Kylie Jenner and Tyga Break Twice

The pair, who has  dated on and off since 2014, has broken up. Jenner, 18, and the 26-year-old rapper called it quits  before the 2016 Met Gala in early May, TMZ first reported. The first-time gala attendees walked  the red carpet separately.

"It was a long  time coming," a source told E! News after confirming the breakup. All of their relationship's  drama "takes its toll," the insider added.

"Their relationship  is complicated," a second source shared with E! News. 

The reality star  began dating the "Rack City" rapper in October 2014, though it has been a rocky romantic road for  the duo. On Tyga's 26th birthday in November 2015, the pair surprisingly split. According to a  source, Jenner's former beau was "devastated."

"They are on a  break," an insider told E! News at the time. "They were just a week or so ago talking about ‘ever after'  and things got messy this past week. Kylie wants time to just be by her self and do her. Tyga is not  giving up as that's his one and only lady."

However, just five  days later, the reality star appeared on The Ellen DeGeneres Show to confirm they were back together.

"No, honestly people  have it all wrong," Jenner told the daytime talk show host. "No. We're not broken up."

"We're just like...I  don't know. Hanging out. Living life," she added. When DeGeneres was confused by the explanation, Jenner  declared, "We're still together."
Kylie Jenner,  Tyga, Kris Jenner's 60th Birthday Party






Fast forward  into February and Tyga was back to publicly declaring his affection  for the makeup mogul. "I love that girl," he said during a radio interview  with Real 92.3 in February.

Now,  with the news of their second split, sister Khloe Kardashian's remarks to  E! ring truer than ever.

"I ask Kylie...'I think  you were just somewhere for New Year's with him' and then like  one day, they're not together," Khloe told E! News' Catt Sadler  exclusively in January. "That's the life of an 18-year-old...So I stopped  asking her, because it's confusing and I hate telling people, 'Oh, they  broke up' and then all of a sudden, someone pulls in my driveway and  I'm like, 'Oh, s--t, I thought we were done with this one.'"

"I'm just as  confused!" Khloe said, joking, "I need like a 'Note to self, who is everybody dating in this family.'"