Kylie Jenner: An In-Depth Analysis Of Why Her Relationship With Timothée Chalamet Makes Perfect Sense – And Why It Wouldn’t Have Happened Had She Not Been In The Toxic (And Abusive) Relationships With Tyga, Travis Scott, And Jordyn Woods

The world seemed to have been rejoiced after Kylie Jenner made her first red carpet debut with her boyfriend of two years, ‘Wonka’ actor, Timothée Chalamet, at the at the 70th David Di Donatello Awards, where the actor was set to receive the David for Cinematic Excellence honor. If you didn’t know, just as I didn’t know before I saw the news of them walking the red carpet together at the awards ceremony, the David di Donatello Awards primarily celebrate Italian films, but are the equivalent of the Academy Awards or the BAFTAs. The couple was rumoured to be broken up after Kylie attended the Met Gala solo earlier in the week, with Chalamet choosing to spend the day with his friends instead. This wasn’t the first time Kylie showed her support for her boyfriend. She also supported him during awards season this year, as well as the previous year. This, however, marked the first time the two walked the red carpet together.

It’s so nice to see them together, happy and at ease with one another. Kylie even publicly embraced a pimple – something she probably wouldn’t have done in the past. And speaking of the past, getting to write about Kim Kardashian’s life after leaving Kanye West made me think long and hard about Kylie’s own romantic past, starting from illegal relationship with rapper Tyga. The two started dating when he was 25 and Kylie was 16. They were together on-and off for 3 years, between 2014 and 2017, and their relationship faced significant scrutiny at the time due to their age difference. It’s really funny to me now because we somehow romanized Hilary Duff’s relationship with Joel Madden a decade prior when Duff was 16 and Madden was 25.

Kylie and Tyga first met in 2011 when Tyga was in a relationship with Blac Chyna (we’ll get to her later). Kylie was 14 at the time. The following year, Tyga welcomed a son, King, with Chyna, and the two got engaged shortly thereafter. Chyna was also friends with Kim at the time, and she even made an appearance on ‘Keeping Up With The Kardashians’. By 2014, Kylie was seen spending time with Tyga, and even celebrated her 17th birthday with him. Rumours of the two being together started to swirl, but Kris Jenner, Kylie’s mother, debunked these rumours. She told Ryan Secrest, who produced ‘Keeping Up With The Kardashians, ‘Kylie isn’t dating anybody. [Tyga is part of] this whole little group of kids who have been around forever – and I call them kids because relatively speaking, they kind of all travel as a pack and they enjoy each other’s company.’ The following year, however, Kylie posted a photo of herself with Tyga on Instagram with the caption, ‘Certain things catch your eye, but only few capture the heart.’ Ahh L’amour (I say sarcastically). Tyga even got a tattoo inspired by Kylie.

Kylie’s sister Khloe defended their relationship in an interview with Complex. She said, ‘Kylie is not a normal 17-year-old. ‘You’re not gonna say, ‘Hey, so what are you doing this weekend?’ and have her say, ‘Having a slumber party at my girlfriend’s’ or ‘Going to prom.’ That’s not what Kylie does. Kylie is taking business meetings and bought her first house, or she’s going on a private plane with Karl Lagerfeld to take a meeting. That’s not even what people do in their 30s. It’s a rare circumstance, so let’s treat this as a special case.’ (Hmmm…K) That same year, in 2015, Kylie appeared in Tyga’s R-rated music video for ‘Stimulated’, with lyrics that read, ‘They say she young, I should’ve waited / She a big girl, dog, when she stimulated.’

After breaking up at least twice, with reasons including cheating on Tyga’s part, the two finally parted ways for good in April 2017. The two reportedly stayed friends and were even seen publicly spending time together a few times following their split. A source told People in 2019, ‘There is a lot of history and they both care for each other deeply. She has a soft spot for him and vice versa.’ To that I just say, ‘Well, DUUH….’ This was her first boyfriend in her teen years, and he took advantage of her in their power dynamic. Of course she’ll have a soft spot for him.

Correction, though. Tyga wasn’t actually Kylie’s first boyfriend. Beforehand, she dated Cody Simpson, who also previously dated Miley Cyrus, as well as Jaden Smith, who is Will Smith’s son with Jada Pinkett-Smith, another odd couple. During an August 2017 episofe of episode of ‘Life Of Kylie’, Kylie opened up about the breakup with Tyga in her own words. She said, ‘There was absolutely not one thing wrong with me and T. He and I will always, always have a bond. There was no crazy fight, we just decided … Well, I decided that I’m really young. I don’t want to look back in five years from now and feel like he took something from me when he’s really not that type of person.’

I found this so hilarious, because on the one hand, she said she was too young, but on the other, practically immediately after her breakup with Tyga, she got together with Travis Scott, and then almost immediately got pregnant with her daughter, Stormi. Rumours first began to swirl that the two were together after they were seen holding hands at Coachella 2017 that April. By September, it was confirmed that the then-20-year-old was pregnant. In a YouTube video posted on Feb. 4, 2018, the couple announced that they had welcomed their daughter. In 2019, Kylie told Playboy magazine, ‘You can be sexy and still be a badass mom.’ And the rapper added, ‘A lot of people claim that having a baby can hurt your sex life, but I feel like that’s the opposite of our experience.’

That same year, Tristian Thompson had his second cheating scandal unfold. This time, Kylie’s best friend and frequent collaborator, Jordyn Woods, was involved. They kissed and she sat on his lap. The following day, Jordyn had Kylie post photos of the two of them, knowing what she did, hours before news of what had happened broke. Kylie, of course, in a very Kardashian manner, showed her loyalty and took her sister’s side. She had Jordyn move out of her house immediately and unstitched a collaborative makeup kit for Kylie’s brand, Cosmetics. At this time, 6 years later, Kylie is still friends with Jordyn, but they certainly keep a distance between them, and there’s no co-dependency in their relationship. Later that year, in October 2019, Kylie and Scott broke things off. During their off period, Kylie had a fling with Drake. You know, the one who played Jimmy Brooks on ‘Degrassi: The Next Generation’ for the first 7 seasons of the show. By summer 2021, she and Scott were back together and expecting their second child. Their son, Aire, was born in February 2022. Less than a year later, they broke up again.

In April 2023, rumours started to swirl that Kylie was romantically linked to Timothée Chalamet. They were spotted together numerous times by TMZ. Sources told People at the time, ‘It’s not serious. Kylie is having fun. After years of back and forth with Travis [Scott], she just wants to date without any pressure.’ The sources also revealed that the Kardashian-Jenner family was supportive of Kylie’s new relationship. Two months later, Scott reportedly dissed Kylie’s new boyfriend in his song, ‘Meltdown’. Lyrics for the song include, ‘Chocolate AP and chocolate the Vs (Vs), got the Willy Wonka factory (Vs) / Burn a athlete like it’s calories, find another flame hot as me, bitch.’ An ‘AP’ refers to the Audemars Piguet watch and diamonds, while the Willy Wonda factory may be a jab at the actor. Timothée stars as Willy Wonka in the actor’s ‘Wonka’ role.

The actor had reportedly met Kylie’s family, though he never made an appearance on their Hulu reality show, ‘The Kardashians’ in the 2+ years that they’ve been together. In October 2024, a source told People magazine, ‘He’s close with her family and she’s close with his family. It’s very serious, but also a fun relationship. They’ve really been able to figure out a good balance between working and spending quality time together.’ Obviously, this was a much different account of their relationship that sources had at the very beginning of their union. Though the two have been seen spending time together periodically in the past two years, this is the most private that Kylie’s ever been since the beginnings of ‘Keeping Up With The Kardashians’ in 2007. I remember when news of their relationship were first reported, I thought it was all just some sick joke. Like, what would a serious actor that’s Timothée Chalamet, who starred in movies such as ‘Call Me By Your Name’, ‘A Complete Unknown’, ‘Don’t Look Up’, ‘Dune’, and many more greats, ever want to do with a reality star. I was also THAT judgemental B*tch who agreed with internet trolls that they looked like an older mom kissing her teenage son (Yieks!).

Over time, however, once some time to adjust to their relationship (Yes, I realize I’m speaking of them as if I know them and am close to them when I’m actually SO not), I realized I was absolutely, astoundingly wrong. In actuality, Kylie’s relationship with Timothée Chalamet was exactly what she needed, and they make perfect sense. In hindsight, he’s brought the best, healthiest in her in the past couples of years, and it’s the happiest, healthiest, and I’d even say most natural that we’ve ever seen Kylie be in the past decade or so. I’m going to exclude Kylie’s relationships with Cody Simpson and Jaden Smith here, because they mostly, at least in my eyes, teen crushes that were by no means ever meant to last. She was also in a relationship with Tyga when she was a teen, but this one’s important, because it brings up a bigger issue than just a teenage girl being in her first serious relationship.

Let me be clear that a 25 year old grown man dating a 16 year old teenage girl ISN’T normal at all. It’s grooming. By its mere definition, grooming is ‘the action of attempting to form a relationship with a child or young person, with the intention of sexually assaulting them or inducing them to commit an illegal act such as selling drugs or joining a terrorist organization’. Sounds intense, right? That’s because it is. You might ask yourself how Kris Jenner, Caitlyn Jenner (then Bruce Jenner) allowed this to ever happen. I did too. But then I looked back at the family’s history. Kim married Damon Thomas, a producer 10 years older than her, when she was just 19 years old. It would’ve been completely normal for them to be married now, but back then? Absolutely NOT. Khloe was also having wild nights when she was a 14 year old girl. She also lived with The Game when she was underage, about 16 or 17 years old, and he publicly bragged about having slept with her, Kim, and Blac Chyna. Kris herself met Robert Kardashian when she was underage. He was born in 1944, and Kris was born in 1955.

It’s safe to say that the family didn’t know any better, as to them, this was a normal relationship dynamic between two people – a man and a woman…(Urgh) I mean a teenage girl. No matter the case, however, even in the case of this not being a normal relationship dynamic between two people romantically involved, there was absolutely nothing the family could’ve done. Tyga was a man that had enough money to get himself out of jail and woo himself back into Kylie’s life, and he would’ve been more than happy to turn Kylie against her own family had not been there to support her and her relationship with him.

In 2021, well after his breakup with Kylie, Tyga was arrested on domestic violence charges for hitting his ex-girlfriend, Camaryn Swanson. On her Instagram Stories at the time, Swanson shared photos and videos in which she has a large bruise near her eye, while she also showed a cuff of her sweatshirt, which appeared to have a bloodstain on it. Accompanying those two posts, Swanson wrote, I’ve been emotionally, mentally, and physically abused and I’m not hiding it anymore. I’m so embarrassed and ashamed it had to get to this but I have to stand up for myself.’ In 2011, Tyga was involved in several lawsuits, including one that involved his music video for ‘Make It Nasty’. Three women were told there would be no nudity in the video, but on set they were asked to appear topless, and promises that their exposed breasts would be edited out were allegedly not met. Soon after, another woman alleged that, during the shoot, she was given alcohol, forced to appear topless on camera, and groped by someone in a rabbit suit. 

It’s absolutely disgusting. Abuse is rarely a one-off event, and domestic abuse behaviour tends to get worse over time. That was exactly why no one believed Amber Heard when she accused her ex-husband, Johnny Depp, of domestic violence. None of his exes had anything negative to say of his respective treatment towards them. They all said under oath that there was absolutely no signs of ANY abuse throughout their respective relationships. The same couldn’t be said about Tyga. And maybe I’m saying this because I know the signs of abuse as I’d experienced abuse myself as an IPV (Intimate Partner Violence) survivor, but I saw the signs even in the few scenes I’ve seen of Tyga when he appeared on ‘Keeping Up With The Kardashians’. Like when Kylie brought him to a family vacation and she cooked a meal for him and cared like a nurturing wife, he showed no emotion whatsoever; or when Kylie brought him as her plus one to a club with the family, and he suddenly told her they were leaving to go to another club and she followed him like a mulled even though Khloe came to the club shortly beforehand and only came for her. Kylie was a kid and couldn’t the situation and what was actually going on.

And now it’s time to talk about Travis Scott. The age difference between the two is 6 years, but it’s also important to factor in that they first got together when Kylie wasn’t even 20, and Scott was 26. It wasn’t even 2 months into their relationship that Kylie got pregnant with Stormy (based on the math of how reproduction works). It seemed as though the only thing that was keeping them together was the baby. It was even rumoured at the time that Kylie was only with Scott because she was trying to make Tyga jealous. It’s obviously not a good reason to get into a relationship with someone.

Nevertheless, the two stayed together, at least for the sake of the new baby. Although, to be honest, it seemed as though Kylie was more in a relationship with Jordyn Woods than she was with Scott. There was a co-dependency there between the two friends that was just unhealthy. But she never failed to post her boyfriend’s grand gestures, including one for her 22nd birthday in August 2019, and just two months later, they broke up due to cheating allegations. But not before she, herself made a grand gesture for HIS birthday that April. Their relationship seemed to have been heavily defined by them, and it’s problematic because grand gestures in relationships can be toxic when used as a manipulative tactic, often seen in love bombing’, a form of affection that aims to gain control. While grand gestures can initially feel exciting, they can mask an underlying lack of genuine connection and be used to control and isolate a partner. To look at it in a more detailed look:

1. Love Bombing and Control: 

• Initial Stage: Grand gestures, like extravagant gifts or constant attention, are often used early in a relationship to overwhelm and “love bomb” a partner, creating a sense of intense infatuation. 
• Manipulation: This behavior is often employed by individuals seeking to gain control and influence over the other person. 
• Red Flags: Excessive compliments, constant attention, and declarations of love too soon can be warning signs of a manipulative dynamic. 

2. Grand Gestures as a Fix: 

• Addressing Past Behavior: A grand gesture might be presented as a solution after someone has hurt or disappointed their partner. 
• Manipulation to Shift Focus: Instead of acknowledging and addressing the issue, the grand gesture is used to distract from the problem and potentially shift the blame. 
• Emotional Manipulation: The gesture might be designed to make the partner feel obligated or indebted, potentially reinforcing unhealthy patterns. 

3. The Dark Side of “Grand Gestures”: 

• Narcissistic Tactics: Grand gestures can be a hallmark of narcissistic behavior, where the individual uses them to inflate their own ego and gain admiration. 
• Emotional Abuse: In some cases, grand gestures can be part of a larger pattern of emotional abuse, where the partner is manipulated and controlled through displays of affection. 
• Genuine vs. Manipulative: It’s crucial to distinguish between genuine gestures of affection and those that are used as a manipulation tactic. 

4. Red Flags to Watch Out For: 

• Exaggerated Displays of Affection: Over-the-top gestures that don’t align with the nature of the relationship. 
• Isolation from Friends and Family: The partner is pressured to cut ties with loved ones. 
• Lack of Genuine Communication: The focus is on grand gestures rather than open and honest communication. 
• Control and Domination: The partner is controlled through guilt, threats, or intimidation. 

5. Healthy Relationships: 

• Mutual Respect: Healthy relationships are built on mutual respect, understanding, and genuine connection. 
• Open Communication: Partners communicate openly and honestly, addressing issues constructively. 
• Authenticity: Actions and words are aligned, reflecting genuine feelings and intentions. 
• Boundaries: Healthy relationships prioritize boundaries and respect for each other’s needs

There was practically nothing healthy about Kylie’s relationship with the father of her child. I think she most definitely loved him, but he didn’t love her. I don’t think he liked her. I don’t even think he knew anything about her. Their joint GQ interview from 6 years ago was awkward as F*CK. They were always meant to be a fling, but their daughter kept them together. I honestly believe that if it wasn’t for their daughter, they wouldn’t have lasted even 6 months, and we l, the people from the outside looking in, probably wouldn’t have even known that they were even a thing.

Weeks before their 2019 breakup, Kylie and Scott appeared on the cover of Playboy where they interview one another. The shoot itself was directed by Scott.Kylie said of their relationship, ‘We think the same and have the same goals and passions in life. 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.’ When Scott said, ‘A lot of people claim that having a baby can hurt your sex life, but I feel like that’s the opposite of our experience,’ Kylie responded, ‘Yeah, I feel like we’ve definitely proven that rumour to be wrong. You remind me that motherhood and sexuality can coexist, and just because you embrace your sexuality doesn’t mean you have loose morals or you’re not a good mother. You can be sexy and still be a badass mom.’ Kylie also revealed how much fun they had in their downtime. She said, ‘When we have our days off, we play with Stormi all day, and the three of us have a lot of fun together. We do a lot of swimming; Stormi loves swimming, so we’re always in the pool or playing in her room or taking her out to lunch with us. We have a lot of fun together. We’re always laughing or getting into deep talks.’

And each time she was asked about Scott, Kylie’s face even lit up during her interview on ‘The Ellen DeGeneres Show’ just two days before the GQ cover was released; particularly when asked about what her favourite thing about him was, and what he smelled like. She obviously loved him more than he loved her. Or maybe he just had trouble showing his love for Kylie. But despite this, he had absolutely no issue whatsoever in showing his love and devotion for his daughter. His face completely changed whenever he looked at her. His role as a father was crystal clear. In the year and a half that they were apart, Kylie and Scott remained co-parents. Eventually, by 2021, they got back together, and very soon after, just like last time, Kylie became pregnant yet again.

It seemed as though each time they got together, the very beginnings of their union resulted in a pregnancy. Their son Aire was born on February 2, 2022, just a day after Stormi’s 4th birthday. Just as she did when Stormi was born, Kylie released a video on YouTube chronicling her pregnancy with her son. It showed clips from her baby shower, which included Scott and his family, particularly his mom. In the video, his mom said that she saw a different person in her son since Stormi was born, and that she was glad that Kylie was the mother of her grandchildren. Her speech was absolutely beautiful. It was everything that a woman wants to hear from a mother-in-law when she becomes a mom. I’m lucky enough to have heard it myself from my own mother-in-law. But especially, when she hears someone question my capabilities in taking care of my son, she immediately interrupts them and says, ‘She can do anything we do with two hands, and better.’

Some men are meant to be fathers, but not partners. Some men are amazing fathers, but sh*t partners, and I think this was exactly the case with Travis Scott. Since their 2023 breakup, he and Kylie have been great at co-parenting. It’s been reported that the former couple are on good terms and prioritize their friendship as they co-parent, with the intent to prioritize the well-being of their two children. Stormi and Aire now split their time between Kylie’s home in California and Travis’s in Texas. When Kylie travels, the children usually stay with Scott, and when Travis is out, they stay with Kylie. If both parents are traveling, the children often join Khloe Kardashian and other family members. It was actually Scott’s Astroworld Festival tragedy, where ten people died, that led to them being more connected with one another as parents. It was November 2021, before Aire’s birth, and they were reportedly already separated at the time. And during Coachella this year, Kylie attended the event with her current boyfriend, Timothée Chalamet while Scott performed. Their daughter was there too to support her father. Kris Jenner was also there to spend time with the family.

I think Khloe Kardashian said it best when talking about her ex, Tristian Thompson, who cheated on her VERY publicly 3 times throughout their relationship, and her current relationship with him as co-parents. She said on the ‘She MD’ podcast that they weren’t meant to be together, but he was meant to be the father of her children. I think this also perfectly describes Kylie’s relationship with the father of her children. They weren’t meant to be together, but he was meant to be the father of her children. Kylie wasn’t meant to be with Tyga either, and thankfully, she doesn’t have kids with him, and therefore, doesn’t have to be associated with him in any shape or form whatsoever. He’s not a good partner. He’s (probably) not a good father to his son with Blac Chyna. And he’s not a good person all in all; not someone anyone would want to have any association with.

I believe that Kylie most certainly was meant to be with Timothée Chalamet. What she has with him is REAL LOVE. But she wouldn’t have been able to appreciate the relationship to its fullest had she not been in relationships with sh*tty partners in the past. It’s the same with me. I wouldn’t have been able to appreciate my husband the healthy, loving, and loyal relationship that I share with him had I not been through such turmoil in my personal life before him. Thanks to my own past, Im able to correlate the good from the bad. My husband is an amazing partner and an amazing father to our son, but had I not been through trauma and abuse in the past at the hands of my former boyfriends and the person that raped me, I would’ve concentrated too much on his flaws rather than focus on everything that’s good in him, everything he’s done for me and our family, and everything he’s given up to be with me. We’ve recently gone through a tough period in our relationship, and my mom sat me down one day and told me I’d be stupid to let such a good man go.

My mom was 100% right, because no matter how hard things might get between my husband and I, I know that what I have with him is a once in a lifetime type of love. As weird as it might sound, I’m actually so grateful for the trauma I’d endured in the past, because had it not happened to me, I wouldn’t be where I am today – married to a man that’s actually good to me. My sexual trauma affected my relationship with him, no doubt, throughout the years. But it also forced me to sit and reflect time and time again on everything that I’ve gained on the other side – in spite of it. And it’s actually more than just about the safety that I’ve felt in my relationship following my trauma, but my life as a whole. Like….just to be able to be home alone, be in my own thoughts while I’m having a cup of coffee, and feel safe while doing it is…so liberating. And I know it may sound so small and so stupid, but it’s really just about the little things. Such big traumatic events that happen in your life make you appreciate the little things that make you happy. It’s the perfect storm.