “SMH,” while Mark encourages her date to make a move before he misses his chance on “OOO.” Their self-assurance and personal growth builds a strong case for leaving situationships in 2025. 

“Love and heartbreak, it’s been sung about many, many, many times,” Mark says, “and it’s always beautiful to see how we can take something that is so core to who we are as human beings and make it our own.” At the end of Pretty Idea, she asks a guiding question: “Were you just a lesson in love and rejection?” Mark still isn’t sure, but it helped to share her stories on the same stage as Dean and Carpenter, something she says she’ll always hold close to her heart. “Sabrina, she really is very blunt about how hellish it can be to date, and I definitely feel her on that,” she says. “Olivia has very calm energy to me, and so she always has this very beautifully calm approach to expressing that same feeling.” 

On “My Man on Willpower,” Carpenter deploys her signature satire to describe the “fucked-up romantic dark comedy” she’s living in across Man’s Best Friend. It gets so bad, she reveals on “Tears,” that competence in a man starts to seem like an aphrodisiac. “Women have to reshape their dialogue and overall intentions in order to make sure they’re not coming off a certain way,” Carpenter told Rolling Stone earlier this year about leaning on sarcasm to communicate hard, often intensely self-aware truths. “When in reality, I’ve started to realize it doesn’t make you a bad person to be assertive, or know what you want.” 

When Dean sings “I don’t want a boyfriend” on “Nice to Each Other,” it’s not delivered with any kind of callousness, just a sense of certainty. Even after taking the chance for a relationship off the table, she still leads with lighthearted flirtation. “I think people have found a lot of liberation in that,” Dean said. “It’s almost kind of rebellious. I think as women, we are really conditioned to think that’s something you should start looking for, planning towards, and investing a lot of time and energy into.” On the album, she shares the heartening sentiment that “love is never wasted when it’s shared,” but overall, there are some definite diminishing returns.

In November, British Vogue published an essay titled Is Having a Boyfriend Embarrassing Now? The article interrogated the idea that some women have become reluctant to publicly showcase their partners online for fear of coming across as a boyfriend-obsessed loser. At the same time, it continues, single women are reveling in the freedom of not being bound to traditional dating expectations. The author, Chanté Joseph, unintentionally set a discourse fire that raged for days. It was fueled, at least partially, by reactionary takes from people who hadn’t read beyond the headline. On the other side was an authentic assessment of the state of dating that is becoming hard to ignore. 

“People were tagging me, like, ‘Did you write this?’” Stephens says. “I was like, ‘What? I would never!’ Then I read it, and I was like, ‘Is this fucking play about me?’” She adds, “Who you’re dating should be the least interesting thing about you.” Stephens has dated men who were insecure about never appearing on her social media, which she reserves for promoting her music and capturing her personality. They didn’t last long. “[Dating] is supposed to be truthful to you,” she says. “Realistically, my truth was not accepted by this person. That’s OK. They’re not wrong for that. They just probably shouldn’t date a pop star.” 

In a follow-up essay, Joseph reported receiving “hateful abuse,” mostly from men, in response to her viral article. “They likely saw the article as a threat to a system that has historically favored them,” she wrote. “If having a man used to be the ultimate prize, and now some women are questioning whether it is anymore, well … that’s bound to be destabilizing.” Stephens hasn’t dated any men she believes are bad people, per se — they were just kind of annoying. “I appreciate delivering that with a wink and a smile,” she says. “I’m always going to choose me and my needs over somebody who doesn’t appear to care about my needs at all.” 

They’ve gotten pretty good at redirecting negative emotions before they can internalize them too deeply. “Whatever is meant for me is meant for me, and I’m happy to put that out there,” Stephens says. “Because I do think that it will inform the listener and give them a different perspective.” Words of affirmation as a love language shouldn’t only be reserved for relationships. They can inspire self-certainty, too. “Each night, I found my light in the mirror/Stars shine in my eyes,” Mark sings on “Doin’ Me.” It pairs well with Dean’s persistent reassurance on “Baby Steps,” where she notes “I’ll be my own pair of safe hands” and “There’ll be roses on the shelf, ’cause this house gon’ love itself.” 

As 2025 comes to an end, Stephens is saying goodbye to uncertainty and second-guessing. “Leave the overthinking behind and bring the intuition and the gut [feeling] back,” she says. Mark is over it, too, and will be ditching having anxiety around dating in the new year. Between these four records, there’s no shortage of reminders that exploring new sparks should be fun and flirty — from Carpenter’s “House Tour” and Dean’s “Man I Need” to Mark’s “Let Me Love You” and Stephens’ “Afterbody.” When butterflies become indistinguishable from a panic attack, it’s time to go.

These records cover some hefty emotional ground as it contends with relationships and experiences that can impact self-perception so deeply. But they also make a strong case for self-preservation and confidence without complete cynicism. Love is all around. There’s no need to settle for something that only slightly resembles it.

“I think we inherently just love magic, and that goes hand in hand with the idea of falling in love, and the actual feeling of falling in love,” Mark says. “You can find that in anything and anyone. I imagine it is something very sparkly, illuminating, and bioluminescent in our souls. That’s what keeps us going and keeps the hope there.”