If there’s one thing that keeps the Kardashian’s relevant, it’s the mystique surrounding their dating lives.

Entertainment outlets such as TMZ, Cosmopolitan, US Magazine, and E! love to keep the cameras on the Kardashian/Jenner klan on a day-to-day basis to keep the public, fans, and their readers speculating over who’s currently dating who.

With Kim and Kourtney Kardashian settling down in recent years with beautiful children, there are now only a handful of Kardashian/Jenner’s still experimenting in the dating market.

Here are 7 beautiful men Kylie Jenner has dated.

7. Lil Twist

In July of 2013, Kylie Jenner was rumored to be dating Young Money rapper and Lil Wayne prodigy Lil Twist. The pair was first spotted together in Kylie’s hometown of Calabasas, CA heading into a one-on-one movie date to see the horror film, The Conjuring. A few months later on January 13th, 2014, Daily Mail reported that Kylie had arrived at Lil Twist’s 21st birthday at the Philippe restaurant in Beverly Hills. 

6. Jaden Smith

Kylie and Jaden were seen making out at older sister Kim’s wedding back in May of 2014. Sources close to both of them claim that the pair grew up together and were each other’s first real loves. Later that year, Kylie co-starred in Jaden’s Blue Ocean music video where the two can be seen hugging and kissing, cementing their relationship as more than “just friends”.

In an interview with Sydney Australia’s Kiis FM radio station, the pairs mutual friend, Australian actor Lincoln Lewis, referred to Kylie as “Jaden’s missus” before trying to backtrack his statement.

5. Miles Richie

The Kardashian’s and the Richie’s are family friends dating way back. Kylie and Miles have been seen in public together on numerous occasions throughout the summer of 2014. Reports of a possible relationship sparked when Kylie was videotaped tattooing her initials onto Miles’ hand at a Hollywood recording studio. As pictured below, the pair was also spotted near kissing inside of Miles’ SUV on the way back from a day of errands. 

4. Cody Simpson

Kylie and Cody, known to their fanbases as “Kody”, briefly dated in their early teen years when they were both 14-years-old. The pair met at the Hollywood premiere of Breaking Dawn: Part 1 when Kylie and her sister, Kendall, had interviewed him for Ryan Seacrest’s radio show. When pressed, Kylie noted that she would marry an Australian, hinting that she found a liking in the Australian singer.  

3. Justin Bieber

Once Kylie came back to the U.S. from her sister Kim’s wedding at the Forte di Belvedere in Florence, Italy, her closeness with pop-sensation Justin Bieber reached new heights. The pair was spotted together in several junctures including dinner for two at The Rainbow on Sunset Blvd in May of 2014 after having spent the night together at the MGM Grand in Las Vegas for the Floyd Mayweather vs. Marcos Maidana fight earlier in the month. 

 2. PartyNextDoor

Following a highly publicized split from her longtime beau Tyga, Kylie swiftly moved onto another rapper, Canada’s PartyNextDoor. The swift changeup mixed in with a Snapchat story of PND singing “Kylie, oh Kylie”, and an Instagram pic of the two showing off their Rolex watches at what appears to be a restaurant, sent the hollywood gossip scene into an all out frenzy. The pair was spotted again in May of 2016 leaving Russel Simmon’s All Def Comedy live at the TCL Theatre in Hollywood. 

1. Tyga

Where does one even begin…

Kylie’s on-again, off-again relationship with Tyga is her latest and longest documented romance to date. The pair are routinely keeping fans updated of their whereabouts on Snapchat, Instagram, and appearances at various restaurants and gigs. Despite the overbearing hate their relationship received for their age difference (Kylie being 17 at the time, Tyga 25), the two seemed to have stuck it out to the haters through their public affection for one another (especially seen in Tyga’s music video for “Stimulated”).