Kylie Jenner started dating when she was barely 12 years old, and her first known boyfriend was singer Ramsey IV. Since then, she had several boys and men come in her life and has always been in the news. After all, she is a Kardashian! Already a mother at age 20, rapper Travis Scott is Kylie Jenner’s baby daddy and current beau!
Anything that the Kardashian clan does is big news. Even lil’ sister Kylie Jenner makes headlines!
Even though she is the youngest of the famous sisters and only 20 years old, the list of Kylie Jenner’s boyfriends over the years is quite long. Starting from her first boyfriend, singer Ramsey IV, to her current beau and baby daddy, rapper Travis Scott, Kylie has been in the headlines for her numerous hookups.
Kylie seems to have a penchant for musicians as most of her boyfriends (both rumored and real) have been rappers or singers. And boy has she made sweet music with them over the years, especially with her long-standing former boyfriend, Tyga.
Check out Kylie Jenner’s dating timeline and list of her boyfriends below!
Kylie Jenner’s Dating History:
- Travis Scott – Rapper (2017 – Present)
- Tyga – Rapper (2014 – 2017)
- PartyNextDoor – Rapper (2016 – Rumor)
- A$AP Rocky – Rapper (2015 – Rumored Fling)
- Stitches – Rapper (2015 – Alleged Affair)
- InkMonstarr – Rapper (2015 – Alleged Affair)
- Justin Bieber – Singer (2014 – Rumor)
- Miles Richie (2014)
- Jaden Smith – Actor (2013)
- Cody Simpson – Singer (2012)
Travis Scott, Baby Daddy & Her Current Boyfriend
Timeline: 2017 – Present
Travis Scott is not only Kylie Jenner’s current boyfriend, but he’s also the father of her first child. That’s right!
Kylie gave birth to their baby girl on February 1, 2018, and the couple has lovingly named her Stormi Webster. But how did Kylie Jenner and Scott meet in the first place?
For that, Kylie has to thank her older sister, Kendall Jenner, because she has been friends with the rapper since 2015 and often hung out with him. Scott even performed at Kendall’s 21st birthday party in November 2016. And since Kylie and Kendall are very close, it was easy for Kylie to talk to the rapper.
Their friendship soon turned to romance, and the relationship has been further cemented by the baby coming into their lives. Now, Kylie is looking forward to a full life with Scott and their baby girl, Stormi, with her past firmly behind her.
Tyga, On-Again Off-Again Lover Boy
Timeline: 2014 – 2017
You can’t find a better example of an on-again-off-again relationship than the one between Kylie and Tyga. He is an American hip hop singer who had a controversial relationship with Kylie that saw many ups and downs during the three years they were together.
Can you guess how Kylie and Tyga first met?
Well, Kylie has her older sister Kendall to thank for that once again! When Kendall held a party to celebrate her Sweet 16 in 2011, Tyga was the entertainer for the evening.
Kylie, who was just 14 years old at that time, danced with abandon as Tyga turned on the heat with his energetic performances that evening. They became friends and started dating when Kylie turned 16 years old.
Tyga and Kylie spent a lot of time together and went on many vacations, giving more than enough fuel to the paparazzi. Their split came suddenly and as a shock to their fans, who wondered what went wrong between the two.
While some said that it was due to finances, others said that Kylie got bored with their relationship and was upset that Tyga hadn’t given her a ring. But what did Kylie have to say about their split?
Kylie said that she did not fight with Tyga but wanted to experience other things.
She felt that she was “too young” to be in a serious relationship. So, she ended their three-year on-and-off relationship for good.
PartyNextDoor, Rumored Ex-Boyfriend
Kylie Jenner appeared in the music video of PartyNextDoor’s song, “Come and See Me,” in 2016. Later, there were rumors that she and the Canadian rapper were dating and were an item.
However, Kylie confirmed later in an interview that while they were not boyfriend and girlfriend, they did have fun together. Mind you, all this happened when Tyga was allegedly still around.
A$AP Rocky, Rumored Fling
Kylie was rumored to have hooked up with the American rapper in 2015. But neither party has spoken about it.
Even though he is nine years older than her, it is believed that Kylie had a brief fling with him.
Stitches, Big Mouth & Alleged Affair
Stitches is an American rapper with several albums like I Need Rehab and Bipolar to his credit. He also had his “15 minutes of fame” when he claimed that he had “done everything” with Kylie Jenner.
Allegedly, this occurred just a few weeks after her 18th birthday in 2015, when she was still dating Tyga. But Kylie did not confirm anything regarding this matter, so the jury is still out on this one.
InkMonstarr, Hooking Up & Alleged Affair
In 2015, the rapper claimed in a diss video aimed at then-boyfriend Tyga that he had hooked up with Kylie Jenner. Again, it’s a claim that is not backed by any proof.
Could it be that guys are using the youngest Jenner to get famous by making headlines?
Justin Bieber, Good Friend & Rumored Ex-Boyfriend
After Justin Bieber’s break-up with Selena Gomez in 2014, there were rumors of him and Kylie dating. It was all over the tabloids back then, but neither of them commented on their relationship.
They are believed to be good friends even today. But they have never said anything about their friendship ever turning romantic.
Miles Richie, Tattoo Lover & Getting Cozy
Kylie Jenner dated Miles Richie, the son of legendary singer Lionel Richie, for a while in 2014. They were kids at that time, with Kylie being just 16 and Miles being 18 years old.
Miles even got her initials tattooed on his hand. And the couple was spotted getting cozy in Los Angeles several times.
Once Miles was about to kiss Kylie in his car, but she turned away at the last moment when she spotted the dreaded paparazzi.
Jaden Smith, Younger in Age & Puppy Love
In 2013, Kylie was in a relationship with Jaden Smith, the son of Hollywood stars Will Smith and Jada Pinkett Smith. He made his acting debut in the acclaimed movie, The Pursuit of Happiness.
It was a classic case of puppy love. And for once, Kylie was the older partner in the relationship.
Back then, Jaden had described his relationship with Kylie as “pretty awesome” and had declared the then 15-year-old to be “one of my best friends.” Those were the exciting days of young teenage love when it seemed that nothing could ever go wrong.
But things did go wrong, and it was rumored that the couple had several fights. Kylie even shared her feelings about them on social media.
In the end, the duo decided to move on and be good friends.
Cody Simpson, Ex-Boyfriend & Joking Along
Timeline: 2011 – 2012
Before Jaden, there was Cody Simpson, an Australian singer, songwriter, actor, and dancer. All seemed well, but they later broke up.
Neither said much about their relationship when they were together. But Simpson sure joked about their breakup on television.
On a talk show called Hello Ross, Simpson joked that the relationship fizzled out because of the letter “K.” He said that he could have changed the spelling of Cody but “the whole K-O-D-Y thing didn’t really work for me.”
The couple didn’t really talk about their relationship while it was ongoing or even after it broke down.
Ramsey IV, First Lover Kid
Timeline: 2008 – 2011
Ramsey IV was the first boy in Kylie’s life. She was just 12 years old when love blossomed between the two.
The singer dated Kylie for a few years. And there are several photos of the pair where the flush of first love is clearly visible.
It’s been almost 10 years since the pair hooked up. But it feels like it was so long ago until you realize that Jenner is still just 20 years old. And a mother to boot!
Finally Finding Happiness
So, the last 10 years of Kylie’s love life have been action packed with several guys figuring in it. Some have claimed to be her fling while some were rumored to be her boyfriend. And a couple of them really were, and she has acknowledged it.
Kylie seems to have found bliss with rapper Travis Scott and her baby daughter Stormi Webster. The past is over, and now Kylie Jenner is looking forward to a rewarding and fulfilling future as a young woman and mother!