Kylie Jenner’s dating life is once again the main tabloid story. After splitting up with the father of her daughter Stormi, Travis Scott, the rumors appeared that the youngest of the Kardashian-Jenner family is dating 11-years-older rapper Drake.
One thing is for sure, Kylie has been busy when it comes to her dating. The 22-year-old star dated some of the hottest and most talented men in Hollywood.
Here is the list of all men Kylie Jenner reportedly dated.
1. Justin Bieber
Justin Bieber and Kylie have a long history, and it was often rumored that the two dated in the past. Bieber and Kylie were first spotted getting cozy at the Coachella Music Festival back in 2014. They’ve also been photographed on romantic dinner dates out in Hollywood, and they were watching the Floyd-Mayweather fight together in Las Vegas. Although these two insisted they were just friends, it was hard for their fans to believe in that.
2. Cody Simpson
Back in her early teens, Kylie had a relationship with singer Cody Simpson. Their young romance made headlines when photos of the couple hugging and kissing leaked to the tabloids. During their relationship, their fans gave them the nickname “Kody”. But this relationship didn’t work out, despite the enthusiasm that Kylie’s fans had.
3. Jaden Smith
Rumors began to spread in 2013 that Kylie had moved on from Cody Simpson and was involved with rapper and model Jaden Smith. It didn’t take long for those rumors to be confirmed when Hollywood stars were seen leaving a movie theater holding hands. The relationship was shaky for about a year, but things started to heat up when they were spotted kissing at Kim Kardashian and Kanye West’s wedding in 2014. Kylie even made an appearance in the music video for Jaden’s song “Blue Ocean” as a way to confirm their relationship.
4. PartyNextDoor
Kylie obviously has a thing for rappers. She also dated Canadian artist PartyNextDoor. The rapper hinted the romance on a Snapchat story where he serenaded the reality star by singing “Kylie, Oh Kylie”. Their romance was officially confirmed when Kylie appeared in PartyNextDoor music video for the song “Come and see me”. At the end of the video, Kylie and the rapper shared a steamy kiss in the rain, but this relationship also didn’t last.
5. Shamari Maurice
Shamari Maurice and Kylie Jenner have been friends for years, but many suspected their relationship went from BFFs to more than friends at some point. Kylie even fueled the romance rumors by posting photos of Shamari on her Instagram with captions such as: “He loves to cuddle with me”. The two traveled together, held hands all over the city, and photograph themselves cuddling on numerous occasions.
6. Stitches
Miami rapper Stitches allegedly got dumped by Kylie, and the end of their fling made him go crazy. He claimed Kylie cheated on Tyga with him just weeks after her 18th birthday. He described their encounter in a song called “Kyga She’s A Liar”. He claimed they did drugs and had a night of fun. He also stated that Kylie didn’t feel remorseful about cheating on Tyga. Stitches said he felt the need to put his fling with Kylie on blast because she blocked his number and completely ignored him the day after they hooked up.
7. InkMonstarr
Stitches recruited Florida rapper InkMonstarr to appear on the song “Kyga She’s A Liar” because apparently InkMonstarr had hooked up and had been dumped by Kylie too. InkMonstarr claims to have proof about his moment of fun with Kylie, but the only thing he had was a screenshot of a strictly platonic direct message between the two of them. After their alleged hookup, Ink began to bash Kylie’s plastic surgery and her promiscuity.
8. Lil Twist
In 2013, the Kylie and Lil Twist rumor started to hit every gossip magazine, and the two were spotted going on dinner and movie dates in Kylie’s hometown of Calabasas California. Kylie showed up to Lil Twist’s 21st birthday party, but the relationship wasn’t built to last.
9. Miles Richie
During the summer of 2014, Kylie got close to Miles Richie, the son of singer Lionel Richie. Kylie denies most of her relationships, but it was difficult for her to deny her romance with Miles. The couple made headlines after they were spotted driving around Los Angeles together, but their relationship was officially confirmed when Kylie was photographed tattooing her initials on Miles’s hand.
10. Tyga
Before turning 18, rumors that Kylie was dating rapper Tyga hit all the tabloids. They denied their relationship to the press, but they didn’t try too hard to keep their romance a secret. As soon as Kylie turned 18, the two went public. They frequently shared snippets of their relationship on their social media accounts, and they were surprising each other with lavish gifts, like luxury cars and expensive jewelry. Her family reportedly wasn’t too pleased with her relationship with her much older boyfriend.
11. Travis Scott
Kylie and Travis Scott were first seen together in April 2017 at the Coachella Festival, after which she joined him on tour. Within a month, Kylie was pregnant. She gave birth to Stormi in early February, and their relationship seemed idyllic to the fans. The media speculated about their wedding, but it didn’t happen. Kylie Jenner confirmed in early October that she and Travis Scott broke up, but they have remained friendly as they co-parent their daughter Stormi.
12. Drake
Although she broke up with her daughter’s father, Travis Scott, just over a month ago, tabloids are already reporting that Kylie Jenner seems to have found a replacement – 11-years-older rapper Drake. The tabloids are also suggesting that Kylie is spending time with Drake to make her ex-boyfriend jealous. The two live in the same neighborhood and have been hanging out almost daily since Kylie broke up with Travis. A source close to Jenner told PEOPLE that she “doesn’t seem to be dating, but she sees Drake occasionally, although it doesn’t seem serious”.
Kim Marks 
Nina Smith