We're coming closer and closer to the end of Keeping Up With the Kardashians.
It's hard to believe the Kardashian-Jenner family have shared their lives with the public for the last 13 years. A lot has changed over that time. Their careers and appearances have transformed. Their life is a little less quirky these days and a little more fab.
Arguably, the biggest changes have come in the relationship department. We've seen many Kardashian-Jenner partners come and go since 2007. Some relationships were very under the radar, while others made headlines.
Recently, the LittleThings staff discussed which members of the family have had the best and worst dating histories. I also may have just ranted and they listened, but those are minor details.
I decided to do a deep dive into the dating history of each of the famous siblings. Year by year, here's who Kourtney, Kim, Khloé, Rob, Kendall, and Kylie have been connected with.
Pre-2007
While the Kardashians came into our homes in 2007, they were already semipublic figures. Because of the fame of patriarch Robert Kardashian and stepparent Caitlyn Jenner (formerly Bruce Jenner), the family always ran in affluent circles. As a result, we have an idea of what was going on in their lives before the show began.
Kourtney dated Taryll Jackson, son of Tito Jackson, from 2001 to 2004. She then was romantically linked to Girls Gone Wild's Joe Francis throughout 2005.
Kim had a Jackson relationship of her own, dating Taryll's brother TJ from 1995 to 1999. In 2000, she married music producer Damon Thomas. The pair divorced in 2004. Later that year, Kim began her infamous relationship with Ray J, only to call it quits two years later. In 2006, Kim was linked to Nick Lachey and Nick Cannon.
Khloé, then the most private of the three, didn't publicly date any notable figures prior to the show's premiere. Neither did Rob.
So who are the winners and losers here? Kim's definitely got the most interesting pre-KUWTK dating history, boasting both the best and worst pre-fame partner.
The best would be TJ Jackson. TJ's never had anything but nice things to say about his time with Kim, and the two remain friends to this day.
The worst, of course, is Ray J. Not just for leaking the sex tape — which many argue is the only reason Kim is famous — but for never, ever, ever passing on an opportunity to remind anyone the two were together.
2007 and 2008
In 2007, not only did KUWTK premiere, but so did some notable relationships in the family.
Kourtney began her roller-coaster romance with Scott Disick. If you've watched early episodes of the show, you'll remember the family wasn't on board with the relationship at first. Everyone's grown up quite a bit since the beginning, however, and now Scott is a member of the family regardless of his and Kourt's relationship status.
Kim began dating New Orleans Saints' running back Reggie Bush. Though his schedule often kept the two apart, he and Kim made an honest go of things for two years. Their video chats were a mainstay in the early show.
That year was also the beginning of Rob's relationship with former Cheetah Girl and current talk show host Adrienne Bailon. Their puppy love played out in the early seasons of the show.
All three relationships were featured on the show's first and second seasons.
Best: Adrienne Bailon. The beginning of Rob and Adrienne had all the makings of a sweet early 20s romance.
Worst: Scott. One of our earliest interactions with Scott is Kris trying to figure out whether he cheated on Kourtney, which we never technically got an answer to because she told Kris she was rude and to mind her business. Some things never change.
2009
Relationships were put to the test in 2009. Kourtney and Scott briefly split after she believed he cheated on her. They got back together when she discovered she was pregnant with their first child. Mason Dash Disick was born in December of that year.
Kim continued to work on her relationship with Reggie throughout 2009, but ultimately the couple split before the year's end.
Rob and Adrienne moved in together in 2009, upon which she discovered he was a slob. Though living together didn't seem to work, they continued dating for a bit before splitting up that year.
Khloé decided to step onto the dating scene. She briefly dated Rashad McCants, an NBA player who allegedly cheated on her months into their relationship. Rashad claims Khloé staged the relationship and the cheating and undermined his NBA career. Khloé claimed Rashad used her to try to find a space on the show similar to her siblings' significant others.
Fate had a little more in store for Khloé, however. Her whirlwind four-month-long relationship with Lamar Odom later that year resulted in the two tying the knot.
Best: Adrienne Bailon. She may have spent many years after this relationship lamenting her involvement, but at the time, she genuinely cared for Rob's happiness and well-being. He was clearly not ready for that serious of a relationship, but who is at 21?
Worst: Rashad McCants. Even if Khloé did everything he accused her of, the fact that he blamed an underwhelming NBA career on her is pitiful.
2010
Kourtney and Scott tried to navigate parenting while Kourtney tried to get Scott to face his addiction. Her threats to limit his time with Mason finally set him straight.
This was the year of the flirty fling for Kim Kardashian. She dated the Dallas Cowboys' Miles Austin. Their relationship was nice enough but fizzled out when their schedules got busy.
KUWTK fans may also remember this as the year that Kim had a fling with her bodyguard, Shengo Deane, which was documented on the show. While it seems they spent only a few fun days together, it showed a more relaxed side to Kim. Her year concluded with her starting her relationship with Kris Humphries.
Khloé and Lamar went strong throughout the first year of their marriage. They had their own spinoff show, perfume brand, and more.
Best: Shengo, honestly. Not many guys can say the news of their one-night stand with Kim Kardashian only got out because she chose for it to. No matter how many times he's been questioned since, he's been a gentleman.
Worst: Scott. His drinking problem got really ugly, and he refused to confront the issue, terrifying a lot of people in his path.
2011
Scott cleaned up his act and proposed to Kourtney, but she didn't know if she was ready for marriage, so she turned him down.
Kim's awful, short-lived marriage to Kris Humphries was also a product of 2011. The ugly crying memes will live on forever, but I have to pause and say that there were no winners in this situation. Kris would go on to join the legions of Kardashian-Jenner exes who cannot stop bringing them up.
Khloé started focusing on her professional life to prove once and for all that she was more than a basketball wife. On the outside, everything still looked great, but behind the scenes, their marriage was starting to see its troubles.
Rob also returned to the dating scene that year. His brief relationship with Rita Ora was a flame that burned and then burned out big. The two were happy together for a few months until Rob went on a massive Twitter rampage against the singer and accused her of cheating on him with over 20 different men.
Best: It's a tie between Lamar and Scott. Both were really sweet in their adoration of their ladies — and grateful to have them.
Worst: Kris Humphries. Again, even if Kim did scam him into a publicly embarrassing relationship, no one made him say rude and often misogynistic things to her on camera, knowing he was being filmed.
2012
This was the first year that saw every Kardashian-Jenner sibling romantically involved, folks!
In 2012, Kourtney and Scott's positive upswing led to the birth of their daughter, Penelope Scotland Disick.
Kim was guarded and embarrassed following her split from Kris Humphries. A man who long held a flame for her was just what she needed to feel secure again. Enter Mr. Kanye West. The longtime friends cross the line into something more, and it was super sweet to watch him sweep Kim off her feet.
Khloé and Lamar struggled through his time on the Mavericks before being traded back to Los Angeles, this time on the Clippers. Lamar also began to emotionally struggle, with both his career and his father's health. Khloé tried to be there for him, but a barrier between the couple was palpable for the first time.
Rob was spotted out with Rihanna several times over a two-month period, and he has been forever grateful that he gets to tell people that. She's maintained that he's fine.
Kendall and Kylie got their first boyfriends in 2012. Kendall dated Julian Brooks, while Kylie dated Cody Simpson.
Best: Scott Disick. This was a pretty good time between Kourtney and Scott, and it was nice to see the two settle into their family.
Worst: Lamar. You can truly feel for Khloé as their relationship falls apart throughout the show.
2013
This was a rocky year for most of the family.
In 2013, Kourtney and Scott continued to have ups and downs. The death of Scott's mom in November put him on a dark path.
Kim and Kanye announced that they were pregnant with their first child. Kim had a complicated and stressful pregnancy as she tried to finish her dragged-out divorce with Kris Humphries. That year was also Kim's first Met Gala with her infamous floral number. North West was born that June. The year ended on a true up note when Kanye proposed on Kim's birthday.
Khloé and Lamar continued to break down as his NBA career sputtered to a stop. Lamar was arrested for a DUI and did less than 24 hours in rehab. Just before the year's end, Khloé filed for divorce.
Rob dated Naza Jafarian throughout the year, but the relationship didn't go far.
Kendall was linked with Harry Styles for the first time in 2013 and would continue to be periodically for three years.
Kylie dated Jaden Smith throughout the year.
Best: Kanye. It was a sweet year for Kim and Kanye as they became parents and decided to get married.
Worst: Lamar. If you've ever endured a drawn-out end to a relationship that could've really been it, you can feel Khloé's pain.
2014
Kourtney and Scott continued to struggle in 2014. He lost his father just three months after his mother died, leaving him with few relatives. Kourtney revealed she was pregnant with their third child, but a depressed Scott returned to bad habits and reacted poorly. He spent some time in rehab before Reign was born that December.
Kim and Kanye got married in a beautiful wedding at the historic Forte di Belvedere in Florence, Italy, that spring.
Khloé found comfort in dating French Montana. Kendall was linked to Harry Styles, Justin Bieber, and Chris Brown. Kylie was also linked to Justin, as well as Miles Richie. The year ended with the beginning of her super-controversial relationship with Tyga.
Best: Kanye, but the competition wasn't particularly steep this year.
Worst: Tyga. They didn't go public until Kylie was 17, but they started talking when he was 22 and she was 14. Enough said.
2015
In 2015, Kourtney and Scott called it quits. Scott spent some time in rehab in Costa Rica while Kourtney was linked to — who else? — Justin Bieber.
Kim and Kanye welcomed their second child, son Saint West, that December.
Khloé dated NBA star James Harden on and off throughout the year. They reportedly split for good because he wasn't a fan of the media scrutiny of their relationship. That year, Lamar almost died of an overdose. Khloé was by his side, even calling off their divorce while he recovered.
Kendall was linked to Orlando Bloom, which was fine if you ignored that he's essentially a whole 18 years older than her.
Kylie continued to stay with Tyga, and no one really knew why. The year was spent in a lot of back-and-forth drama between her and his ex, Blac Chyna.
Best: Kanye, for stability if nothing else.
Worst: Pretty much everyone else.
2016
Scott and Kourtney briefly reunited in 2016, but it didn't last long. She also reportedly began seeing Younes Bendjima that year.
This year was hard on Kim and Kanye. Kim was robbed at gunpoint in France. As she struggled with her trauma, Kanye began struggling with his mental health, spending time in a hospital.
Khloé finalized her divorce from Lamar in 2016. That summer, Khloé started seeing Cleveland Cavaliers star Tristan Thompson.
Rob began seeing — drum roll, please — Blac Chyna! There was nothing weird about this, no matter how many times people pointed out that Rob and Kylie, siblings, could end up being stepparents to the same child.
Things got extra interesting when Rob and Chyna announced they were expecting their first child together. Dream Kardashian was born in November.
Kendall began dating A$AP Rocky in 2016, though the two kept their relationship very quiet.
Kylie and Tyga broke up and made up throughout the year.
Best: A$AP Rocky, by process of elimination.
Worst: Blac Chyna, mostly because nothing about any of this felt coincidental. However messy, this one didn't feel like a Kris Jenner creation.
2017
In 2017, Kourtney continued seeing Younes after it was clear Scott still had a lot to deal with. Things went well, with her publicly debuting the relationship around Halloween.
Kim and Kanye continued to recover from the previous year as they worked on growing their family. They announced they were expecting their third child via surrogate.
Khloé and Tristan had a great year, with everyone asking when wedding bells would ring. At the end of the year, they revealed they were expecting a baby girl.
Rob and Blac Chyna's relationship went from bad to worse to pure dumpster fire. There were accusations of abuse, leaked nudes, and a lot of bad behavior all around.
Kendall and A$AP Rocky parted ways. She began seeing Blake Griffin.
Kylie and Tyga finally called it quits. Kylie met Travis Scott at Coachella, and the two hit it off immediately. They quickly became inseparable. By the end of the year, pregnancy rumors swirled, but nobody confirmed anything.
Best: Tristan. Because we love a good love story, until it goes south.
Worst: Blac Chyna (and Rob for that matter).
2018
This was a year filled with good, bad, and ugly.
Kourtney was fine. She and Younes were rumored to be on and off throughout the year.
Kim and Kanye welcomed daughter Chicago West in January. Things were good until Kanye began to publicly spiral again. He was open about the fact that he thought his behavior was driving his family away. Kanye, who lives with bipolar disorder, would later open up more about his diagnosis.
Khloé suffered heartbreak just days before welcoming her daughter, True. Video of Tristan being unfaithful leaked publicly, and it became crystal clear he'd cheated on her while she was pregnant. True was born two days after the leak, and throughout the rest of the year, Khloé struggled with co-parenting with Tristan while still being angry and upset with him.
Kendall and Blake called things off. A few weeks later, she was spotted with NBA player Ben Simmons.
Kylie surprised a heavily spectating world with the news that she'd welcomed a baby girl in February.
Best: Travis Scott. Things definitely happened fast between Travis and Kylie, but their connection has always seemed pure, as has their dedication to their daughter.
Worst: Tristan. Never has a man seemed so unbothered by his reputation for cheating on pregnant women.
2019
Kourtney and Younes were on and off throughout the year. It never seemed to definitively end, as Kourtney became further and further withdrawn from the spotlight.
Kim and Kanye welcome their fourth child, Psalm, via surrogate in May. The couple also renewed their vows for their fifth wedding anniversary. Kanye had a spiritual awakening, and Kim continued working on her law degree and criminal justice goals.
Khloé took Tristan back, only to suffer a betrayal again. The two split after a rumored hookup between Tristan and Kylie's best friend, Jordyn Woods. Though she reined in her anger for True's first birthday, Khloé said she was done.
Kendall and Ben were reportedly on and off throughout the year.
Kylie and Travis had a wonderful year with baby Stormi but split up in October. Things stayed really amicable between the two, with all focus on their baby girl.
Best: Travis. Even in losing his partner status, he was an adult and never shady.
Worst: Tristan. Again. Always, probably.
2020 (So Far)
This year, Kourtney continues to lie low. Rumors of her and Scott reuniting will forever linger, but it seems like Younes is never too far from gone, either.
Kim and Kanye have struggled again this year, as he suffered another public mental health episode. They're committed to making their marriage work but continue to publicly clash on polarizing issues.
Khloé and Tristan are reportedly back together, although she's never quite confirmed it. The two decided to hunker down together when stay-at-home orders started, and things have been going well since. If the show's most recent episodes are any indication, her guard is still up.
Rob is reportedly opening himself up to dating again.
Kendall is reportedly dating Phoenix Suns guard Devin Booker.
Kylie and Travis are also rumored to be back together. They too have prioritized family during this unusual time.
It's too early, and arguably too strange a year, to call any winners and losers here. It's just more for us to keep up with in the months to come.