It was a long journey for him to arrive at this exciting moment, but the turning point was when he was streaming Star Trek: Discovery from his home in Austin and witnessed a same-sex kiss scene between two out actors, Wilson Cruz and Anthony Rapp.
Pintauro was a child actor who played Jonathan, the son of divorced advertising executive Angela Bower played by Judith Light in the popular 80s sitcom Who's the Boss?
After the show ended on April 25, 1992 after eight seasons, Pintauro took a hiatus from professional acting and attended Middlesex County College in Edison, New Jersey and later Stanford University to study English and theater.
Before graduating in 1998, he was faced with a series of blows.
He was outed as gay by the tabloid paper The National Enquirer in 1997 at a time when there were hardly any gay actors.
"I'm trying to study, and suddenly I'm having to deal with this," he recalled of the time he gave the tabloid paper an interview to control the narrative after they threatened to reveal his sexuality–even though he had already been out to friends and family.
Although he was initially "angry," he felt solace in the amount of support from fans telling Pintauro they were inspired by him after the publication of the article.
Pintauro disclosed he struggled financially when he moved to New York City to try his hand at directing. After he depleted his child-star savings at Stanford, he took on several jobs–including working in plays or waiting tables.
During that time, he fell in with the wrong crowd and became addicted to methamphetamine.
In 2015, he announced he had been diagnosed with HIV after an unsafe sexual encounter while high on crystal meth in 2003.
As he began taking medication for the virus, Pintauro reclaimed his life on his own terms without going to rehab and he weaned himself off of drugs.
He eventually returned to LA for a fresh start.
However, his ambition of working again as an actor was not in the cards for him right away.
"Auditions were very few and far between," he recalled, and a failed attempt on getting a cameo on Will & Grace didn't help his self-esteem.
As a result of "months of runaround" after he bought his way on the show through a charity auction, he decided not to go through with filming the NBC sitcom after all.
"It brought back all of that trauma of not feeling wanted," he said of that particular experience.
Pintauro moved on from show biz and tried to make ends meet by working as a manager at P.F. Chang's, a casting assistant and a Tupperware sales consultant.
All that is behind him now and his future is looking much brighter.
Pintauro found love and married his husband Wil Tabares in April 2013.
Three years later, they relocated to Texas, where Pintauro worked for Austin Pets Alive as a veterinarian technician.
While he thought working professionally as an actor was a closed chapter, he began realizing that his itch to get back into acting never really waned.
His epiphany was spurred on after seeing the "beautiful kiss" between Cruz and Rapp on Star Trek: Discovery that influenced his desire to get back in the game.
Up until this moment, he admitted to having "a lot of trauma from my time after Who's the Boss?"
During the show's later seasons when his character reached his teens, Pintauro recalled that producers of the sitcom "didn't really know what to do with me."
He wasn't out then, but Pintauro said his sexuality was "obvious to others" and that producers "didn't feel like my character dating a girl was believable."
"They don't want me to be here," said Pintauro, with the exception of his castmates whom he said were all "great."
But the 46-year-old was impressed at how much things have changed, with more prominent LGBTQ+ actors getting roles in TV and film.
He said "something just clicked," adding, "I finally felt ready."
Pintauro told Tabares about wanting to be an actor again and subsequently quit his job, contacted his former manager and secured an audition.
He landed a role on A Country Christmas Harmony where he played Eugene, a happily-married gay best friend and assistant to a country singer–played by Brooke Elliott–who is trying to revitalize her career.
Looking back on the whirlwind of events and nailing his first audition, he said:
"I couldn't believe it."
He told Hollywood Life:
“Because I’m coming back to the business for the first time in a very long time, my manager and I made the decision that I will audition for pretty much anything that comes up that’s interested in having me because I just need to build a new resumé."
“The audition came first and I was like, yes, whatever it is, I’ll do it. And then I got the material and started reading it."
"My favorite part about it is you know how in Christmas movies there’s always some character that tells the lead character, ‘You’ve got this.’ Like, three-quarters of the way through the movie ‘go get them’ kind of moment. My character had that."
"I started reading it and he’s just so smart and caring about Chrissy, Brooke Elliot’s character, that I was instantly way more excited about it."
"I had about three hours to put together the audition. As soon as I discovered that this was exactly the kind of role that I was looking for I really just jumped in and made it as good as I could in three hours.”
Pintauro praised Lifetime's LGBTQ+ representation and inclusion efforts in their recent programming.
“The Christmas movie genre was by far the biggest holdout when it came to starting to do representation, especially for the LGBTQ+ community," he said.
"I’m so proud of the strides they are making."
“That was the other thing. This is a real gay character. My character’s married."
"The whole second sort of subplot of the movie is about my marriage and how hard it is for me to be away from my husband."
"I was just sort of flabbergasted that that was the case. I’m so proud of them.”
Who's the Boss? also starred Tony Danza, who played Tony Micelli, a former major league baseball player who becomes a live-in housekeeper and raises his daughter Samantha played by Alyssa Milano.
Milano couldn't be more elated of her younger brother co-star's return to Hollywood.
"I'm very proud of Dan," she said.
"Not only for following his lifelong dream but even more so for being a good person and staying true to who he is despite the hardships he's faced."
There is a possibility the two may reunite on Amazon Freevee's upcoming Who's the Boss?sequel series in which Danza and Milano will be reprising their roles as father and daughter–30 years after the events of the original series.
But as to his involvement in the project, Pintauro was cryptic as he and Judith Light reportedly had only expressed their support for the sequel series.
"I've been involved in some conversations," he teased.
Fans of the show will have to wait and see until further official announcements are made.
A Country Christmas Harmony premiered on Lifetime on November 18.