Before their split, the pair navigated through both envy-inducing high points and rockier patches, with plenty of social media documentation and cameras rolling.
Low: Pre-romance rumors and criticism
Kyga had to deal with backlash from haters even before they officially announced their relationship. In February 2015, Amber Rose, who is best friends with Blac Chyna, the mother of Tyga's child (more on that later), slammed the rapper for his alleged involvement with the then-17-year-old.
"Kylie's a baby," Rose said on New York's Power 105.1. "She needs to go to bed at 7 o'clock and relax. It's ridiculous. Tyga should be ashamed of himself. That's how I feel, for sure. He has a beautiful woman and a baby that he left for a 16-year-old who just turned 17."
Jenner's older sister Khloé jumped to her defense on Twitter. "Please don't worry about my sister, who has a career and her s--- together at ONLY 17," she wrote. "Please stop talking about us in interviews mama. None of us talk about you."
High: Confirming their relationship
In March 2015, Tyga put an end to months of speculation and finally announced the pair's couplehood with a sweet Instagram post.
"Certain things capture your eye, but only few capture the heart," he captioned a pic of Jenner.
High: Birthday baes
Tyga made sure his girl celebrated in style when she turned 18 in August 2015. He marked the special day with a sultry Instagram tribute to "the dopest girl ever" and surprised her with a $320,000 Ferrari during her big bash at Bootsy Bellows in West Hollywood.
Low: Family vacation drama
Tyga tagged along for the Kardashian-Jenner summer trip to St. Barts, but not everyone in the krew was happy about the lovebirds' behavior.
Courtesy Kylie Jenner
"This is the first time I'm bringing a guy on a family trip, so I'm a little nervous about how it's going to go," Jenner confessed on Keeping Up with the Kardashians.
Her fears proved valid when sister Kendall slammed her vacay PDA. "You could have taken this time to be with your family," she said.
TRB / EKNY / FAMEFLYNET PICTURES
Low: Financial woes
The rapper has contended with a number of financial issues throughout his relationship with Jenner. His landlord sued him for $70,000 in back rent on a home near Jenner's mansion in Calabasas. Tyga countered the suit with a breach of contract lawsuit.
In September 2015, the state of California claimed Tyga owed them over $19,000 in back taxes.
Recently, Radar reported that they obtained court documents proving Tyga filed for bankruptcy in 2010. Meanwhile, TMZ reports that a repo company is after Tyga's 2013 G-Wagon following missed payments.
High: Music video bliss
Jenner has starred alongside her man in two of his music videos. The first one, "Stimulated," was released shortly after her 18th birthday and offered a steamy glimpse at their relationship.
"They say she young, I should've waited / She a big girl, dog, when she stimulated," he raps in the video.
Then in Tyga's video for "Dope'd Up," the reality starlet tested her acting chops in a horror-movie-inspired scare-fest.
Low: A brief breakup
A number of sources confirmed to PEOPLE that Kyga had come to an end in November 2015 after the rapper "broke her trust."
GVK / Bauer-Griffin / GC
"She's caught him lying and talking to other girls behind her back before, and this was the last straw," one source said, adding that she "feels super betrayed and is just so pissed off, damaged and hurt about it."
But just a day after the new broke, a source told PEOPLE "they're very much back on," as Jenner held hands with Tyga and asked fans to "chill" on Snapchat.
"She took him back after he begged for her forgiveness," the source said. "He claimed that everything was misinterpreted and a huge misunderstanding."
An episode of KUWTK filmed around the time of the temporary split revealed Jenner's uncertainty about the relationship. "I just, like, don't know what to do about T," she told her sisters through tears.
Low: Blac Chyna tension
Blac Chyna, who is the mother to Tyga's 3-year-old son King Cairo, has been involved in a number of spats with the couple.
Many fans cried shade when Jenner posted a photo of herself in a crop top, tight pants and sneakers an hour after Blac Chyna shared a selfie in a nearly identical outfit in May 2015.
In September, Tyga seemed to blame his ex for spreading rumors when he took to Instagram to reference reports that he had actually leased Jenner's Ferrari. "When the hating don't work they start telling lies. #WhereYoFerarriTho?" he wrote.
Blac Chyna's BFF Amber Rose didn't take long to hit back with her own post. "She don't need a Ferrari, she can drive mine," she captioned a pic of her pink ride.
"We drive our own whips peanut head," Tyga retorted with a photo of his Bentley.
The drama reached an all-time high in 2016 when Jenner's brother Rob Kardashian began dating Blac Chyna. "Kylie is livid," a source told PEOPLE when news of the romance broke. "She feels super betrayed and can't understand why someone in her own family would stab her in the back like that."
As the tension continued into the next month, Blac Chyna appeared to accuse Jenner of stealing her idea for a cooking project.
"B---- Bye," the model captioned a screenshot of her Insta account dedicated to cooking after Jenner announced her own cooking segment. "I'm trying to figure out what else can I create so other people can imitate. Any suggestions?" she later joked on Snapchat.
High: Wedding bell tease
During a January 2016 appearance on Kocktails with Khloé, Tyga alluded to another milestone with Jenner when he said "I would marry her."
"Yeah for sure. Yeah. Y'all know that," he said when asked if he "really" wanted to marry Jenner, making Kyga fans everywhere go wild.
Low: Cheating accusations
In January 2016, 14-year-old aspiring model and singer Molly O'Malia claimed that Tyga had sent her "uncomfortable" messages on social media. The rapper's manager told TMZ he had initiated contact to discuss signing her to his record label, and that she said she was 17.
"I began to feel uncomfortable when he asked me to FaceTime with him," O'Malia said in a statement. "He asked me to FaceTime three times, but I did not do it. Because of my discomfort with why he wanted to communicate with me, I quickly stopped responding to him. It's crazy how so much can come out of nothing."
Later in the month, a source revealed to PEOPLE that allegations that Tyga had cheated on Jenner with Brazilian model Annalu Cardoso caused a rough patch in their relationship.
"They are together, but aren't on the best terms," the source said about Kyga.
"They have a very 'high school' relationship and argue and bicker all the time about stuff for no reason, and that's because Kylie doesn't trust Tyga after all the reports came out about him cheating," they added.
High: All the PDA
High: Playing Nice with Blac Chyna
Jenner and Blac Chyna put rumors of bad blood behind them after the model's engagement to Rob Kardashian.
"When we've been best friends the whole time," Jenner captioned a Snapchat selfie of her and Tyga's ex.
Kylie Jenner / SnapChat
Chyna shared a friendly photo of her own, writing "Hanging out with my lil sis," alongside a face swap.
Blac Chyna / SnapChat
Not long after the apparent reconciliation, Chyna and Kardashian announced they are expecting a baby together. "The girls were super shocked at first about the pregnancy news, especially Kylie," a source told PEOPLE about Jenner's reaction to learning she has a new niece or nephew on the way. "But at this time, Kylie especially was pushed to swallow her pride and support her family, even if she didn't want to. She's doing it for the greater good of everyone involved."
Low: Another Split
On Thursday, PEOPLE confirmed that Jenner and Tyga have broken up once again after almost two years of dating.
Before the split, the pair was last seen together at the Met Gala on May 2, where they shared a table but walked the red carpet separately.
The day before news of the breakup was announced, Jenner had a rare candid moment on Snapchat. "I never really like to show people my personality or all of me. 'Cause, I don't know, Kylie Jenner is who you see on Instagram, but I am not Kylie Jenner," she said, adding "The real Kylie Jenner is sensitive, weird, and … I don't know, I love really hard."