From different flings to whirlwind engagements, "Saturday Night Live" star Pete Davidson had his fair share of ups and downs in the love department.

On Tuesday, the 25-year-old comedian was spotted spending time with 18-year-old supermodel and daughter of Cindy Crawford, Kaia Gerber. They were seen at Sadelle's in New York City.

Davidson and Kaia were in a booth, sipping drinks and chatting -- sparking rumours that the two could be dating.

E! Online also reported that Pete was seen leaving the supermodel's apartment on Wednesday, but they claimed that the two are just friends.

Pete seems to be doing just fine after his split from his high-profile girlfriends. Him jumping to relationship after relationship seems a bit fast, though.

After being dumped by Ariana Grande, OK! Magazine reported that Pete Davidson has been extremely depressed. Just before this new fling, he was all lovey-dovey with A-list star Kate Beckinsale and Margaret Qualley.

Let's go back to the start and re-count Pete Davidson's dating history.

2015: Carly Aquilino

Pete briefly dated 27-year-old Carly Aquilino. The star appeared in "Girl Code" and has a lot to say to his ex's engagement to Ariana Grande back in June 2018.

When the news broke that Pete and Grande were engaged, she took to her Instagram Stories to share a photo of a text message from a friend who wrote, "I know I'm the 9 billionth person to text you about this but... I can't." Carly responded with "HAHAHAHAHAHA" and captioned the story, "MY DAY IN A TEXT MESSAGE."

According to E! News, Carly Aquillino and Pete Davidson are still in good terms. They were once spotted together in New York.

2016: Cazzie David

Davidson then dated 25-year-old Cazzie David in 2016. She is the daughter of "Seinfeld" creator, Larry David.

In a 2016 event at the Natural Resources Defense Council Stand Up for the Planet benefit gala, he gushed about his then-sweetheart. He told ET, "She's the most beautiful girl in the world, look how lucky I am. She's so smart, look how smart she is. She is a very, very wonderful lady."

Cazzie also played a part in Pete's sobriety, saying, "I'm fortunate. She's a very, very supportive person."

Unfortunately, the couple split in 2018, but the comedian still had a lot of good things to say about his ex: "She's a very talented girl. She'll do great; she'll be fine."

2018: Ariana Grande

In 2018, Pete started dating pop star Ariana Grande, shortly after they have broken up from their respective relationships. Pete from Cazzie, while Grande, from the late rapper, Mac Miller.

Their romance was the most controversial topic in 2018. The two got engaged just one month after they started dating.

However, the two broke up in October. From a source that told ET, "Ariana made the final decision. It was time to realize this wasn't the right time for them, and Pete is incredibly heartbroken."

2019: Kate Beckinsale

Pete moved on from Ariana pretty quickly. At the Golden Globes after-party, Pete was seen being super flirty with 46-year-old actress Kate Beckinsale.

In March, Kate told The NY Times, "I've never been in this position before - never dated anybody who comes with their bag of mischief. It's all quite shocking and something to get used to."

After four months, their romance fizzled out. They were no longer dating but remained friends.

2019: Margaret Qualley

US Weekly broke the news that Pete Davidson was dating "Once Upon a Time in Hollywood" actress Margaret Qualley in August 2019. "They've been seeing each other for a couple of months and Margaret is excited about him," the source told the magazine.

However, two months later, their romance was over. Similar to Kate, the two remained friends.