Since his early “Gossip Girl” days, Chace Crawford’s love life has been a source of interest for fans. The 36-year-old actor, who plays The Deep on “The Boys,” has been linked to a handful of celebrities.

Including Erin Andrews (of “Dancing With the Stars”) and Ashley Greene (of “Twilight”), but only three have been officially confirmed relationships. Hookup allegations have also circulated, including with “Gossip Girl” star Taylor Momsen and fashionista Lauren Conrad.

Crawford’s personal love life appears to be considerably more calm back than his tumultuous and dramatic romances with Blake Lively’s Serena and Leighton Meester’s Blair on “Gossip Girl.”

The Texan actor, who made his cinematic debut in the supernatural movie The Covenant (2006), joined the cast of “Gossip Girl” in March 2007 and rapidly became one of television’s most eligible bachelors in the role of Nate Archibald.

Crawford told Us Weekly in 2019 that he “had been dating around a little bit, but, you know, nothing serious.” This prompted speculation about whether or not he was now single. His online profiles suggest he could still be available. Continue reading for a brief overview of Crawford’s romantic relationships throughout the years.

How This Stud Has Been Romantically Involved In The Past

Stay with us until the end to find out which women have won his heart in return; we’ve done some digging into the “Gossip Girl” star’s past relationships and prepared for you what we think is a comprehensive list of the stunning ladies he’s been associated to romantically.

Chase Crawford And Shauna Sand

Chace Crawford’s first high-profile liaison was with ex-Playmate Shauna Sand, but he was rumoured to have had relationships with other women before his fame. During an interview for Star magazine published in November of 2009, she revealed that the two of them first met in August of 2003, when he was just 18 years old.

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Initially sighted in October at Manhattan’s Marquee nightclub, the couple was later spotted at the Rose Bar in the Gramercy Park Hotel. She told People magazine, “I’ve met him and he appears to be a very lovely guy.” Chase is extremely cute.” He’s got neat hair, a good build, and stunning blue eyes.

Their relationship didn’t last long, ending in early 2008, and a month later, Carrie revealed the news of their breakup to Extra magazine, adding, “It was absolutely mutual.

There’s no hard feelings; we just texted each other our breakup. It just didn’t work,” she continued. We were both aware that it was a futile effort, yet we held no animosity toward one another as a result.

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Chase Crawford And Rebecca Rittenhouse

Despite being together for three years, Crawford and Rebecca Rittenhouse decided to end their relationship in 2019. When the two actors first met in 2016 while filming Blood & Oil, they seemed like they could be meant for each other forever.

However, the Gossip Girl alum made the announcement that he was “casually dating” again very soon after these two broke up.

In May of last year, Crawford admitted he was “dating around,” and before any woman could begin plotting how to capture the TV heartthrob’s affection, Crawford said, “That’s it! Knicks tickets and a pizza.”

Rachelle Goulding And Chace Crawford

From 2013 until 2014, they were an item. The Covenant actor opened up about his current relationship status with Goulding, saying, “It’s entirely good… totally good,” and adding that he and Goulding “had fun” together before breaking up.

To the two young ladies, Chace Crawford and Ashley Greene

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In 2009, the Boys actor and the Twilight star were caught in more than one extremely public embrace. A source told E! News at the time that the two had hooked up in the past while “he lived in L.A.,” but that their sexual encounters were “never anything serious.”

Chace Crawford And Carrie Underwood

The country artist claims that the pair’s attempts at a romance “simply didn’t work.” Underwood said to Extra at the time of the cute couple’s 2008 breakup, “We both felt the same way.” We ended things amicably by text message, and neither of us has any ill will toward the other.

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Chace seemed to agree with Carrie’s assessment of the situation and then quickly resumed playing the field for a hot minute, so it’s unclear who texted their breakup first.

The actor from The Boys may have been onto something when he said that the “keys” to his heart were easy to figure out. If his past relationships teach us anything, it’s that pizza is the key to Chace Crawford’s heart.


Chace Crawford, at 35 years old, is widely regarded as one of Hollywood’s most eligible bachelors since since his breakup with a stunning actress. We hope he finds the one who shares his love of Knicks games, pizza, and settling down and sends her our best wishes.

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