Lana Del Rey's Dating History: From Barrie-James O'Neill to Evan Winiker

Inside Lana Del Rey's dating history: The Grammy-winning singer is reportedly engaged to Evan Winiker. Complete story here!

Known for her scintillating public image and music, perpetually reflecting on lost love and nostalgia, Lana Del Rey is one of the most-beloved songstresses of the generation. Aside from her subtly yearning songs and her cinematic depiction of romance, Del Rey is also deemed to be the inventor or the avant-garde of the trending sad girl era. There's not an ounce of doubt that the songstress, with the most soulful, yet despondent gaze, has created and continues to make the most relatable love songs, but how much do we know about Lana's real experience in love? 

Lana's impeccable eyeliner, the cigarette between her finger, and her tragic, but cool persona were realized when she took up the seductive stage name. She was born Elizabeth Woolridge Grant and had a brief, but flop career under her birth name. Born on June 21, 1985, in New York City, she had an album released under the name, Lizzy Grant, in 2009, but it went down without a trace. Lana's viral track, Video Games, propelled her to fame in 2011.  

Inside Lana Del Rey's Dating History!   

Lana mostly keeps her love life under wraps and the only window- her music, to gain a little insight into the Grammy winner's personal life insinuates that the singer has had her heart broken many times. The Video Games crooner has never been married in her life, although she has gotten exchanged with two of her boyfriends in the past. Lana's earliest known boyfriend is Scottish singer-songwriter Barrie-James O'Neill, who she began dating shortly after rising to fame, in 2011.   

Lana and O'Neil, who was a member of the band Kassidy at the time, stuck beside each other as they navigated their respective career. The pair were even engaged at a point during their three-year-long relationship. "We are currently not together," the New York-born singer revealed in June 2014. Lana added, "he is a wonderful person. But there are some things he has to deal with." Barrie later revealed that he was blind-sighted by the news of their breakup, but still owned up to his shortcomings.   

"I had saved up a bit but I felt like a burden on Lana — as she was having to take care of me. And I don't like that, I like to provide for myself," said the singer, who has since remained amicable with Lana and even worked with her in her 2021 album, Blue Banisters. The Young and Beautiful hitmaker moved on with Italian photographer Francesco Carrozzini the same year she broke up with O'Neil, but their romance fizzled out after a year of on-and-off run. A source later revealed the couple loved each other, but was not on the same page.    

Del Rey was linked with rapper G-Eazy in April 2017. Although neither party confirmed the relationship, it seemed that it was more of a summer fling than a relationship. Del Rey's next notable relationship was with Live PD analyst Sean Larkin. Del Rey joyfully confirmed their relationship after being snapped with her cop boyfriend at New York City's Central Park. During their almost year-long romance, Lana even bonded with Larkin's kids from his previous relationship.   

The couple called it quit in March 2020 and although Sean alluded to a friendly breakup, Lana's actions said otherwise. The songstress not only released her album, Did You Know That There’s a Tunnel Under Ocean Blvd, on Sean's birthday, but also arranged a billboard advertisement for the album in Sean's hometown, Tulsa. "There's only one [billboard] and it's in Tulsa," Lana wrote on a post, and in the comment, she adds, "it's personal."   

The Summertime Sadness crooner sparked whirlwind romance rumors in late 2020, which soon turned into an engagement rumor. First, the singer was linked with musician Clayton Johnson after her split from Sean. And by December, the pair were embroiled in engagement speculation after Lana was spotted with a huge diamond ring. The two went Instagram-official in early 2021 before eventually parting ways. Del Rey was last linked with musician Jack Donoghue.  

Lana Del Rey is Engaged. Again!  

Despite several failed relationships and engagements that never turned into weddings, Del Rey is not giving up on love anytime soon. The Cinnamon Girl hitmaker is reportedly engaged to Evan Winiker, a music manager and musician. But fans should take the news with a grain of salt as it appears Lana's current relationship with the music manager isn't so different from her past relationships. The twosome has allegedly gotten engaged after a few months of dating.   

The 37-year-old singer sparked the engagement rumors after she sported a sparkly rock at the Billboard Women in Music event on March 1. The allegedly engaged pair are yet to publicly announce their betrothal and have even kept their romance on the low. Winiker is several years younger than Lana, 8 years to be precise. The 29-year-old is a managing partner at Range Media and previously worked as a musician in the band Steel Train.  

Lana certainly prefers to keep her love life away from the media, but the singer previously opened up about her aspirations for an everlasting relationship. "For someone like me – and it's not a codependent thing – I just like having someone there. I've been alone, and that's fine. But I like to come home and have someone there," Lana told Harper's Bazaar. 

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