Sofia Richie and the Kardashian-Jenners Have Dated a Lot of the Same People

In the Keeping Up With the Kardashians world, relationship drama is expected. From cheating scandals to oversharing intimate details, this famous family is well known for its rocky road to love.

It’s probably not surprising, then, that some of that drama spills over into their friendships. The sisters and their friends have a tangled dating history. Sofia Richie is one friend who has crossed paths with the Kar-Jenner love life — maybe even more than people realize.

Sofia Richie and Kylie Jenner have been friends for a long time

Sofia Richie
Sofia Richie | Rodin Eckenroth/WireImage

Kylie Jenner and Richie have been close since childhood. With Jenner’s famous family and Richie’s famous father, it’s likely that they have traveled in the same circles quite a bit. By the time they were teens, the two spent a lot of time together at glittering events such as concerts, fashion shows, and parties.

When Richie started dating Jenner’s former brother-in-law, Scott Disick, it seemed as though the family distanced themselves a little. Jenner never said anything critical publicly, however.

The two may have been a little cool toward each other and more, but there was never any display of hostility. In fact, as the relationship between Disick and Richie went on, the friends started spending more time together

Of course, after three years together, now Richie and Disick have gone their separate ways. There are even rumors that he may be reuniting with Kourtney Kardashian, his ex and the mother of his three kids. Although that seems like it would be awkward, Jenner and Richie’s friendship looks as though it’s solid. 

Perhaps this stability between them is because the Kar-Jenners and Richie are accustomed to a joint messy romantic history. They’ve shared men before — more than once. 

Boyfriends in common

RELATED: Scott Disick’s Ex Sofia Richie Looks Suspiciously Similar to a Younger Kourtney Kardashian

An attentive fan on Reddit recently broke down the tangled love lives of Richie and the Kar-Jenners, and it’s complicated. 

Starting back in 2012, a very young Richie dated a very young Jaden Smith (they were both 14). After they broke up in 2013, according to Seventeen, Smith and Jenner started going out. Some people even think Smith was her first love, although it’s not clear how long they were together.

After Jenner and Smith broke up, she dated Richie’s brother Miles for a little while. 

In the fall of 2015, not long after she broke up with Disick, Kardashian dated Justin Bieber for a short time. The next year Richie dated Bieber. A foretaste of things to come, perhaps? Just a few years after that, Richie started dating Kardashian’s ex, Disick. 

Do these tangled relationships complicate friendships?

As mentioned before, the Kar-Jenners and Richie travel in a small social circle of the rich and famous. Because of that, it’s inevitable that they will date some of the same people along the way.

Friendships obviously won’t survive outright betrayal, such as the case with Jordyn Woods. She was once Jenner’s best friend, but when Woods was caught with Khloe’s boyfriend, Jenner cut her out of her life. But if friends happen to get together with the same people at different times along the way, it’s probably best for the Kar-Jenners to protect their friendships. 

Maybe it’s true, as one Reddit commenter mentioned, that Jenner isn’t as close to Richie anymore, because she, “realized it was weird being close with a girl that was dating her sister’s ex-boyfriend and father of 3 of her nephews and neices.”

But it seems as though the two longtime friends aren’t going to let this derail their friendship. Considering how small their circle is and how many romantic adventures they all have, this is probably a very wise choice.