Makeups, Breakups & Babies: A Timeline of Tristan Thompson's Love Life

In the wake of a cheating scandal, Khloé Kardashian finally put an end to her tumultuous relationship with boyfriend Tristan Thompson.

A source told PEOPLE that Kardashian and Thompson “are 100 percent over” after reports surfaced that Thompson, 27, cheated over the weekend following Valentine’s Day with Kardashian’s sister Kylie Jenner‘s longtime best friend, model Jordyn Woods, 21. In a Red Table Talk interview on March 1, Woods told host Jada Pinkett Smith that Thompson kissed her as she left an afterparty at his home — but nothing more ever happened.

This isn’t the first — or the second — time that the Cleveland Cavaliers player has been accused of getting too close to other women while in a relationship. In case you haven’t been keeping up with his and Kardashian’s complicated history, we’ve broken down a timeline of his love life, from his early romance with his college sweetheart to the public scandals that have undermined his relationship with the Good American founder.

2011: His college romance

While the athlete wasn’t widely known outside the sports realm until his budding relationship with Kardashian started making headlines in September 2016, E! News reported that he was profiled in an article by Sportsnet Magazine that gave some insight into his life at the time after he was picked fourth overall in the 2011 NBA draft.

According to the outlet, the lockout that followed prompted him to return to school at the University of Texas full-time, where his biggest expense was a “furnished, off-campus apartment he shares with his girlfriend, Whitney, who graduated from UT in the spring and works for a recruitment company in Austin.”

2014: He and ex Jordan Craig go to Paris

Thompson started dating social media influencer and entrepreneur Jordan Craig in 2014. The two jetted off on a romantic trip to Paris that August, and while they didn’t post photos together, they each documented their time in the City of Love with solo shots of themselves — that appear to be taken by each other — on their respective accounts. Posing in front of the castle at Disneyland Paris, Thompson captioned an Instagram post, “Times like this, I go back to being that little kid from the 6…” Craig shared a similar shot of herself in the same spot.

2015: He and Jordan go to Jamaica

The pair also took a tropical getaway for Valentine’s Day in 2015, where they took a private plane to a luxury hotel in Jamaica and again shared solo snaps of themselves posing against the same picture-perfect backdrops. Craig posted a photo of herself looking out at the sea view from a bubble bath, and simply captioned it, “#VdayView,” along with a pink heart emoji.

According to their Instagram photos, they returned to Jamaica a few months later for the 4th of July as well.

2016: He and Jordan welcome a son — and he’s spotted with Khloé Kardashian while Jordan is pregnant

The last trip the pair posted about was another getaway to Jamaica to celebrate Valentine’s Day in 2016. Craig later publicly revealed she was pregnant with Thompson’s son, Prince Oliver (whom she welcomed that Dec. 12), when she shared photos and videos from her baby shower in October 2016 — one month after Thompson and Kardashian were first linked.

The athlete and the reality TV personality were spotted on a Labor Day weekend getaway to Cabo San Lucas, Mexico, and a source revealed to PEOPLE at the time that they had “been seeing each other for a little bit.” The source added, “It’s unclear for now if it’s going to turn [into] anything super serious, but for now they’re having a good time together.”

Rumors began to circulate that Thompson left Craig while she was pregnant, though neither he nor Craig confirmed if he met Kardashian while still in a relationship. Kardashian later denied it in an Instagram comment after a fan wrote, “He left his pregnant girlfriend to be with you and you think he won’t leave you someday” on a since-deleted clip she’d posted.

“PS he never left ANYONE for me,” she clarified. “I have said this before but as I have learned the truth isn’t as exciting as a lie. So the lie is what gets traction. The truth seems to get buried and ignored. Either way, it’s all love and peace over here.”

2016: His relationship with Khloé takes off

Things quickly heated up between the pair, who were set up by a mutual friend. In the months that followed their Mexican vacation, Kardashian spent much of her time with the Cleveland Cavaliers player, regularly flying out to support him and even flaunting his NBA championship ring on social media. “She’s very supportive of him, and they’re getting serious,” a source told PEOPLE in October 2016. “They really dig each other a lot.”

The pair went all-out with their couples costume that Halloween, dressing up as Marvel comic characters Storm and Black Panther. Thompson documented their looks on Instagram, sharing an intimate photo of them standing close together and staring at each other (although he had a mask on).

On Christmas, the Ontario native shared another photo of the pair posing in coordinated fur coats, writing, “Merry Christmas & Happy Holidays from me and mines, to you and yours.”

2017: He and Khloé get serious — and later reveal they’re expecting

As their relationship progressed, Kardashian felt ready to take the next step with Thompson. She revealed on Keeping Up with the Kardashians in June 2017 that she had stopped taking birth control. “Tristan and I definitely talk about starting a family,” she said. “He wants to have about five or six kids with me and that’s lovely. We could start at one and we could grow from there.” Later that month, a source told PEOPLE that Kardashian is “very happy and positive” about her future with Thompson. “She is absolutely hoping for an engagement,” added the insider.

In September 2017, multiple sources confirmed to PEOPLE that Kardashian and Thompson were expecting a baby together. Kardashian waited to publicly confirm the news herself until Dec. 20, one week after Thompson’s son Prince was born.

2018: Tristan is seen getting close to another woman — just days before Khloé’s due date

In April 2018, just a few days before Kardashian was due to welcome their daughter True, photos and videos surfaced of Thompson getting too close to a girl at a bar in Manhattan. Another video captured him entering a hotel with that same girl at 5 a.m., which prompted allegations that he was cheating on Kardashian. “Tristan has been consistently cheating on Khloé,” a source told PEOPLE at the time. “He’s a serial cheater. And there will be more women to come out of the woodwork.”

Kardashian initially forgave the basketball player, as she wanted him to be present for the birth and early days with their baby. She later reflected, “My biggest fear was to be selfish and emotional (all understandable under these circumstances) during this time,” she responded to a fan on Instagram. “I had to have a lot of talks within myself to keep calm. I want True to look back at her baby photo albums and see love and complete bliss! She deserved to have her family in the room while she took her first breath! I’m proud at how I found the strength to do everything for True even before I met her.”

The new parents relocated to Los Angeles, where they seemed to be going strong as they rebuilt their relationship over the summer. “She is committed to keeping her family together,” a source told PEOPLE. “And Tristan has shown that he is committed to Khloé, so Khloé will make it work.”

2018: He and Khloé spend time apart — and rumors circulate that they’ve split

By the fall, Thompson had moved back to Cleveland for his NBA season, and Khloé and True ultimately stayed behind in Los Angeles. Sources told PEOPLE that their relationship was “up in the air,” though they reunited to spend Halloween together as a family.

In the months that followed, the couple sparked multiple split rumors as Kardashian continued to post cryptic quotes on social media, and Thompson seemingly remained out of the picture. A source later revealed to PEOPLE,“They’ve been living separate lives.”

2019: He cheats on Khloé with Jordyn Woods

In February 2019, reports surfaced that Thompson had once again been unfaithful, making out with close Kardashian-Jenner family friend Jordyn Woods at a party. He quickly responded to the news, tweeting and promptly deleting a post saying, “FAKE NEWS,” seemingly denying the reports.

Woods later confirmed the news on a March 1 episode of Red Table Talk, saying Thompson kissed her as she left an afterparty at his home, but that nothing more happened. “I’m no homewrecker,” she said.

After the interview, Kardashian tweeted,“Why are you lying @jordynwoods ?? If you’re going to try and save yourself by going public, INSTEAD OF CALLING ME PRIVATELY TO APOLOGIZE FIRST, at least be HONEST about your story. BTW, You ARE the reason my family broke up!”

She followed up with another tweet placing blame on her ex, too. “Tristan is equally to blame but Tristan is the father of my child,” she wrote. “Regardless of what he does to me I won’t do that to my daughter. He has been addressing this situation PRIVATELY. If Tristan were to lie publicly about what conspired,then yes I would address him publicly as well.”

In the wake of the scandal, a source told PEOPLE, “Khloé is doing okay. She’s still upset about what happened and talks about it a lot. But it really seems she is able to see what everyone else has been seeing for so long — that she was always too good for Tristan.” They added, “She deserves so much better.”

A second source told PEOPLE that things “never really went back to normal” between the couple since the first cheating scandal.

The duo hasn’t been photographed together since Jan. 13, when they stepped out for dinner at Craig’s in West Hollywood following the Cavaliers’ game against the Los Angeles Lakers.

2019: He steps out with someone new in N.Y.C.

In the two weeks following the Woods interview, Thompson was photographed with model Karizma Ramirez in New York City. The two ate at hot spot Carbone, and he was pictured bringing two cups of coffee back to his hotel one morning.

Ramirez was previously linked to singer Chris Brown in 2013, according to Page Six, and is followed by Blac Chyna on Instagram.

The outlet reported that Brown, 29, and Ramirez hit it off at New York night club Finale where she worked as a server. The model also competed in Hooter’s swimsuit pageant in 2010.

Ramirez did not immediately respond to PEOPLE’s request for comment.