Lana Del Rey's Relationship History

Lana Del Rey mostly keeps her relationships out of the public eye despite her mostly romance-focused song lyrics. If you're a fan of the songstress, you probably know that her music spares few details when it comes to exploring the topic of love. You may have even wondered how much of her real-life love life inspires her lyrics.

Del Rey spoke on this topic herself during an interview with Complex in 2014. She explained the meaning behind her song "F**ked My Way Up To The Top" and how it speaks to her experience dating in Hollywood. "It's commentary, like, 'I know what you think of me,' and I'm alluding to that," the "Video Games" singer said. "You know, I have slept with a lot of guys in the industry, but none of them helped me get my record deals. Which is annoying."

Del Rey was also asked about the worst dating advice she's ever received. "That love doesn't come easily and that relationships are supposed to be a struggle," the star responded. "Everything else is so hard; hopefully love is the one thing that is actually fun." While the "A&W" singer doesn't seem to be a fan of struggle love, her relationship history suggests it isn't foreign to her.

Keep reading to find out all about Lana Del Rey's former flings.

Lana Del Rey began dating Scottish musician Barrie-James O'Neill of rock band Kassidy in 2011. Outlets speculated that the couple went on to get engaged in 2014 after Del Rey was seen sporting a giant diamond on her ring finger. If the musicians were ever engaged, it didn't last very long because they parted ways just months later. Del Rey broke the news in an interview with Switzerland's 20 Minuten newspaper. "We are currently not together." she shared, according to an English translation from Daily Mail. "He is a wonderful person. But there are some things with which he has to deal. I will not explain it in detail. This was hard on our relationship, I no longer felt free. We'll see how it goes."

It turns out that fans weren't the only ones who found out about the split via the media, O'Neill claimed he had no idea he and Del Rey were no longer together until he read the news online — Yikes! He explained he received a phone call from a family member about the split. "I was like 'That's news to me — where did you hear that?' And it was on this website," the musician told The Scottish Sun (via NME). "I'm thinking it's a load of s**t and gossip. But it wasn't. That's how I found out." O'Neill went on to share he believed Del Rey didn't have the guts to tell him in person.

Lana Del Rey's relationship with Francesco Carrozzini was arguably one of her most public. She and the high-profile fashion photographer and director were often photographed together during outings, and they weren't afraid to pack on the PDA. In fact, the couple was spotted on a romantic vacation in Portofino, Italy a week after Del Rey announced her breakup with Barrie-James O'Neill to both the world and O'Neill himself in an interview. 

The new couple was also reportedly seen attending a friend's wedding. It probably wasn't easy for the musician to find out his ex had moved on so quickly, but Del Rey seemed to be really enjoying the new relationship ... at first.

Photos suggested that Del Rey and Carrozzini had a fairytale romance, but like most relationships, the pair had their ups and downs. According to New York Daily News' Confidential, an "eyewitness" saw the couple arguing at Los Angeles International Airport (LAX). "They were fighting at the Delta terminal at LAX Airport on Monday," they alleged in a January 2015 article. "Lana was completely in tears, crying her eyes out, and fighting with her boyfriend. They looked like they were having a big blow-up fight. Lana looked completely stressed out and upset." There could have been some truth to this claim because Del Rey and Carrozzini reportedly broke up in November 2015.

G-Easy and Lana Del Rey caused quite a stir after the world found out about their relationship through a witness who allegedly saw them getting cozy at the Coachella music festival in 2017. "They were together for the entire weekend," the unnamed source told Mirror. "They barely left one ­another's sides and looked very lovey-dovey. They were kissing and whispering in each other's ears." They also claimed the pair didn't attend the festival alone and were accompanied by a group of friends. The alleged witness added, "She was dancing the whole time during Kendrick's ­performance and he was ­actually watching her more than the stage."

The couple's honeymoon phase may have not lasted long because they reportedly parted ways in 2017. The breakup wasn't friendly. Lana Del Rey seemingly dissed G-Easy while performing her single "White Mustang." Fans believe the song is about the rapper, and Del Rey may have confirmed this when she changed the song's lyrics on stage that night. The original lyrics read, "Couldn't stop the way I was feeling the day your record dropped," but the musician sang "his record" instead. She followed that up with "And it wasn't even that good!" G-Easy appeared to respond to his ex's diss in his song "Moana." The lyrics read, "I know a Keisha and I know Lana, they try to get me back, but I'm like, "No, nah, nah." The rapper also penned, "I'm sorry, I don't want no drama, nah, that's a hard no, pass."

Lana Del Rey broke her pattern of dating men in the entertainment industry when she began seeing police officer Sean Larkin in 2019. The couple attended the 2020 Grammys together after Del Rey confirmed their relationship during an interview with Los Angeles Times. The star spoke about being photographed with Larkin during a Central Park outing in New York. "I didn't know we were being photographed," she replied. "I would've worn something different."

The "Summertime Sadness" singer was then asked if the photos caught her off guard. "Yeah," she admitted. "It's funny because I was with someone for years and we never had that problem." Del Rey also spoke about the potential controversy surrounding dating a police officer. "Well, the thing is, he's a good cop," she said in the interview. "He gets it. He sees both sides of things." Still, some fans were upset with Del Rey's taste in men. One Twitter user wrote, "lana del rey dating a cop? hate to see that."

Those upset fans may have been happy to hear that Del Rey and Larkin became "just friends" as of March 2020, according to an interview Larkin did for The New York Times. The Tulsa, Oklahoma police officer also shared details about his seemingly very tame relationship with the musician in that interview. "We all Super Bowl partied together, dinners and things like that," Larkin said in part. "Normal things couples do with their friends."

Fans speculated that Lana Del Rey was engaged to her musician boyfriend Clayton Johnson after she was seen sporting a large diamond ring in December 2020. An unnamed source reportedly "confirmed" the engagement, according to People. They also alleged the couple met via a dating app. The pair confirmed their relationship with a now-deleted mirror selfie Del Rey snapped while planting a kiss on Johnson.

The couple enjoyed cozy getaways at Johnson's family's farm in Modesto, California, as Del Rey revealed in an interview with Mojo Magazine (via People). "I'm at his parents' farm, so we're in, like, the guest house," the singer told the outlet. "It's pretty idyllic: Northern California, pretty cold, 40 degrees and a little fireplace." 

It seems that the star got along well with Johnson's family, because she shared, "We had a sweet little night singing all the old Disney and holiday songs — not what I expected after a long car ride, but everyone was in a good mood," In October 2021, reports alleged the pair broke up. "She's been working on the new album," an unnamed "source" told Mirror. "Lockdown had its struggles and they have sadly gone their separate ways."

Lana Del Rey and fellow musician Jack Donoghue occasionally documented their relationship on social media but were otherwise very private. Del Rey first revealed she'd been spending time with Donoghue when she took to Instagram to post (and delete) a video with the producer at a monster truck race. Del Rey was also in attendance at her then-beau's birthday party in 2022.

The duo made their relationship Instagram official when they posed in front of Chicago's Cook County Jail in July 2022. Donoghue posted the set of pics to his Instagram account and captioned the post, "family visit." Definitely not the most romantic couple's photo. These since-deleted pics were pretty much the only time the pair ever gave fans a peek into their relationship.

We may have received more information about the couple from an anonymous source who spoke to Daily Mail. "They seem really into each other," they claimed. "I mean, she's made pretty clear in her music she likes bad boys with tattoos, Jack is that to the Nth level. Jack is all dark and edgy and seems anti-everything but underneath all that he's actually a good-looking guy, an all-American hunk. He's kind of like this troubled, hot guy, someone who maybe played football in high school but then dropped out to chase his demons." Well, it looks like Donoghue was Del Rey's type.

Fans never got a formal confirmation that Jack Donoghue and Lana Del Rey broke up, so they were probably shocked to find out that the "13 Beaches" singer got engaged to music manager Evan Winiker in March 2023. The couple was reportedly spotted at a chili cook-off in Malibu and at a restaurant in California on a separate occasion.

It might be safe to say that Evan Winiker has a very successful career in the entertainment industry because he reportedly dropped $300,000 on Del Rey's engagement ring. The songstress was seen sporting the pricey ring at Billboard's 2023 Women in Music Ceremony. Engagement ring specialist Jessica Flinn-Allen spoke to The Richest about the details of the stunning diamond Del Rey revealed at the event. "The engagement ring is a traditional and timeless setting style, a three-stone ring in white metal, most likely platinum," she explained. "The ring features a large, round diamond in the centre, flanked by two smaller round-cut diamonds on either side, creating a symmetrical and elegant design."

Now let's dig into how Winiker is able to afford such an impressive ring. He is a managing partner at Range Media where he works with a number of artists like Daya, Disco Biscuits, Skyler, and more. He was previously a member of rock band Steel Train. Del Rey's longtime music producer Jack Antonoff was also a member of the band, so perhaps this is how Winiker and the singer first crossed paths.