Inside Lizzo's Dating History

Lizzo made headlines when she took to TikTok to reveal screenshots of her flirty Instagram DMs with "Captain America" star Chris Evans. The internet went wild over the video where Lizzo shared she had drunkenly messaged Evans. The TikTok caption warned fans "Don't drink and DM." This was not the first time the musician spoke publicly about messaging a celebrity crush. In 2019, Lizzo told Busy Philipps about a DM-and-delete incident where she attempted to flirt with Drake via Instagram. The briefly embarrassing moment worked out in her favor because the rapper followed her back. Lizzo has had a lot of luck with DM flirting, but what about the singer's dating history? Fans know the outgoing musician is relatively private about her past romances. Although it seems that Lizzo likes to keep her relationships out of the public eye, she has opened up about her dating history in the past.

Of course, she also dabbled with dating for quite a while before she became the superstar we know and love today. From falling in love to difficult breakups — it is no surprise Lizzo's dating life has inspired so many relatable hit songs.

The Grammy award-winning musician started an internet frenzy when she revealed she slid into Chris Evans' DMs. In a now-viral TikTok, Lizzo shared a screenshot of the Instagram DM she sent to Evans. The flirty message written out in emojis suggested Lizzo was attempting to shoot her shot at the actor. Fans quickly began fawning over the possibility of a relationship between the two. The internet became even more invested in the interaction when Evans responded to Lizzo's DM. Luckily, Lizzo kept fans in the loop by posting an update to TikTok. Evans empathized with Lizzo, messaging back "No shame in a drunk DM 😘 god knows I've done worse on this app lol 🤦🏻‍♂️." He was likely referring to the time he accidentally leaked his own nude photo.

The banter did not stop there — Lizzo posted another hilarious TikTok where she pretended to be pregnant with the actor's baby. Evans responded to Lizzo's "pregnancy" via Twitter DMs, stating "Hi! Just heard about our little bundle of joy my mother will be so happy lol." Although the two are not officially dating, fans love the Chris Evans and Lizzo dating rumors.

Lizzo's exchange with Chris Evans was only one of the many times she flirted with a celebrity crush on social media. She has a history of DM-and-delete exchanges with Hollywood's most eligible bachelors, as Lizzo is not afraid to make the first move. The "Truth Hurts" singer detailed the moment she DM'ed Drake in a 2019 interview on Busy Philipps' "Busy Tonight." She explained that although she quickly deleted the message, it earned her a follow from the rapper. "I was drunk and I was just like, 'Let's just see if this motherf***er can sing.' And I sent him a DM ... this was a while ago. And then I unsent it, and then he followed me after that," Lizzo said in the interview. Although this Instagram interaction did not play out on TikTok, the end result was just as successful. Drake was intrigued enough to follow Lizzo back.

The musician's love for Drake continued when she referenced the Canadian rapper in her hit single "Rumors," writing "No, I ain't f*** Drake yet." In an interview with Zane Lowe, Lizzo jokingly said the lyric was an attempt to manifest the rapper into her life. "I just thought it would be so funny to say," she explained. "I have a small relationship with him, he's very cool." So, it seems Lizzo and Drake are just flirty friends.

There has been a lot of social media buzz about the celebrity dating app Raya, and curious fans speculate which stars are active there. Celebs like Demi Lovato said they've used the app to search for love in Hollywood, while many famous faces have been transparent about not finding love on Raya — and Lizzo is no exception. When Busy Philipps asked about Lizzo's dating life, she revealed she had used Raya in the past. She explained that she tried to match with John Mayer but was unsuccessful. Like many of us, Lizzo has yet to find love on dating apps.

However, the star has been known to get cute and flirty with fellow celebs like Harry Styles and Trevor Noah. It was at the 2020 Brit Awards that Lizzo and Styles held hands and cuddled up in the midst of her interview with host Jack Whitehall. And it was on an episode of "The Daily Show" that she twerked and kissed Noah on the cheek, as only Lizzo can do.

In March 2021, Lizzo was spotted snuggling with a mystery man in Malibu. The Shade Room broke the news with a series of steamy photos that showed the pair getting close on a balcony. This was the first time the two were spotted together publicly, so fans had no idea who Lizzo's new arm candy was. As a result, dating rumors and speculation spread quickly. The pair seemed to be closer than friends in the intimate pics, so many assumed this mystery man was Lizzo's new boyfriend.

The singer set the record straight when she clarified her relationship status in an Instagram video captioned "SINGLE." In true Lizzo fashion, the video featured the stunning songstress showing off her body in a revealing two-piece set. It seemed that she really wanted to put the relationship status speculation to an end. However, it appeared the same man accompanied the singer in October 2021, as the two were photographed leaving a Beverly Hills restaurant. We never found out who exactly this handsome mystery man was, and Lizzo's dating life remained private following these sightings.

As of this writing, Lizzo appears to be living the single life, but she got personal about the details of her love life for the first time in a 2020 Rolling Stone interview. She spoke on dating as a size-inclusive woman and how this affected past relationships, explaining she fell in love for the first time at 19, but the relationship ended in heartbreak. She suggested her partner wanted her to change. "I remember he was like, 'I'm a little guy. I need a little girl,'" she said. This led the singer to attempt to emulate the type of woman her partner wanted, but, as she was looking to Zooey Deschanel for inspiration on what she "should" look like, she realized, "I can't just wake up and be a white girl."

During an appearance in her hometown of Detroit, the songstress revealed to the crowd the unnamed inspiration behind her hit "Truth Hurts." "Y'all want to know a secret? The person I wrote that song about is from Detroit."

Two years prior to Lizzo's Rolling Stone interview, she thought she'd found true love again. Unfortunately, this relationship came along at the wrong time in her life. This time, however, the musician didn't let heartbreak bring her down. "As f***ed up as it sounds, I needed that heartbreak experience," she explained. This was a learning opportunity that led Lizzo to change her perspective on love and relationships, using those experiences to become the confident and charismatic superstar she is today.