A Timeline Of Jack Harlow's Flirtiest Moments

Jack Harlow’s had his fair share of flirty moments in the spotlight. On Nov. 22, the “Vanilla” rapper went on Alex Cooper’s Call Her Daddy and discussed his celebrity crushes — though he played it coyer than usual when it came to name-dropping.

“There’s someone” Harlow told Cooper, “but I don’t think it’s mutual, so I don’t really want to talk about it.” He added, “She’s beautiful.”

“I like a girl next door. I don't need any internet presence, I like me a librarian. I like a waitress,” Harlow added. Cue the fan theories about who he could be referring to — and TBH, there are a lot of potential A-listers to sort through (though none are librarians or waitresses).

Throughout his years in the spotlight, Harlow hasn’t shied away from public flirtation. If anything, he’s embraced it. Whether he’s talking up a fellow rapper on the red carpet or sneaking an “I love you” into an interview, Harlow has proved himself to be a ladies man, through and through.

Here’s a full rundown of his rizz-filled celeb encounters.

2020: Doja Cat

Back in March 2020, Harlow was on Instagram Live when he noticed Doja Cat tuned in. He invited her to “come on in here,” and things got flirty fast. Apparently, Doja’s boyfriend resembled Harlow — leading some fans to speculate that Doja and Harlow were together. (Spoiler: They weren’t.)

When Doja left the Live, Harlow said “love you” to her. He then confessed to the 14,000 fans still watching, “I’ve had a crush on her for months.”

A couple years later, at the 2022 Billboard Music Awards, Harlow said he was “cool with Doja” — even if she did leaving him hanging on IG.

April 2021: Addison Rae

In April 2021, Addison Rae and Harlow were spotted together at a boxing match in Atlanta, Georgia. Soon after, Rae began liking multiple Instagram posts on Harlow’s account and started following some of his friends. In a photo shared to Harlow’s Instagram story around the same time, he was pictured sitting with Pete Davidson after his appearance as the musical guest on SNL. Fans thought the woman’s hand in the photo belonged to Rae.

For his part, Harlow was caught seemingly talking about Rae in an interview with Pitchfork released after their rumored encounter. In the since-deleted clip, Jack admitted he was FaceTiming “a TikToker” the night prior to the interview.

“I was going through her page with her and, before I had sat and really looked through her videos, I was like, ‘She’s cute, lighthearted,’” Harlow recalled in the since-deleted clip, per Sportskeeda. “I started watching the videos and her sex appeal just came out. I really like it because it activates something. I like the faces that are made, I like the hip movements.”

However, on April 19, 2021, Rae took to Twitter with a simple “I’m single” to shut down the dating rumors. She was fresh out of a relationship with Bryce Hall. “Right now is my time to focus on me,” Rae told SiriusXM’s The Morning Mash Up, per Entertainment Tonight.

June 2021: Saweetie

At the 2021 BET Awards, Harlow introduced himself to fellow rapper Saweetie on the red carpet. They held hands the entire time they spoke, leading fans to think there could be a romance brewing.

But after Saweetie had left the BET red carpet, Harlow explained that he was not, in fact, shooting his shot with her. “That was me saying ‘hello,’” he said. “That’s a friend vibe.”

May 2022: Emma Chamberlain

Emma Chamberlain and Jack Harlow have had quite a few flirty moments. Their first interaction happened at the 2022 Met Gala, where Emma was doing interviews for Vogue on the red carpet.

Harlow stopped to chat with Chamberlain, and she apologized for not being ready. “Sorry, I’m, like, reapplying my makeup. One moment,” she told him. Harlow replied, “You did a great job.”

The duo ended their conversation by trading “love ya”s.

The following May, they had a similar moment at the 2023 Met Gala. When Chamberlain questioned how they would “outdo” their previous interview, Harlow replied, “We don’t have to. It’s just… it’s us. It’s a timeless partnership.”

Again, they said they “love[d]” each other before saying goodbye.

May 2022: Dua Lipa

In May 2022, Jack made his feelings about Dua Lipa crystal clear when he released a song named after the singer. In the track, he sang, “Dua Lipa, I'm tryna do more with her than do a feature.” Later in the song, he sang, “I sold them basements out, let's do arenas, crushin' / She looking, I'm blushing, I'm lying, I'm touching.”

Harlow explained the song during an appearance on The Breakfast Club podcast that May — and according to him, Lipa had an awkward reaction to the lyrics. “I wanted to get her blessing, so I FaceTimed her and played it for her because I didn’t want her to be blindsided by that or feel like creeped out or anything,” he recalled.

“If she had said, ‘Yo, I hate it. I don’t want it to come out,’ it wouldn’t have come out. She was like, ‘Oh, I mean it’s not my song. I suppose it’s OK.’ She was just kinda thrown off and she just kinda let it go,” he added.

But things seemed to pick up between Harlow and Lipa when they met at the Variety Hitmakers Brunch in Los Angeles on Dec. 3, 2022. According to Page Six, the duo was in “constant communication” after their IRL meeting. On Dec. 12, a source told the outlet, “[Harlow] was very interested in her, and was going to strongly pursue [the romance].”

On Dec. 13, 2022, an insider told Us Weekly, “They like each other and are both excited to see where things go next.”

But their rumored romance didn’t go much further. A few months later, in February 2023, Lipa hard-launched her relationship with Romain Gavras.