Ed Westwick’s Dating History: All the Women Chuck Bass Has Dated IRL

Ed Westwick’s Chuck Bass in the beloved television series Gossip Girl has to be one of the most enigmatic characters in pop culture history.

Interestingly, there’s not much separating the British actor’s on-screen teen drama character from his real-life persona, when it comes to courting good-looking women. Ed Westwick has consistently been a heartthrob IRL and his dating history reads like the who’s who of Hollywood’s most beautiful and talented women. 

That said, the Me You Madness actor is off the market now since he tied the knot with long-time girlfriend Amy Jackson in a dreamy white wedding on the picturesque Amalfi Coast in Italy in August 2024. 

 

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Yet, his previous relationships have also garnered significant attention. From his whirlwind romance with co-star Jessica Szohr to the famous lockdown date night with South African model Tamara Francesconi, the list of the ex-girlfriends of Ed Westwick includes some of the most accomplished names in the business. 

With the news and enchanting photos of his dreamy wedding taking over social media, we thought it would be fun to rewind the reel and revisit Ed Westwick’s dating history.

All of Ed Westwick’s alleged ex-girlfriends and relationships

Before we jump into the juicy details of Ed Westwick’s dating History, let’s take a look at the timeline of his relationships with all his ex-girlfriends.

Alison Mosshart: 2008
Drew Barrymore: 2008
Jessica Szohr: 2008 – 2010
Phoebe Tonkin: 2011
Jessica Serfaty: 2017 – 2018
Tamara Francesconi: 2019 – 2021
Amy Jackson: 2021-present

Alison Mosshart (2008)

Profession: Musician and singer
How did they meet: Not known

Ed Westwick’s first-ever public relationship was with iconic musician Alison Mosshart. 

Their romance was short-lived but created a lot of buzz in 2008. Westwick and The Kills’ lead singer were first spotted hanging out at Lollapalooza and they reportedly spent the entire weekend together.

The pair were often seen at parties and industry events together, sparking rumours of their romantic involvement. A source told Ok! magazine that they were “definitely more than just friends.” 

However, the spark between the two celebs dialled down soon and they went separate ways after a few months of dating.

Drew Barrymore (2008)

Profession: Actor and TV show host
How did they meet: Allegedly at a party

The next name to go down in the list of Ed Westwick’s alleged girlfriends is Santa Clarita Diet star Drew Barrymore. The two never made their affair official but their romantic escapade in 2008 certainly stirred up the media.

The duo was reportedly seen getting cosy at a Kings of Leon concert, sparking rumours of a budding relationship. However, Barrymore and Westwick always maintained a coy silence about their alleged fling, leaving fans and media guessing.

Jessica Szohr (2008 – 2010)

Profession: Actor
How did they meet: On the sets of Gossip Girl

Ed Westwick went on a dating spree in 2008 it seems. Following his two short romances, he started dating Jessica Szohr, his co-star from the hit American series Gossip Girl. The two apparently fell in love while filming the show and for nearly two years, they gave fans a peek into their relationship.

They were quite the couple in the Entertainment scene back in the day, often seen together at red-carPet events and parties. Although they had an on-and-off relationship throughout the show’s run, they ultimately decided to part ways in 2010.

Szohr later opened up about their time together on the Chicks in the Office podcast, mentioning, “A lot of us dated, and when Ed and I got together, we really wanted to keep it under wraps.”

Phoebe Tonkin (2011)

Profession: Actor
How did they meet: Not known

After his breakup with Jessica Szohr, the dashing Ed Westwick found a new flame in Australian actress Phoebe Tonkin. Their romance kicked off in 2011, but it was pretty low-key, with not many public outings or media buzz. They were together for about three months before deciding to go their separate ways on cordial terms.

Fans loved the blend of British and Australian talent in their brief relationship, making it a memorable love encounter in the dating history of Ed Westwick.

Jessica Serfaty (2017 – 2018)

Profession: Actor
How did they meet: Not known

The British actor, who got entangled in sexual assault allegations (he was not prosecuted due to insufficient evidence), went on a love hiatus for a few years.

However, in 2017 he reignited relationship rumours with actress Jessica Serfaty. They met at the glamorous Corridors of Fame Academy, where their mutual love for acting sparked an instant connection. This led to a romantic relationship that lasted until 2018.

The couple was often seen together at various industry events, looking stylish and in love. Although they enjoyed a year together, they officially split and announced their breakup in September 2018, leaving fans reminiscing about their time in the spotlight.

Tamara Francesconi (2019 – 2021)

Profession: Actor and model
How did they meet: Through social media

Tamara Francesconi was was Ed Westwick’s lockdown romance. The South African model and the Hollywood heartthrob reportedly started dating in October 2019, as first made public by The Sun.

During a rare Instagram Q&A while in lockdown, Francesconi shared how they first connected, and it was pretty typical and Gen-Zish for Westwick. “He direct messaged me out of the blue saying Hi and I nearly fell off my chair. We then chatted for a while and he asked me on a date, which I assumed would be a dinner but instead, he took me to a butterfly sanctuary in Mayfair. We thereafter spent the whole day exploring London together, and the rest is History,” she explained.

 

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In April 2020, Francesconi went all out organising a cosy night in with Westwick, turning her living room into a movie theatre.

“What an angel,” Westwick wrote on an Instagram Story, sharing clips of the movie playing alongside a spread of snacks. But after two years of romantic bliss during the lockdown, the couple mutually decided to part ways in September 2021.

Amy Jackson (2021-present)

Profession: Actor
How did they meet: At a racing event

The last name to go down in the dating history of Ed Westwick, hopefully, is his now wife Amy Jackson. The two were first rumoured to be in a relationship in early 2022, although their first meeting happened in 2021. They met each other at the Silverstone race track during an Aston Martin event, where a connection was established, leading Westwick to invite her for a date to a dog-friendly café.

 

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Their relationship became public on Instagram in June 2022 when the Madrasapattinam actor posted a heartfelt birthday tribute to Westwick, featuring tender moments from their time together. She referred to him as the love of her life, describing their bond as a combination of “home and an adventure of a lifetime.”

In January, while celebrating Jackson’s birthday in Gstaad, Switzerland, the British actor proposed to the Supergirl star, presenting the ring on the picturesque snowy suspension bridge known as Peak Walk.

Westwick and Jackson exchanged vows in Italy, accompanied by a series of pre-wedding celebrations along the Amalfi Coast. “The journey has just begun,” the Gossip Girl alum shared on Instagram, posting the first of many photos of the couple in front of their garden altar at the Giardini del Fuenti in Salerno, Italy.

Before the wedding, the sweethearts organised a welcome party for their family, featuring pizza and pasta, followed by a private boat excursion around Capri, Sorrento, Ravello, and Positano with their loved ones. “It was the perfect start to our Love Story Weekend as the sun set behind the Faraglioni Rocks,” Jackson wrote on Instagram.

 

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While social media is abuzz with stunning pictures from their wedding, Westwick and Jackson officially married on 9 August during a small civil ceremony at the Connaught Hotel in London, as published in People. Their Italian destination wedding held on 24 August 2024, welcomed 220 guests who Travelled from the United States, India, and Europe for the three-day celebration.

(Header and feature image courtesy: Instagram/Tamara Francesconi/Amy Jackson)

This story first appeared Augustman  Singapore.