Enigmatic singer Lana Del Rey, whose real name is Elizabeth Woolridge Grant, went through an entire metamorphosis in order to become the megastar she is today. As The Guardian wrote of an early 2009 performance from the then-Lizzy Grant, her “voice was strong, but she seemed shy and spoke quietly to the audience to a smattering of applause.” Eventually, Grant disappeared without a trace, and Del Rey suddenly took center stage. “She’s putting on a show,” mused Billboard journalist Steven Horowitz. “She’s here to entertain us.”

But what exactly has been going on in Del Rey’s personal life? Well, it’s hard to say, considering she’s notoriously private. Not much is known about the starlet’s alleged dating history, but her amicable breakup from police officer boyfriend Sean “Sticks” Larkin still made headlines in March 2020. As Rolling Stone previously wrote, the “Video Games” crooner is “a mystery that 10,000 tortured think pieces have failed to solve.” However, one person who knows the answer to this puzzle is, of course, Del Rey herself. “There’s nothing anyone could ever tell me that I don’t already know,” she told the magazine. “I know everything about myself. I know why I do what I do. All of my compulsions and interests and inspirations. I’m very in sync with that.”

So, why is it that the Manhattan-born artist seems to struggle romantically? There’s more here than what meets the eye, so we’ve rounded up the real reasons Lana Del Rey has trouble with relationships.

Does Lana Del Rey glamorize sadness?

Since her debut single, “Video Games,” came out in 2012, Lana Del Rey has been regularly criticized for glamorizing sadness. Is this perhaps something that’s bled into her relationships, as well? This argument is no secret, and even some celebs have joined in on the commentary, such as Kim Gordon of Sonic Youth.

“Today we have someone like Lana Del Rey, who doesn’t even know what feminism is, who believes women can do whatever they want, which, in her world, tilts toward self-destruction,” Gordon wrote in her 2015 memoir, Girl in a Band (via Consequence of Sound). “Naturally, it’s just a persona. If she really truly believes it’s beautiful when young musicians go out on a hot flame of drugs and depression, why doesn’t she just off herself?” Woah. While Gordon’s words seem a bit harsh, her criticism isn’t at all new. As Popdust writes, “Del Rey checked all the boxes. She was angry, irresponsible, violently expressive, in control of her own narrative and simultaneously devoted to the men in her life. She quickly became the face of the ‘sad girl’ stereotype.”

So, is Del Rey’s glamorization of sadness merely a character? As the singer previously told the Swedish outlet, Aftonbladet, “Well, it’s not a persona … It has made it easier for me to express a very clear aesthetic that I love.” As for this aesthetic? Del Rey added, “All things dark and beautiful.”

Lana Del Rey may have dated some toxic individuals

A vast number of Lana Del Rey’s songs have to do with dating seemingly toxic individuals. While opening up about her former relationship with ex-fiancé Barrie James O’Neilin a 2014 interview with Fashion (via the Daily Mail), she admitted, “It’s been a tenuous and tumultuous three years … He’s unwell and I’m unwell in some ways, and psychologically we’ve been through a lot together.”

Apart from that, the “Yayo” singer has remained very tight-lipped about her personal life. While speaking with Rolling Stone, Del Rey was asked about the lyrics to her song, “Ultraviolence,” where she croons, “He hit me and it felt like a kiss.” So, are the words autobiographical? “I guess I would say, like, I’m definitely drawn to people with a strong physicality,” she told the mag with a shrug, adding, “with more of a dominant personality.” In fact, during an interview with Swedish outlet, Aftonbladet, she deflected an even more direct question of whether or not she’s been in abusive relationships. “I don’t know what to say,” Del Rey mused. Hmm.

At the end of the day, it’s not like Del Rey has always had poisonous romances. In fact, her single “Video Games” is about the complete opposite. “I was blessed to find someone who made me so happy,” she told Rolling Stone of the story behind her hit. “And I just didn’t understand why true love shouldn’t be the end-all, be-all. I have everything else, you know?”

Lana Del Rey's career is at an all-time high

Perhaps Lana Del Rey’s difficulties with maintaining longterm relationships have nothing to do with any internal struggles. Simply put, maybe there’s something else that’s a priority — like her career. An A-lister for almost a decade, it looks like the Manhattan-born starlet has finally found her professional stride. Vox highlighted this point perfectly, summarizing, “In 2012, people called Lana Del Rey a fake. Now they call her one of the best pop stars of her generation,” adding that her latest record at the time, 2019’s Norman F**king Rockwell!, was received with widespread acclaim. Even Pitchfork named it the 19th best album of the 2010s.

Back in 2012, the Observer called Del Rey “a failed pop singer who got lip injections, changed her name, and now has a great backstory about living in a trailer that makes her New Jersey Chanteuse schtick as Urban Outfitters-ready as a pair of tight Levi’s.” Nevertheless, the “Born to Die” crooner pushed forward, and comparatively, critics eventually praised her for staying true to her brand.

So, with her singing career, does Del Rey even have time for a relationship? Who knows, but she’s definitely expanding in terms of her creative outlets. In 2018, the starlet announced she’d be releasing a book of poetry, and by 2020, fans were lucky to get a glimpse at some of her prose. At the end of the day, maybe Del Rey is too heavily engrossed in a relationship with her own mind.

Don't worry, it's not 'codependency,' but Lana Del Rey could still be clingy

When she does manage to maintain a relationship, it looks like Lana Del Rey doesn’t go for anything casual. In essence, it’s either all or nothing.

The “Doin’ Time” singer elaborated on the intensity of her romances to Rolling Stone in 2014. “It’s been beautiful, but it’s been confusing, because when that’s your prerogative, things don’t end in a traditional way,” she mused. “You don’t have that traditional relationship where maybe you go out with couples at night, or you do normal things. It’s more of an extension of the creative process. There’s high-impact events that happen, or big adventures, or big fallouts. So it’s inspiring, and it’s not grounding, but it’s what I need to keep going.”

Sure enough, intense relationships aren’t for everyone, but it looks like that’s the main sort of love that Del Rey is after. “For someone like me — and it’s not a codependent thing — I just like having someone there,” she told Billboard the following year. “I’ve been alone, and that’s fine. But I like to come home and have someone there.” Although she claims that she doesn’t have issues with codependency, it does kind of sound like just that, no?

Family may eventually come first for Lana Del Rey

Considering Lana Del Rey seems utterly engulfed in her music, will she ever prioritize having a family? “I hope so,” she told Rolling Stone in 2014. “I hope that’s in my future. If I don’t f**k everything up. I don’t know.”

It looks like although her outlook may not be the most positive, having children someday is definitely on her mind. “I’ve … really thought about it lately because I’ve just turned 30,” the “Dark Paradise” songstress mused when Billboard asked if she wants kids. “I’d love having daughters. But I don’t think it’d be a good idea to have kids with someone who wasn’t … on the same page. Who isn’t exactly — like me! Though maybe it’s best to have kids with someone who’s … normal.”

So, is being in a relationship with someone who’s similar to Del Rey a bad thing? The starlet seems to think so. Speaking with Billboard in 2015 about an old flame, the “Summertime Sadness” artist recalled, “The last one … was pretty bad. It wasn’t good to be in it, but it wasn’t good to be out of it, either. He was like a twin. Not a facsimile twin, but a real twin.” Hmm, we’re wondering if Del Rey is setting her bar too high. After all, she wants someone to inspire her and be there for her — yet she doesn’t want someone similar to her. That one may be tricky, Lana.

Many view Lana Del Rey as inauthentic

The biggest issue that critics seem to have with Lana Del Rey is the fact that many view her as inauthentic. As The Atlantic once put it, “It’s always been intuitive to think of Lana Del Rey as a ‘character.'” However, as the starlet herself even tweeted in 2019, “Never had a persona. Never needed one. Never will.”

That said, The Atlantic made some interesting points regarding Del Rey’s alleged lack of authenticity, such as the fact that she seemingly “[lives] in costume.” As the outlet noted, “She has a fashion shtick so well-defined that people can go as her for Halloween. She writes lyrics in a style that makes it seem like she wormholed from an early ’70s LSD cult and then tried to learn modern slang from a Rihanna song.” While her defenders may say that it doesn’t matter if she’s “artificial,” perhaps all the talk about it wards off potential suitors?

At the end of the day, Del Rey believes her naysayers may be a bit too harsh on her. “I mean, I’m happy when things aren’t bad,” the “Blue Jeans” crooner told Rolling Stone when asked if she’s ever not feeling blue. “I’m happy when things are just kind of calm. I love going to the ocean. I love driving. I love going to shows. Just being with people I really have fun with. I love the summer. I’m happy in the summer. Love hot, hot weather.”

Lana Del Rey has even dubbed herself as 'selfish'

There’s no denying that for Lana Del Rey, her music comes first. “I mean they say that I was singing before I was talking,” the A-lister told Bloodworks Live Studio in 2019, adding, “I actually read this book called Think and Grow Rich by Napoleon Hill … I’ll just always remember this line where he talks about burning every bridge except the one bridge to the thing that makes your heart the most on fire, and I was like, that’s definitely singing.”

During a 2014 interview with Rolling Stone, Del Rey made a candid confession. Speaking about her music, the Honeymoon starlet admitted, “I’m very selfish. I make everything for me, kind of. I mean, every little thing, down to the guitar and the drums. It’s just for me. I want to hear it, I want to drive to it, I want to swim in the ocean to it.” Considering she so openly admits she’s selfish with her music, perhaps she’s also selfish in relationships?

While the singer revealed to Bloodworks Live Studio that she “can be a bit of a people-pleaser,” she explained, “I am more eclectic than most of my friends, so I guess just doing whatever it is I feel like doing in any given moment,” and later added that she prefers to stick to her own “little crew.” At the end of the day, it looks like that’s precisely what suits Del Rey at this point.

Are Lana Del Rey's viewpoints outdated?

Along with receiving criticism for her “sad girl” aesthetic, Lana Del Rey has also received a lot of judgment for her stance on feminism — especially in her lyrics. In fact, even from the get-go, her first single “Video Games” was met with a mountain of objection. “I remember when ‘Video Games’ came out, people were like, ‘Oh my God, it’s so anti-feminist!'” the singer mused to The Washington Post in 2019. “‘You’re sitting and watching him play video games?’ I was like, ‘Well, I would play, too, now and then.'”

Del Rey’s seemingly blasé approach to such an important issue hasn’t helped her case, either. Speaking to Fader, she bluntly revealed, “For me, the issue of feminism is just not an interesting concept … Whenever people bring up feminism, I’m like, god. I’m just not really that interested.” Uh-oh. Considering many men are embracing feminist ideals in this day and age, perhaps Del Rey’s viewpoints seem a bit antiquated.

Nevertheless, Del Rey has always remained true to who she is — and unapologetically, at that. Plus, it looks like by the time her 2019 album, Norman F**king Rockwell!, was released, some of her naysayers had been silenced. As for reading any other meanings behind her songs? As Del Rey told The Washington Post, “I’m not going to tell everybody everything … There’s so much to be treasured [in a song], just keep to yourself so that nobody can trash it.”

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