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Josh Groban’s Relationships with 5 Actresses & a Singer before He Fell for a TV Star - Inside His Private Life

Olawale Ogunjimi
Apr 02, 2022
10:20 A.M.
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Josh Groban's relationship with his TV star lover of roughly five years is worth the admiration it has earned. However, before the "You Raise Me Up" singer found his fairytale ending, he was involved with a few other celebrities.


Josh Groban is an excellent entertainer blessed with a string of talents, which over the years have been recognized. 

The singer, songwriter, actor, and producer holds credit for being a multi-platinum recording artist, with popular songs like "You Raise Me Up" and "To Where You Are."

[Left] Josh Groban at the 72nd Annual Tony Awards at Radio City Music Hall on June 10, 2018 in New York City; [Right] Josh Groban and his lover Schuyler Helford holding a hedgehog while smiling. | Source: Getty Images


Groban quickly realized his flair for music and did not waste time studying in college. Instead, the gifted singer dropped out after a few months to pursue his dream as a singer.

Fortunately, his decision yielded the desired result, and he amassed fame as soon as he released his first solo album. Groban has sold nearly forty million copies of his works worldwide, including his hit albums like "Closer" and "Awake."

Josh Groban at 'The Elvis Duran Z100 Morning Show' on October 11, 2019 in New York City | Source: Getty Images


The singer's reputable career is not the only eye-catching detail about his life. Groban, a handsome, tall 41-year-old man, is yet to settle down, leading fans to inquire about his personal life.

The "You Raise Me Up" crooner once revealed that he has not enjoyed dating "ordinary women." However, when recounting an experience, the actor claimed he had a date with a woman who resorted to playing his music and dancing to it.

Josh Groban performs onstage during his "The Bridges" tour opener at Infinite Energy Arena on October 18, 2018 | Source: Getty Images


This was a red flag! However, it did not mean that Groban retired from dating. Instead, he fancied falling in love with celebrities.

Despite a hectic schedule involving tours, on-stage deliveries, and on-screen appearances, he held on to serious romances with these known female faces.

Here are details about the actor's love affairs throughout the years and his current relationship with his most recent love.



Groban labeled his relationship with "Mad Men" actress, January Jones, which ended in 2006, as his longest. In 2013, years after they dated, the singer admitted that their affection for each other was genuine. In his words:

"We dated for about two and a half years, and we were madly in love. It was definitely my longest relationship."

Actress January Jones and musician Josh Groban at the Closing Ceremony and premiere of "Chromophobia" at the Palais during the 58th International Film Festival May 21, 2005 in Cannes, France. | Source: Getty Images


Following their separation, Jones welcomed a son, Xander, with an anonymous lover, while Groban, single and without a child, mentioned that he had not given up on love. According to him: 

"I'd love to get into another serious relationship. I am a real romantic at heart."


Jones is not the only famous face with which he was linked. It was speculated that the "You Raise Me Up" singer shared an intimate bond with Katy Perry.

Groban confirmed the gossip by explaining that they were "good friends," and their connection was instantaneous. He said they:

"hit it off because we're both goofballs."



Although Perry was not the only celebrity girlfriend Groban ever had, she was the only singer he dated. The pair remain modest when making comments about their relationship to this day.

While they never officially dated or admitted it, the singers appeared as a couple on red carpet events and were declared an item between 2009 and 2012.

Host Katy Perry at the 2017 MTV Video Music Awards at The Forum on August 27, 2017 in Inglewood, California. | Source: Getty Images


Fast forward to 2017, Perry confessed that they were once romantically involved, adding that he inspired a song from her famous "Teenage Dream" album. She said:

"People say, 'Who is The One That Got Away about?' That's Groban, absolutely him."

A few years later, Groban revealed the truth about their relationship. In his words per The Sun: "Well, we did. We were both very private - so we realized we were better as friends."


Both former flames already have new partners but have maintained their friendship over the years. The actor confirmed that they were on good terms, even though they chose to remain just friends.

Concerning Perry's revelation about inspiring a song, Groban expressed his shock, adding that it felt sweet. According to him:

"And we've been very, very good friends to this day. She's the best. But, I was not expecting that. That was a double-take, and I spit out my coffee when I saw that."



The "Titans" series star, April Bowlby was Groban's second actress girlfriend. They dated for four months in 2009. 

Despite being romantically involved, the pair were rarely captured by paparazzi in public. In 2018, rumors had it that Bowlby was single and focused on her career.

April Bowlby at The Paley Center For Media Presents "Drop Dead Diva: Season One Finale" on October 7, 2009 in Beverly Hills, California. | Source: Getty Images



The only proof that Groban and Blair were in a romantic affair was a photo from their movie date in July 2010. The pair were seen leaving The Grove, West Hollywood, California.

Sources claimed their romance must have begun and ended on that date, as they were never seen together again. However, Selma later dated fashion designer Jason Bleick that same year.

Actress Selma Blair at the Build Series to discuss "Mom and Dad" on January 22, 2018 in New York City. | Source: Getty Images



After a dinner date, speculation about Groban's affair with Trachtenberg began in 2010. Still, it was not until the following year, when the couple was seen on a restaurant date, that the news broke.

After that, rumors of a possible relationship fizzled out until 2014, when Trachtenberg made a heart-melting comment about the singer via a tweet. 

Groban reciprocated the familiarity with another comment. However, the gossip did not last long as he became involved with Kat Dennings in the fall of 2014.

Actress Michelle Trachtenberg at the 83rd annual Macy's Thanksgiving Day Parade on the streets of Manhattan on November 26, 2009 in New York City. | Source: Getty Images



Groban and actress Dennings made their relationship public when they made attendance at the Beverly Hills Carousel of Hope Ball.

There, Dennings heard him sing for the first time. Dennings, who is not new to the entertainment business, felt her lover was talented and gushed about him during her appearance on "The Ellen Show" later that year. According to Dennings:

"Obviously you know how talented and amazing [Groban] is. But what you may not know is that he's one of those people who can sit at a piano and play anything, anything off the top of his [head] … he's just, he's just a genius."


Josh Groban and actress Kat Dennings 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, California. | Source: Getty Images

Dennings met the actor through her friend and co-star, Beth Behrs. While commenting on their bond, Behrs established that:


''They're in this crazy business, they're both very calm and mellow and wonderful, and he treats her like a princess, and it's amazing."

Actress Kat Dennings and singer Josh Groban at the 25th anniversary MusiCares 2015 Person Of The Year Gala honoring Bob Dylan at the Los Angeles Convention Center on February 6, 2015 in Los Angeles, California. | Source: Getty Images


It was not a secret that they were in love with each other. Groban explained that their inseparable bond was due to their similarities. In his words:

"Humor is such a huge thing for me, so, you know, the fact that we could talk about Monty Python and all sorts of weird other things, I was like, 'Okay yeah, we're on the same page."

Josh Groban signs copies of his new album "Stages" at Barnes & Noble bookstore on May 8, 2015, in Los Angeles, California | Source: Getty Images


While this seemingly perfect relationship crumbled, a close source maintained that the exes still share an admirable friendship. The source told E! News:

"It was a mutual breakup. They are still friends and care about each other, but it's not the right time for them now as a couple."



Groban has had quite a rollercoaster ride with many female celebrities, which ended in a split and a budding friendship, but that did not deter him from continuing the trend.

The actor has been hooked to Schuyler Helford, and it is now his longest-running relationship, displacing the Groban-Jones romance.

Helford is the daughter of the renowned TV producer and writer Bruce Helford. She has also written, directed, and starred in several on-screen works like her famous father.


Although her resume is not as padded as Groban's, she is more diverse in the Hollywood business. Helford became the singer's girlfriend after his relationship with Dennings ended.

They were seen holding hands at the 2018s Tony awards. To date, all seems to be well with the lovers, making them the cynosure of all eyes.

Helford is steadily updating fans about their relationship, which involves sharing many heart-melting moments with her beloved partner. 

Schuyler Helford and Josh Groban pose backstage at the hit hip hop rap improv musical "Freestyle Love Supreme" on Broadway at The Booth Theatre on November 7, 2019 in New York City. | Source: Getty Images


In 2019, she flaunted their playfulness in a classic-themed photoshoot where Groban held an umbrella above her head. The caption read:

"Sepia tones is for lovers."

Last year, the actress showed fans how her beau treated her to her favorite buffet dishes. She uploaded a short clip presenting the different foods prepared and set on the table by Groban.


The chef was seen rocking his apron and an infectious smile as he welcomed her to a savory experience. An excited Helford wrote

"After a long shoot night yesterday, I came home to this. @joshgroban surprised me with my own "Schuyplantation."


Despite their genuine happiness, it is uncertain when they will tie the knot or whether they will have kids. Before his romance with Helford became public, the singer admitted that he did not think of having kids.

Neither Groban nor his lover has commented on taking their relationship to the next level. However, what is glaring is that they are inseparable, and this is Groban's longest relationship, which may be a good sign of a happy ever after!