Josh Groban once shared that he hasn't had the best of luck dating "ordinary" women; however, he has a reputation for stealing the hearts of various famous women. One of the singer's former flames even said he was "the one that got away."
During a February 2013 interview with Details Magazine, Josh Groban opened up about his love life. The singer-turned-actor spoke about his past loves and shared that he was single at the time but remained hopeful of finding new love.
He had already gained a reputation for having previously dated well-known women in entertainment, though he tried cultivating relationships with women who weren't accustomed to the spotlight. However, his attempts usually didn't work out so well.
Josh Groban attends The 76th Annual Tony Awards at United Palace Theater on June 11, 2023, in New York City. | Source: Getty Images
Groban recalled one date when he invited his suitress over, and she looked for music to play while they had a glass of wine. "She played rough mixes of my new record and started dancing to it. I was like, 'Don't do that. Groupie alert, groupie alert,'" he said.
The Hollywood star added that he can't get "turned on" by his own music. This was only one experience he shared with a non-famous woman, but his romances with other TV stars so far have been blissful.
Josh Groban attends a conversation with Alex Edelman at 92nd Street Y on June 25, 2023, in New York City. | Source: Getty Images
January Jones
Groban's first known former flame is actress January Jones. The pair dated between 2003 and 2006 and frequently made public appearances as a couple. They separated mid-2006, with Jones' rep confirming they were "taking a break" but were still friends.
In an interview years later, Groban reportedly said he and Jones were "madly in love." At the time, his relationship with the "Mad Men" star had been his longest. Still, he hoped to find another long-term romantic commitment because, as he said, "I am a real romantic at heart."
When he opened up about their separation in February 2013, Jones had become a mother; her son, Xander Dane Jones, was 16 months old, but the little one's father's identity was yet to be revealed.
January Jones and Josh Groban during the 2005 Vanity Fair Oscar Party at Mortons on February 27, 2005, in Los Angeles, California. | Source: Getty Images
Katy Perry
Groban briefly touched on his connection to Katy Perry during his Details interview. When asked about the nature of their relationship, he shared that they had met before Perry released her debut album.
"We're very good friends. We met before her first album was even released, and we hit it off because we're both goofballs," he explained. When further pressed about the subject, bluntly asked if they dated, he divulged, "No, not really... We might have skated on the line of dating."
By the time Groban addressed the speculation of their short romance, Perry was dating another singer, John Mayer. Many years later, during his appearance on "Watch What Happens Live with Andy Cohen," a fan called in and revived the subject.
Katy Perry arrives at NBC's "Carol Burnett: 90 Years Of Laughter + Love" Birthday Special at Avalon Hollywood & Bardot on March 2, 2023, in Los Angeles, California. | Source: Getty Images
It was in September 2018, and the caller asked Groban about his thoughts on Perry, saying he was "the one that got away" in her 2010 song "The One That Got Away" during a livestream the previous year.
Groban was initially caught off guard by the question but said he thought it was "sweet" and was "flattered" that she said that. However, he became doubtful the song was about him when he heard the lyrics, as they mentioned a lover who had a tattoo and owned a Mustang.
Andy Cohen then joked, "I think you should call her back." Groban maintained that he and Perry were good friends and had tried dating privately but thought it best to keep things platonic. The "Dark Horse" singer previously wed Russell Brand and is now engaged to Orlando Bloom.
Katy Perry at the grand-reopening of the Landmark, Tiffany & Co.'s flagship store on April 27, 2023, in New York City. | Source: Getty Images
Selma Blair
Groban was romantically linked to actress Selma Blair in July 2010. The pair were spotted leaving a movie theater at The Grove in Los Angeles that month. It is unclear whether it was a romantic or friendly date, but they were not seen together afterward.
The following month, Groban reportedly enjoyed a dinner date with Michelle Trachtenberg. Blair had previously dated her former "Kath and Kim" co-star Mikey Day in late 2008. However, their romance was short-lived, as it reportedly ended in 2009.
Selma Blair poses backstage during the 2022 People's Choice Awards held at the Barker Hangar on December 6, 2022, in Santa Monica, California. | Source: Getty Images
Kat Dennings
Groban made his relationship with Kat Dennings official when they attended the Carousel of Hope Ball in Beverly Hills in October 2014. "They were so cute together! They were adorable on the carpet. She was whispering in his ear a lot, and they seemed really happy," one source said.
Groban was performing at the event, and it was the first time Dennings had heard him sing. Although they kept their relationship relatively private, they often raved about each other during interviews.
Kat Dennings and Josh Groban arrive at the 2016 Pre-GRAMMY Gala And Salute to Industry Icons Honoring Irving Azoff at The Beverly Hilton Hotel on February 14, 2016, in Beverly Hills City. | Source: Getty Images
They especially bonded over their love for humor, as Groban shared, "Humor is such a huge thing for me, so the fact that we could talk about Monty Python and all sorts of weird other things, I was like, 'OK, yeah, we're on the same page.'"
Sadly, their love story ended in 2016. News broke that August that they had separated amicably. A source revealed the former lovers still cared about one another and remained friends, but "it's not the right time for them now as a couple."
Kat Dennings and Josh Groban seen walking in Tribeca with there Dog on June 4, 2015, in New York City. | Source: Getty Images
Schuyler Helford
It's unclear when Groban began dating Schuyler Helford, but the former couple debuted their relationship at the 2018 Tony Awards. Much like his previous loves, Groban kept his romance with Schuyler private.
In 2019, Helford joined Groban when his parents celebrated their 50th wedding anniversary at a vineyard in Beaune, France. The actress shared a lovely photo of herself, Groban, his parents, and another gentleman and penned:
"Happy 50th anniversary to the incomparable Jack and Lindy Groban, who are living proof of lasting love!"
In March 2021, Helford wrote of a touching gesture by her beau. She shared that one of her favorite restaurants, Souplantation, had closed down due to the pandemic. After a long day of filming, she came home that evening to find that Groban had prepared her a Souplantation-style dinner.
"After a deep dive on the internet, he found the original recipes for my favorite dishes and made them from scratch," she gushed, adding that all the dishes tasted exactly like the original. The post was among the last few featuring Groban. It's unclear when they eventually separated.
Josh Groban and Schuyler Helford attend the Broadway Opening Night Performance of "Hadestown" at the Walter Kerr Theatre on April 17, 2019, in New York City. | Source: Getty Images
Natalie McQueen
Groban and actress Natalie McQueen are said to have started dating during the summer of 2022. Groban made their relationship Instagram official on Valentine's Day in 2023 with a short and sweet Instagram post.
"Happy Valentine's Day to this remarkable woman who makes me so gosh dang stupid happy," he wrote alongside a photo of him and McQueen in bed. They made their official red carpet debut at the opening night of a Broadway show the following month before attending the Met Gala in May.
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