Keeping Up With Kylie: Kylie Jenner’s Special Dating History

Kylie Jenner wears huge lilac pom-pom sleeves, a transparent, off-the-shoulder patterned dress and poses on the red carpet.
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Mar. 23 2020, Published 3:51 p.m. ET

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Without a doubt, Kylie Jenner is in the running for hardest working woman in reality TV. Not only does she appear in Keeping Up with the Kardashians and her spinoff series Life of Kylie, she also the founder/owner of Kylie Cosmetics, has twice been named by Time as one of the most influential teens in the world, and was featured on the cover of Forbes magazine as the youngest self made billionaire. How does she find the time to date with such a busy schedule?

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MORE: Kylie Jenner Says She Wants More Babies After Split From Travis Scott

Somehow her dating schedule is even busier. From Lil Twist to Tyga, Jenner has been looking everywhere for love. She’s dated Jaden Smith and Cody Simpson. She settled on rapper Travis Scott for a bit, even having a baby girl with him. But even that relationship has ended and restarted, then stopped again. It gets complicated.

MORE: Back Off, Drake? Travis Calls Ex-Galpal Kylie His 'Wife' During Music Fest Reunion

Kylie is pushing head first through Hollywood and leaving a stream of boys and men behind her. Check out this gallery of guys who have been left in Kylie Jenner’s wake.

1. Ramsey IV.

Kylie Jenner poses alongside sisters Kendall Jenner and Khloe Kardashian and her parent.
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Jenner was so young that the public barely even knew who she was when she dated her first boyfriend. His name is Ramsey IV, and there was puppy love when they were an item back in 2008. Jenner was just 11 at the time.

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2. Cody Simpson.

Kylie Jenner, in an off-white blouse, poses on the red carpet alongside sister Kendall who wears a peach-colored dress.
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Jenner briefly dated Australian singer Cody Simpson back in 2011. Simpson later joked he was glad it didn’t last because their celebrity name would have been “K-O-D-Y” and that “didn’t work for me.” Good call, Cody. Jenner, on the other hand, denied there was ever a relationship saying, "Cody and I are just good friends. We can say that as much as we want and people will still listen to gossip."

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3. Jaden Smith.

Jaden Smith, in all-black, stands next to Kylie Jenner who wears a bejeweled peach dress on the red carpet.
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Around March 2013, when he was 14 and she was 15, Jenner began dating her friend Jaden Smith. Us Magazine broke the story when a source told them “They’re dating. It’s new, but they’ve been friends forever. Only they know when they split up but when they were seen at Justin Bieber and Hailey Baldwin’s wedding together, rumors sparked.

Around March 2013, good friends Jaden Smith and Kylie Jenner became a little more than friends. He was just 14, and she was 15. Us Magazine broke the story when a source told them, “They’re dating. It’s new, but they’ve been friends forever.” Rumors sparked when they were seen at Justin Bieber and Hailey Baldwin’s wedding together.

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4. Lil Twist.

Lil Twist, in a black patterned shirt and sunglasses, holds earphones up for the camera.
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Jenner was linked to rapper Lil Twist for a hot minute in 2013. This courtship took place for all to see on the internet. Most of the action took place on Twitter where they openly flirted with each other.

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5. Tyga.

Tyga, in shades, baseball cap, and black leather jacket sits next to Kylie Jenner who wears a grey patterned dress.
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This was possibly Jenner’s first real relationship in that it lasted a couple of years, from 2014-2017. They initially met in 2011 at older sister Kendall Jenner’s Sweet Sixteen party where Tyga was performing. Perhaps because Jenner was under-age when they began dating (she was 17), Tyga kept denying they were a thing but, almost magically, when Jenner finally turned 18, Tyga made their relationship official on Instagram.

Things changed with Tyga. This relationship lasted from 2014-2017. The pair initially met in 2011 at Kylie’s older sister Kendall Jenner’s Sweet Sixteen party where Tyga was performing. Tyga vehemently denied dating the then 17-year-old — and underage — Jenner. Even with the denials, fellow celebs such as Amber Rose came down on the rumored relationships. But as soon as Kylie turned 18, Tyga bought her a $320k Ferrari, then they took to Instagram and made the relationship official.

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6. PartyNextDoor.

PartyNextDoor performs on stage while wearing a black shirt with white flowers on it.
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Kylie and Tyga’s relationship had a few ups and downs. During one of the downs, Jenner allegedly briefly dated PartyNextDoor. In 2016, she appeared in the music video for his track “Come and See Me” and made out with him on camera. But was the whole thing just an attempt to make Tyga jealous? Jenner said, “Me and Party have a cool relationship. I think he’s so talented and I love his music. But I wouldn’t say we dated. It never really got to that boyfriend-girlfriend stage. It was just fun. I was doing what I wanted to do.”

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7. Travis Scott.

Travis Scott, in a chocolate brown suit with black tie, kisses Kylie Jenner, who wears a white dress, on the red carpet.
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Just weeks after Jenner officially split from Tyga, she had already moved on and was seen at Coachella holding hands with Houston rapper Travis Scott. Turns out the connection was so intense that Jenner hit the road with him, joining his tour. Within just five months, Jenner was pregnant with their baby daughter Stormi, born in February 2018. Then, Jenner allegedly found some inappropriate DMs that Scott was sending to other women via his Instagram. Scott denied cheating but temporarily suspended his Instagram account and canceled a show. In October 2019, it was reported that Jenner and Scott had broken up. According to reports, the pair were “walking away from their relationship” despite “trying to make the relationship work for a while.” The week they broke up, Jenner was spotted back with Tyga.

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8. Drake.

Drake stands on stage, holding a mic, wearing a top with a Stone Island logo.
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In late October 2019, Kylie was seen cozying up to Drake. A source told Us Magazine, “At his Halloween party, they were affectionate and clearly there together. They’ve been seeing each other romantically. He also showed up to Kendall Jenner’s birthday.” Even so, she has not been seen much publicly with the Toronto native immediately after. As far as the men in Kylie’s life go, all she’s saying is she remains dedicated to coparenting with Travis Scott.

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