Teenage Badass actress, Elsie Hewitt, is currently glowing due to her pregnancy. The mom-to-be proudly flaunted her baby bump in a swimsuit and posted some happy vacation photos on Instagram on August 29, 2025. In the post, her boyfriend, Pete Davidson, was seen planting a sweet kiss on her forehead as she took a mirror selfie in a luxurious bathroom. The internet has been flooded with glimpses of Elsie’s latest update, with growing interest in her dating history.

Elsie Hewitt’s publicly known relationships include those with four celebrities: Ryan Phillippe, Benny Blanco, Jason Sudeikis, and Pete Davidson. The relationships included peaceful splits with no harsh feelings for some, and ugly breakups with others. Thus, she can be said to have had a wide range of dating experiences. Here’s a look back at her relationship timeline.

Elsie Hewitt’s brief romance and messy breakup with Ryan Phillippe

Model and actress, Elsie Hewitt had a brief, contentious relationship with Ryan Phillippe in April 2017. Ryan and Elsie were first romantically linked in April 2017, and they dated for about three months. In July 2017, the couple had an altercation at Ryan’s Los Angeles home, and in September 2017, Elsie alleged that he had physically abused her. She filed a USD 1 million civil lawsuit against him when she was 21 and he was 43. Ryan filed a countersuit, accusing her of defamation and extortion.

Both the domestic a**ault lawsuit and its countersuit ended in a settlement between the two parties outside the court, in October 2019. It took place just days before the case was about to go to trial, and the reason for the settlement remained undisclosed.

Elsie Hewitt’s one-year relationship with Benny Blanco ended in a quiet split

American songwriter and Selena Gomez’s fiancé, Benny Blanco, dated Elsie from 2019 to 2020. The ex-couple met on the set of the music video for Blanco’s 2019 song Graduation, featuring Juice WRLD, in which Elsie appeared. In October of the same year, Elsie made her relationship with Benny public by posting a tweet for National Boyfriend’s Day. After three months, Benny also confirmed their relationship through an Instagram update and then appeared together on the red carpet at the 2020 Spotify Best New Artist Party.

Elsie and Benny ended their relationship sometime in 2020, though the exact details have not been publicly disclosed. Benny is known to be a private person, and thus, the reasons for their breakup remained under wraps. Last year, Elsie reminisced on their relationship during her March 2024 appearance on In Good Company podcast, and said:

“I get a little bit salty when my friends go to his house. I’ll always love him.”

Elsie Hewitt’s dating rumours with Jason Sudeikis

Ted Lasso actor, Jason Sudeikis and Elsie Hewitt might have had a brief, low-key romance in 2024. In January of the year, Jason and Elsie sparked dating rumours when they were seen on a night out in West Hollywood. Paparazzi photos captured them acting affectionately toward one another outside of the Bird Streets Club. After six months, an anonymous source told Life & Style that the pair were happy together, with Sudeikis enjoying his new, casual relationship. The couple was seen together again in public when they attended the U.S. Open in New York City. Later that year, they reportedly parted ways quietly.

Elsie Hewitt might have found ‘the one’ in Pete Davidson

After the buzz around Elsie and Jason Sudeikis subsided, she began dating The Pickup actor, Pete Davidson, in March 2025. The couple are now expecting their first child. On July 16, 2025, she announced her pregnancy on Instagram, sharing photos of a sonogram and her baby bump. The couple has since moved in together in New York. Currently, the 29-year-old is enjoying a tropical getaway with her 31-year-old baby daddy.

What are your thoughts on Elsie Hewitt’s relationships with her exes before becoming Pete Davidson’s baby mama? Let us know.