A few lucky ladies have been the girlfriend of Chace Crawford.

For most, Chace Crawford first caught people’s attention when he starred on the OG Gossip Girl, back before The CW was purchased and scrapped for parts.

Though that sort of hit can easily create one-note has-been actors, it hasn’t slowed him down. Among other projects, he has one of the most memorable roles on The Boys. Which is saying a lot.

Chace Crawford’s relationship history isn’t quite as high profile as the actor himself, however. But it’s also not a secret.

Who has dated Chace Crawford?

Anyone tuning into the OG Gossip Girl series couldn’t help but notice the jarringly handsome Chace Crawford as Nate Archibald.

That hasn’t changed on The Boys. Except that his character, The Deep, is a less likable person. A considerably less likable person.

It’s a testament to Crawford’s versatility as an actor that he can pull off both famous roles.

On June 12, Chace Crawford opened up on the Call Her Daddy podcast, revealing that he’d hooked up with another Gossip Girl alum.

He didn’t share who it was — and he may not have been referring to a member of the main cast.

This is more open than he tends to be about romance. He keeps his relationships close to his chest … and has been able to avoid a lot of weird drama as a result. But even so, we know of some of his past romances.

Chace Crawford and Carrie Underwood

In May of 2007, Chace Crawford began dating Country singer Carrie Underwood. This was during the absolute pinnacle of Gossip Girl‘s cherished grip upon popular culture.

The two hit things off quickly and dated for nearly a year. He even traveled with her when she went on tour.

They broke up in April of 2008. In fact, according to Underwood, their breakup happened via text.

Presumably, Chace Crawford had other relationships between April of 2008 and March of 2013.

Obviously, there’s no shame in a 5-year dry spell. But famous actors who also happen to be ludicrously handsome are less likely to experience those than others.

However, in 2013, he began dating fellow actor (and model) Rachelle Goulding.

Chace Crawford dated Rachelle Goulding

In March of 2013, both Chace and Rachelle were living — and working — in New York.

When Chace later moved to Los Angeles, the two ended up breaking up. That makes sense.

By 2014, Chace looked back upon their relationship on The Kyle and Jackie O Show by saying that they “had fun.” We certainly hope so. Otherwise, why be together?

Then, in 2015, Chace Crawford met someone else on the show Blood & Oil.

Rebecca Rittenhouse is an actor (with an unfortunate surname that is not her fault, obviously).

Even though the two are both actors and thus somewhat public figures, they avoided the public eye with their romance.

Chace Crawford and Rebecca Rittenhouse

Unlike those last two somewhat-high-profile relationships, this lasted longer. Chace Crawford and Rebecca Rittenhouse remained boyfriend and girlfriend until 2018.

It appears that they had a very amicable breakup. They continued to share and co-parent their dog, even walking the pup together in March of 2020.

In 2021, the exes even vacationed together — with friends. They had not rekindled their romance, however, as TMZ reported that they were simply “great friends.” Good for them!

Chace Crawford’s Girlfriend: Who ‘The Boys’ Star’s Dating Right … was originally published on The Hollywood Gossip.