At every step of Kylie Jenner and Travis Scott’s more than two-year relationship, they’ve kept fans guessing. Are they dating? Is she pregnant? Will he propose during the Super Bowl halftime show? On the heels of the couple’s reported “break,” fans are left wondering what happened and if the split will last. Here, a breakdown of their closely-watched romance.
April 2017: Shortly after Jenner’s split with on-again, off-again boyfriend Tyga, the cosmetics mogul was spotted hanging with Scott at a Coachella party. But there apparently wasn’t “Love Galore” between these two just yet. Per a People source, “[Scott] and Kylie have also been friends for a while, and they all hang out. When she and Tyga are having drama, she tries to make him jealous by hanging out with other guys.”
Later that month, photos emerged of the secretive couple sitting court side at an NBA Playoffs game. Also noteworthy: the game took place in Scott’s hometown of Houston.
Jenner and Scott capped off their whirlwind month in Boston, per E! News. The outlet reported that the blossoming couple spent the weekend there, where Scott was performing two shows. Hours later, Page Six ran a report that Jenner was at Cipriani in New York City for Scott’s 25th birthday party.
May 2017: Photos of Jenner and Scott in Miami, for his performance at Rolling Loud Festival, proved that their flirtation showed no signs of seizing. An insider even told Us Weekly at the time that “Travis is telling friends that he and Kylie are a real deal.” Another told the outlet that the two “really looked like a couple” at Scott’s recent birthday party.
While the relatively new couple didn’t walk the Met Gala red carpet hand-in-hand (yet), the event marked a major milestone. Jenner shared a group snap from the evening, which included her sister Kendall and friend Jaden Smith, among others. Just slightly visible in the frame was Scott, making them sort of Instagram official?
June 2017: If there was any indication that these two were getting serious, this was it. Scott and Jenner debuted small, matching butterfly tattoos on Snapchat, June 12. The musician perhaps hinted at the permanent ink, timed with the release of his song “Butterfly Effect,” a month earlier. In May, he posted a distant photo of Jenner boarding a private jet with the caption, “BUTTERFLY EFFECT ?????.”
July 2017: Jenner continued to prove her groupie skills while attending Scott’s performance at Wireless Festival in London. Kendall and Bella Hadid also joined to cheer the rapper on.
August 2017: After Jenner watched Scott perform with Kendrick Lamar at the Staples Center, she was treated to a surprise 20th birthday party. Ever the supportive boyfriend, Scott was on hand for the festivities, although he chose to stay slightly hidden in Khloé Kardashian’s birthday post for Jenner.
September 2017: September 22 is when Jenner and Scott’s relatively low-key relationship became decidedly high-profile. TMZ first broke news that Jenner was reportedly pregnant. The outlet also claimed that Scott had been telling his friends about the development. Later that day, Page Six ran a report that Jenner was expecting a girl and about four months along. The following day, Jenner was pictured at the iHeartRadio Music Festival in a baggy t-shirt, which was confirmation enough for some corners of the internet.
December 2017: Throughout the end of 2017, speculation about Jenner’s rumored pregnancy intensified. Fans scoured her Instagram feed for clues, and many drew their own conclusions when Jenner was absent from the Kardashian Christmas card. However, both kept mum on the possible news. When asked about potentially becoming a father during a Billboard cover interview, Scott responded, “I don’t want to talk about that.”
February 2018: In February, it was the storm after the quiet. Jenner and Scott’s first child together, Stormi Webster, was born on February 1. Three days later, she announced the birth (and confirmed her pregnancy, naturally) with an Instagram post and video entitled, “To Our Daughter.”
Jenner had this to say in her initial post regarding the privacy of her first pregnancy:
“I’m sorry for keeping you in the dark through all the assumptions,” she wrote. “I understand you’re used to me bringing you along on all my journeys. My pregnancy was one I chose not to do in front of the world. I knew for myself I needed to prepare for this role of a lifetime in the most positive, stress free, and healthy way I knew how. There was no gotcha moment, no big paid reveal I had planned. I knew my baby would feel every stress and every emotion so I chose to do it this way for my little life and our happiness.”
“Pregnancy has been the most beautiful, empowering, and life changing experience I’ve had in my entire life, and I’m actually going to miss it. I appreciate my friends and especially my family for helping me make this special moment as private as we could. My beautiful and healthy baby girl arrived February 1st and I just couldn’t wait to share this blessing. I’ve never felt love and happiness like this I could burst! Thank you for understanding.”
For his part, Scott tweeted, “2.1.18 4 ever New rager in town. !!!” Days later, Jenner also posted a photo of her daughter grasping her finger, alongside confirmation of the baby’s name.
A source told People at the time that the couple was focused solely on Stormi, not moving in together or marriage. “Kylie and Travis are not officially living together,” an insider told the outlet. “He has his own place. They are co-parenting though, and things are going great. They are together and happy. They’re not in rush. They’re just enjoying their little family.” At the end of the month, the new parents were spotted dining at Nobu alongside former bestie, Jordyn Woods. They arrived in Jenner’s black Ferrari push present.
March 2018: Scott gets in on the Instagram action, posting the first photo of Stormi, with the caption, “Our little rager !!!!”
Jenner and Scott are also spotted boating in Miami this month. A People source explained that spending time together, when not with the baby, was a major priority. “Despite being new parents, Kylie and Travis are still in a new relationship too,” the insider said. “Kylie is happy with their living situation. Travis is a great dad. When he wants to work, Kylie is supportive.”
April 2018: At the end of their first year together, the couple celebrated a few milestones. They flew out to Texas to introduce Stormi to Scott’s family. Jenner also shared on her Instagram Stories that she’d rented out Six Flags for Scott’s 26th birthday. The couple even found time to return to Coachella, the initial start of their romance the year before.
May 2018: At the start of the month, Jenner and Scott vacationed in Turks and Caicos with Stormi. “birthday behavior,” she captioned an Instagram post of the two on a boat.
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Like Coachella, the new parents returned to another important event from their relationship’s early days. The couple’s first official red carpet appearance was at that year’s Met Gala.
June 2018: Jenner and Scott were seen front row at the Louis Vuitton menswear spring/summer show in France. Familiar faces including Woods, Kim, and Kanye flanked their sides.
July 2018: A pair of high-profile magazine covers featuring Jenner gained attention. After Jenner is featured on the controversial cover of Forbes, branded the youngest self-made billionaire ever, Scott tweets his support, writing, “CANT BE MORE PROUD,” alongside three hearts.
That same month, Scott and Jenner appeared together on the cover of GQ where insight about their relationship is revealed. Scott says the last time that he cried was when Stormi was born and Jenner admits that the two “rode off into the sunset” via his tour bus shortly after meeting. When asked about the public scrutiny on the pair’s relationship, Jenner had this to say to the outlet:
“I don’t think he’s really cool with it, but he deals with it, because we love each other and we have a family. For sure, I know he doesn’t like the attention. That’s why we just go the extra mile to keep our relationship super private, or like, if he has events or something, I won’t come. Because I want him to do his own thing. I want him to be him. I don’t want it to be Kylie and Trav. If people don’t ever see us together, that’s okay with me, because we just do our thing.”
Nearly 48 million people watched Jenner quiz Scott on everything from her eye color to the names of her dogs in a GQ video. Spoiler alert: he couldn’t quite remember Bambi.
August 2018: Jenner’s support of Scott’s music continued with her appearance in the music video for his song, “Stop Trying to Be God.” The businesswoman also posted about the release of Scott’s Astroworld album, wearing a shirt from the tour.
For Jenner’s 21st birthday, Scott went all out. Per People, he performed a set at Jenner’s all-pink event. Scott also showered Jenner with roses at her home, a trend he would be known to repeat. His official birthday IG for Jenner read: “happy bday wifey I love u mommy u my heart rib toes and all. May GOD continue to bless u and ur spirit. This mark in ur life is the start to more greatness.”
Scott and Jenner also made an awards show appearance together at the VMAs, where the rapper performed songs from his new album.
October 2018: Scott’s florally-inclined PDA continued—and this time causing rumors that him and Jenner are married. On October 15, Jenner posted a video of her walking into the house to find rose petals showered everywhere. She captioned the post, “just because flowers are the best kind??? thank u hubby.”
However, a People source dispelled rumors of wedding bells. “Kylie is very happy with Travis, but they aren’t married,” the source said. “There has been some talk about marriage, but it doesn’t seem they are planning a wedding.”
While the couple may not be husband and wife, a source tells Us Weekly that Scott and Jenner are “actively trying for another (baby).” Another major milestone this month? Jenner and Scott reportedly purchase a $13.45 million home in Beverly Hills, per TMZ.
Just in time for Halloween, Jenner posts snaps of her family at a pumpkin patch.
November 2018: Yes, even more roses seem to find a way to Jenner, courtesy of Scott. She shared a video of the surprise on November 6.
Jenner commemorated Scott’s first Astroworld Festival performance on Instagram, writing, “only the people around you really know how hard you work. i love to watch you make all your dreams come true. your first festival. we’re so proud of you. we love you ?.” She also made time to appear onstage during his concert at Madison Square Garden this month.
Jenner also posted a black-and-white family portrait on Thanksgiving, signaling the couple is doing great.
December 2018: However, rumors of cheating seem to find them soon after. A photo of a man resembling Scott with another woman hits the internet. But Scott shuts down the rumors on Instagram.
He appeared on the cover of Rolling Stone where he discussed the origins of his relationship with Jenner. He said in the beginning, “we was just two kids, fucking around. Maybe, like, the first week, you don’t know if it’s real or a fling. Then the second week you’re like, ‘Whoa, I’m still talking to her, she’s responding, I’m responding. We ain’t run out of a thing to say.’ And it got to a point where I was like, ‘I need her with me to operate. She’s that one.’
The musician also confirmed, “We’ll get married soon. I just gotta sturdy up—I gotta propose in a fire way.”
January 2019: Scott and Jenner put 2018—and rumors of infidelity—behind them for a vacay with Stormi.
Speculation about the couple’s marital status doesn’t bother Jenner too much. On January 22, she posts a photo of herself with the caption, “extraño a mi esposo,” which translates to “I miss my husband.”
February 2019: Stormi’s first birthday kicked off a major month for Jenner and Scott. Rumors loomed that Scott was planning on proposing to Jenner as part of his Super Bowl Halftime performance. Jenner documented Stormi’s reaction to Scott’s performance for Instagram. However, no public engagement happened.
On February 3, Jenner teased the possibility of her and Scott giving Stormi a little brother or sister. She posted a picture of the proud parents captioned, “baby #2?”
While the world is kept guessing about another baby, Jenner and Scott celebrate their firstborn with a lavish carnival-themed birthday party on February 10.
The festivities continued into Valentine’s Day, where Jenner posted Scott’s trademark elaborate rose display to Instagram. Two days later, the power couple attended the Grammy Awards.
In an interview for Paper magazine, Jenner finally (for now) put rumors to rest that her and Scott are married or even engaged. “I’ll let everybody know,” she promised when asked about when it’d happen.
March 2019: Despite the extravagant roses and trip to the Grammys the month before, split rumors strike again. After a TMZ report claimed Scott had cheated on Jenner, the artist deleted his Instagram and rescheduled a concert in Buffalo, New York. “Buffalo I’m so sorry I can’t perform tonight,” Scott tweeted. “I’m under the weather and it f*cking sucks! Can’t pull up without full rage. Show rescheduled to March 10 all tix are valid. See u soon.”
While TMZ said the cancellation came because of a fight with Jenner, Scott’s rep denied infidelity to People. By March 29, Scott was back on the ‘gram and posting a photo with Jenner.
April 2019: In typical fashion, Jenner and Scott jet away from breakup rumors. “baecation ??” Jenner captioned photos of the couple hugging in a pool.
They continued to show a united front on April 21, when Jenner posted a photo of the two at church. “tell me a secret bae #sundayservice,” she captioned the photo.
The day that Avengers: Endgame is released, Jenner and Scott posed in Marvel costumes. “oh you didn’t catch iron flame and captain lip kit in the credits? sucks 4 you,” Jenner wrote.
Jenner also shared a sweet post for Scott’s birthday on Instagram. She captioned a series of the couple’s photos, “watching you evolve into the partner, friend, son, and father you are today has been so fulfilling ♥️ my real life bestie & hubby all wrapped into one. i love you and I’m so so proud of you. happy happy birthday ?? let’s fuck around and have another baby. ?” Later that week, a gas station-themed birthday party is documented on social media.
As fans know, bigger is better with Scott and Jenner on holidays. So for good measure, Jenner rents out a billboard message for her boyfriend.
May 2019: In May, Jenner and Scott walked the Met Gala red carpet together. Other members of the Kardashian-Jenner family were also in attendance, including Kim, Kanye, Kendall, and Kris.
June 2019: Jenner wished Scott a Happy Father’s Day with a pair of black-and white father-daughter photos. She captioned the Instagram post, “Happy Father’s Day @travisscott ? I love the love you share with our daughter. ?? Thank you for all that you do.. today we celebrate you .. ?“
Video from Khloé Kardashian’s birthday party circulates where Jenner can allegedly be heard saying she’s pregnant. However, E! News confirmed that fans were mistaken. However, a source told the outlet, “Kylie talks about having another baby very frequently. She would love to have another baby with Travis and would love to be pregnant by next year. She talks about it all the time and feels like she was truly meant to be a mother.”
July 2019: In July, Jenner continued to share relationship moments with her 143 million Instagram followers. On July 21, she posted a photo of the two, writing, “partners in crime 4 evaaa??????.”
A few days later Jenner shared a sweet series of Stormi and Scott photos with the caption, “we took our baby on an adventure yesterday ???? ugh i love this little girl so much. not only do i think she‘s the cutest thing in the world.. she’s got the sweetest, smartest, most special little soul ?? p.s. the pat on the back at the end of the video gets me every time ?”
August 2019: Ahead of Jenner’s 22nd birthday, two recurring storylines return. First, Jenner posts footage of a lavish spread of roses from Scott to Instagram. Secondly, speculation about Jenner and Scott getting married during the birthday trip looms.
It all starts when Jenner was spotted heading to Italy for her $1.2 million-a-week yacht birthday extravaganza. Photos from TMZ show Jenner boarding her private jet with what looks to be a wedding dress. But a source told Entertainment Tonight, “She’s headed to Italy for her birthday. She’s definitely not getting married on this trip.”
What Jenner did do was share her travels on social media. “Perfect day in Positano ?” Jenner captioned photos of herself, Stormi and Scott.
Soon after, Jenner’s crew, which included Anastasia “Stassie” Karanikolaou, Sofia Richie, and Scott Disick, took the festivities to France. “Baby we should hit the South of France✨,” the birthday girl wrote alongside pics of her family.
Scott also gave Jenner a sweet shoutout for her birthday, writing, “Happy Bday Wifey everyday I watch u grow more into this amazing superhuman everyday is the best the day with u here may God continue shine on you. Happy fcking Bday love ya !!!”
The couple ended the month by showing PDA on the red carpet for his Netflix movie, Travis Scott: Look Mom I Can Fly.
September 2019: On September 10, Jenner teased a Playboy spread with Scott in an upcoming issue, writing, “When Houston meets LA .. ? @playboy #ComingSoon.” The rapper interviewed Jenner for the piece where she opened up about their connection. “We think the same, and we have the same goals and passions in life,” she said. “Besides the fact that we have good chemistry, we have a lot of fun together. You’re my best friend. Through all the ups and downs that every relationship has, we evolve together through them and keep getting stronger.”
However, a string of events shortly after raised some fans’ suspicions. On September 19, Jenner posted a selfie in her closet with the caption, “ain’t a game, boy ?????.” The semi-shady message and the fact that a framed photo of Scott previously in the background was gone, convinced some that they’d broken up.
Then, Jenner missed some engagements, including presenting at the Emmys alongside sisters Kim and Kendall, after being hospitalized with “severe flu-like symptoms.”
Jenner re-emerged at Hailey Baldwin and Justin Bieber’s South Carolina wedding in a revealing gold dress. Fans noted that the cosmetics mogul went solo to the event.
October 2019: Hours after the wedding, TMZ reported that Scott and Jenner were separated—for now. Sources explained that the couple had “been trying to make the relationship work for a while, but several weeks ago they decided to step away, at least for now.” However, they emphasized that the pair will “continue to co-parent and will keep Stormi as their number 1 priority.”
People and E! also confirmed the news, citing everything from trust issues to work stress as the cause of the split. An E! source claimed, “Kylie and Travis aren’t officially calling it quits on their relationship, but are taking space apart. It’s not a firm split. They’ve been fighting again, but have still seen each other within this last month. They fight over ridiculous things and Kylie can be very skeptical about Travis. Travis has been stressed with dropping new music.”
The night the breakup news broke, Jenner was spotted at LA’s Delilah with friends Stassie and Kelsey, followed by Sunset Marquis—the same evening ex Tyga was there. Per an E! source, the exes, who split in 2017, “have been in touch,” although “not often.” The source said,”It wasn’t an intentional jab at Travis, but she did hangout with Tyga for a bit. Nothing romantic is going on.”
Jenner addressed rumors of reconciliation with Tyga on Twitter the next day.
“The internet makes everything 100 times more dramatic than what it really is,” she wrote in her first tweet. “There was no ‘2am date with Tyga’. You see me drop two of my friends off at a studio that he happened to be at.” (Here, Jenner is refers to photos from the night, published by the Daily Mail.)
“Travis and i are on great terms and our main focus right now is Stormi,” she added with two exclamation mark emojis. “Our friendship and our daughter is priority.”
Next, it was Scott’s turn to speak on the split. “It’s really affecting when u see false things said about u,” he posted to his Instagram stories. “Once again these false stories about me cheating are just simply not true. Focusing on life, music, and family at this moment is what’s real.”
By mid-October talk of Tyga has cooled, and reconciliation rumors have returned. After Jenner made a brief appearance in Scott’s Instagram stories of Stormi, People, Entertainment Tonight, and E! each ran reports that the pair is just friends. However, getting back together remains an option.
Entertainment Tonight‘s source said, “Since Travis has some shows and is traveling, Kylie has Stormi more [often], but Travis is always in touch with her when he’s on the road.” The source added, “Kylie and Travis are both young, but they are very mature and have been handling parenting post breakup really well. Kylie and Travis don’t want any drama, and are on the same page of keeping Stormi happy.”
Meanwhile, the E! source said the couple had been growing closer,”They got along well and were so happy being a family with Stormi. It looked like nothing has changed with them.”
Jenner even posted a video of her playing Stormi a remix of her viral “Rise and Shine” moment, where Stormi instead asks for her dad’s music. “Daddy’s girl,” Jenner wrote alongside two eye roll emojis and a heart eyes emoji.
The end of the month brought a buzzed-about interaction between Jenner and Drake at his birthday party at Goya Studios. According to an Us Weekly source, Jenner “spent the most time near Drake and his friends,” at the party. “Kylie was rapping to songs and dancing with her friends while she was next to Drake, but they weren’t dancing together; they seemed to have a connection though.”
A second source added, “They seemed to be enjoying each other’s company. They were joking around, and Kylie was laughing. She seemed to be really happy and in a great mood and her and Drake seemed very comfortable with each other. There seemed to be an attraction there.”
November 2019: People reported that Jenner and Drake had been hanging out since his birthday. “He and Kylie have been spending time together recently,” a source said. “They’ve been friends for a long time and Drake is very close to the family.” A separate source described them as hanging out “romantically.” A third source disputed this and called the pair “just friends.”
Jenner and Drake reportedly spent time together at Kendall’s Halloween party, where E! reported that they left the party at the same time. “They went back and forth between the private bar area and the main area, and they were sitting together at points and hanging out all night. It looked flirty,” a source told the outlet. “At the end of the night Drake had a couple SUVs and he left at the same time as Kylie.”
A source told Us Weekly that “Travis harbors no ill will to any of Kylie’s friends,” which may or may not include her longtime friendship with Drake. Shortly after, Jenner flew to Houston to watch Scott’s Astroworld Fest performance, where she appeared to send him flowers. He posted a photo of them on his Instagram Story, writing, “Love u, That I really do.” A People source explained, “It was important for her to support Travis’ festival. They are still very close and often hang out with Stormi.”
On the Drake and Jenner front, her rep denied a source’s comment to People that “Kylie doesn’t seem to be dating. She sees Drake occasionally, but it doesn’t seem serious.” But an Us Weekly source said romance is still possible for the pair. “They have known each other and been friends for a very long time, and there has always been a spark there, but their situation is complicated and so is Kylie’s with Travis,” the source said.
“Drake and Kylie don’t want to jeopardize their friendship by crossing any major boundaries,” the source continued. “Drake doesn’t have any intention of taking on a fatherly role with Stormi, and he wants to have fun with Kylie with no strings attached and continue to have a friendship and be supportive of one another.”
Ahead of the holidays, an Us Weekly source claimed that although Scott “very much still loves” Jenner, he “feels that their relationship was too fast too soon. He loves her, but he wanted to be able to live his life and travel and be with other people and not have to worry about always going back to his family.”
For now, Scott and Jenner may be in breakup mode, but who can predict what 2020 will hold?