Meet Ray Romano's Four Kids

Ray Romano learned from his father Al Romano's shortcomings how to be a better parent to his four kids. Speaking to the Los Angeles Times in 2023, the iconic comedian and actor disclosed that Al was often unable to speak about his emotions freely or to express his love for his kids because his own father abandoned their family when he was only two. Although his father's lack of emotional expression played a huge part in the person he became, Ray ultimately vowed to change himself for the better for his kids. 

However, the "Everybody Loves Raymond" star admitted that despite his best efforts, he still believed he could've done better, saying, "I wish I was not that guy who feels uncomfortable expressing their emotions to their children and being able to have those open talks." Ray's fatherhood journey started in 1990 when he welcomed Alexandra "Ally" Romano with his wife, Anna Romano. In the following years, the couple became parents to identical twins Matthew and Gregory Romano and their youngest, Joseph Romano. 

As his kids grew up, they all started following their passions. However, when People asked Ray for his thoughts on his children following in his footsteps someday he joked that he would have to self-medicate just to cope with the idea. The legendary comedian also candidly detailed some of his reservations about it, confessing, "It's a little stressful to be honest with you because I know the business and I know even people that have 'it' don't get it." Still, despite everything, Ray couldn't be prouder of his four kids. 

Ray Romano and his wife, Anna Romano, ran into trouble shortly after they welcomed their first child, Alexandra Romano. Speaking on "Today" in 2009, Ray recalled how his minivan got towed when he went to bring his wife and newborn home from the hospital, and they were left with no choice but to hop in a taxi. Thankfully, Alexandra's younger years went far more smoothly, and she even got to make cameos in "Everybody Loves Raymond" and "Ice Age: Continental Drift." Ultimately, though, Alexandra took a more traditional life path and graduated with a Bachelor of Arts from the University of Southern California. She worked her way up the ladder and nabbed a directorial position at a public relations agency, and later started working in the Advertising department of Prime Video. 

Her personal life is equally fulfilling since she found love with Zachary Wilezol. Alexandra revealed to People in 2024 that their paths first crossed at a Manhattan nightclub, and mutual friends had helped them to connect. "He spilled martinis all over me and told me I looked like Carmella Soprano — I was smitten," she sweetly recalled. Then, during a 2023 appearance on "Live with Kelly and Mark," Ray announced that Alexandra was engaged to Wilezol and she had broken the news to her parents by casually sharing a snap with the ring on. The comedian joked that he was hoping his next projects would perform well so that he could finance the doves at their wedding. The happy couple tied the knot in 2024.

Ray Romano reminisced, in a 1996 chat with People, about how Anna Romano called him after a sonogram during her second pregnancy to inform him that they were having twin girls. Although Ray couldn't be happier about the news, he secretly hoped their second child would be a boy. So, his joy only doubled when Anna told him she was joking and that they were actually having twin boys. The happy couple welcomed Matthew and Gregory Romano on January 12, 1993. While their sister made brief appearances on "Everybody Loves Raymond," the twins almost made their mark on the hit show in a very different way. 

The beloved sitcom dad was supposed to have twin boys named Matthew and Gregory in the pilot, but Ray decided to change their names to Michael and Jeffrey to maintain a clearer distinction between his on and off-screen lives. During a 2024 Variety interview, the twins acknowledged that they felt a bit directionless after dropping out of college without making an honest effort to excel. Although the boys ended up contributing to "Jimmy Kimmel Live!" and "The James Corden Show" as production assistants, they still felt like they ought to be doing more to create a career with real longevity. 

During this time, Matthew even auditioned for a part on "Survivor" but ultimately bowed out of the opportunity because he didn't believe he would survive the long-running reality show's infamously harsh conditions. Ultimately, Ray opened up about the twins' career issues to Mark Duplass, and the indie filmmaker gave them a life-changing proposition. 

During Gregory and Matthew Romano's Variety interview, they shared that Mark Duplass gifted them a camera and encouraged them to film anything that they found interesting. Eventually, the footage the boys recorded became "The Romano Twins" documentary, which chronicled their life experiences and growing pains from 2018. In their film, Matthew ventured into the wild to find meaning, while his brother followed in their father's footsteps and tried to become a stand-up comedian. Unfortunately, Gregory didn't do quite as well as he had hoped, and Ray Romano was understandably upset by his disappointment. 

As the "Ice Age" star pointed out to People, in December 2024, "You see him go to these horrible dives to try and do stand-up, and not be so successful, and it kills me." Ray continued, "I just want to grab you by the shirt and say, 'You're not supposed to do well for the first five years.'" However, he was still immensely proud of Gregory for shooting his shot in the first place and believed he would have only gotten better if he just kept at it. Meanwhile, his son argued that he didn't succeed with stand-up comedy because he "put too much pressure on [himself]." 

While the ambitious twin brothers are still figuring themselves out, Matthew's life saw a majorly positive change in 2024 when he tied the knot with his long-time partner, publicist Erica Markle. In a chat with Brides that very same year, Markle shared that her best friend had attended high school with Matthew and introduced them in 2015. And seven years later, he eagerly popped the question.

In February 1998, Ray and Anna Romano welcomed their youngest child, son Joseph Romano. During a 2017 appearance on "The Tonight Show With Jimmy Fallon," Ray used five words to hilariously describe his then-18-year-old son: "He thinks he's the s***." The "Everybody Loves Raymond" star clarified that Joseph got a kick out of being unpredictable and made his case by pointing out how he had become an ordained minister without even bothering to tell his father. After a friend of Ray's made him aware of it, he questioned his son and got a nonchalant "Pretty much" in response. Likewise, when the actor appeared on "Jimmy Kimmel Live!" in 2019, Ray elaborated that he was also unsure of how to talk about his youngest child because he could either be "the dumbest kid" or "the deepest." 

For instance, the Emmy winner once caught Joseph coming home from a party at 6 a.m. and tried telling him off for the late-hour entry. However, his son threw him into a complete spiral by simply answering that he was only arriving at 6 a.m. "for now." As Ray admitted, "I swear to god, [he] blew my mind. Because I started thinking, he's right. Time has no meaning." The "No Good Deed" star's confusing spiral extended even further when his wife inquired if Ray had learned of their son's whereabouts because he could only give a philosophical answer. Although Ray may have jokingly ranked Joseph as his least favorite kid during another appearance on "The Tonight Show With Jimmy Fallon," the quirky youngster's life still inspired his famous father to take a somewhat unusual career path. 

Despite initially not wanting to, Ray Romano made his directorial debut in 2022 with "Somewhere In Queens." The comedian also co-wrote, produced, and starred in the film alongside Laurie Metcalf and Jacob Ward. Although the heartwarming flick revolves around its main character, high school basketball player Matthew "Sticks" Russo, it was actually Joseph Romano who inspired the movie. In a 2023 chat with The Wrap, Ray confirmed that the idea for the film started brewing after he watched Joseph, who was the best player on his school's basketball team, taking part in his final game. Afterwards, the parents and the team all hugged the coach, and Ray got emotional because it was the end of an era. 

Additionally, the Emmy winner wasn't too proud to divulge that he would miss getting a pat on the back for raising the MVP of the basketball team. Likewise, when the "Everybody Loves Raymond" star was interviewed by People in 2023, he confessed, "I used to love going to the games, and I would live vicariously through him with all the excitement." Ray continued with a joke, "I mean, it's kind of sad that I needed more excitement in my life. I was a TV celebrity." Unfortunately for the comedian, Joseph's basketball career ended in high school. However, Ray still got to happily sit on the sidelines and watch his youngest son make a cameo in both his directorial debut and "Ice Age: Dawn of Dinosaurs."