Love knows no boundaries, and age is just a number, and for actor Casey Affleck, that statement rings truer than ever.
For over a year now, Casey has been swept off his feet by Caylee Cowan, and their whirlwind romance has been anything but discreet.
Caylee Cowan and Casey Affleck didn’t let their significant age gap be a hindrance to their whirlwind romance (Credit: PA Images / INSTARimages)
From heartfelt posts on social media to captivating appearances at Hollywood events, the couple has unapologetically flaunted their love to the world.
Let’s delve into the romantic story of how Casey Affleck met his younger girlfriend, Caylee Cowan, and how their love story began to blossom.
Casey Affleck’s Journey in Hollywood
Casey Affleck is a renowned American actor who has left an indelible mark in the world of cinema, garnering an impressive array of accolades, including a British Academy Film Award and a Golden Globe Award.
As the younger sibling of actor Ben Affleck, Casey’s acting journey started at a young age, making his debut in the PBS television film Lemon Sky in 1988.
Casey Affleck is the younger brother of Ben Affleck and started his acting career at a young age, racking up an impressive filmography (Credit: Hubert Boesl / DPA / Cover Images)
He then collaborated with acclaimed director Gus Van Sant, appearing in three of his films – To Die For in 1995, Good Will Hunting in 1997, and Gerry in 2002 – which laid the foundation for his rising stardom.
Casey’s breakthrough came with his leading role in Lonesome Jim in 2006. His exceptional portrayal of a grieving man in Manchester by the Sea in 2016 earned him an Academy Award for Best Actor, further cementing his position as a formidable star in the industry.
Casey Affleck as Lee Chandler in the 2016 drama film Manchester by the Sea (Credit: Amazon Studios / Roadside Attractions)
Not just limited to acting, Casey Affleck made his directorial debut with the mockumentary I’m Still Here in 2010 and showcased his voice talents in the stop-motion animated film ParaNorman in 2012 as Mitch Downe.
Throughout his thirty-five-year-long career, Casey has displayed compelling performances in films like Gone Baby Gone, Tower Heist, Interstellar, Ain’t Them Bodies Saints, A Ghost Story, and The Old Man & the Gun. He recently appeared in the biographical thriller film Oppenheimer.
Meet Caylee Cowan: Up-And-Coming Star
Hailing from Los Angeles, California, Catherine Caylee Cowan came from a Jewish background and was raised by a single mother as the youngest of three siblings.
After completing high school, she ventured into acting, honing her skills through theater productions including classics like Three Sisters, The Glass Menagerie, and Danny in the Deep Blue Sea.
Like boyfriend Casey Affleck, Caylee Cowan pursued an acting career at a young age, joining classic theater productions after high school (Credit: Xavier Collin / Image Press Agency / Abaca Press / INSTARimages)
Caylee’s breakthrough in the film industry came with her debut role as Jan in the American romance period drama Sunrise in Heaven. The film, based on Jan Gilbert Hurst’s book “His Sunrise My Sunset,” premiered on Netflix in April 2020, marking the beginning of her cinematic journey.
In 2021, she continued to make waves by playing the supporting role of Kathy Barnes alongside Nicolas Cage in the action comedy horror Willy’s Wonderland.
Her talent was further showcased when she took on the lead role of Penelope, a doe-eyed femme fatale, in the independent romantic thriller Frank and Penelope.
Caylee Cowan as Penelope in the 2022 romantic crime film Frank and Penelope (Credit: Rosebud studios)
2023 brought more recognition for Caylee as she starred as Farrah Lee in the biographical musical drama Spinning Gold and portrayed Felicity in the science fiction thriller Divinity, produced by Steven Soderbergh.
Her involvement in the production world was not limited to acting, as she co-executive produced Robert Rodriguez’s action-thriller Hypnotic and the 2019 documentary about refugees called The Peace Between.
Aside from acting, Caylee Cowan also tried her hand at executive producing an action-thriller film and a documentary (Credit: Koi Sojer / INSTARimages)
She continues to venture into new projects, including the upcoming movie Holiday Twist, directed by Stephanie Garvin.
Alongside her busy career, she shares her adventures with her followers on Instagram, offering glimpses of her travels and recent summer vacation with Casey Affleck.
When Did Casey Affleck and Caylee Cowan Meet?
Casey Affleck and Caylee Cowan’s love story began in January 2021 when they first crossed paths. However, it wasn’t until November of the same year that they decided to go public with their romance.
The world took notice when pictures of the couple passionately kissing in the street appeared on Page Six, confirming their relationship.
Casey Affleck proudly made their love Instagram official in a heartwarming post, referring to Caylee as “MY Love” who “ALWAYS shows up when it counts.”
In the now-deleted post, which included a selfie of Caylee lying in bed, the couple shed light on their shared values as they attended a Red Cross blood drive to help amid a blood shortage.
Caylee Cowan and Casey Affleck met in January of 2021, and they made their relationship public in November of the same year (Credit: Rocco Spaziani / DPA / Cover Images)
They celebrated their first year of meeting in January 2022, expressing their affection and admiration for each other in touching social media tributes.
In his post at the time, Casey’s heartfelt words depicted Caylee’s profound impact on his life, writing, “My girl, you make me a better man every day. You could push me and you could drag me and you could carry me, but instead you just walk with me and talk with me and make me laugh. You are a deep and tender woman with more girlfriend geem than anyone I ever met.”
He added, “I don’t know what I did to deserve you, but I am determined to figure it out and keep doing it forever. While it beats, you have a place in my heart. I hope you stay that long. I love you.”
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Caylee reciprocated the love, praising Casey for his vulnerability, sensitivity, and genuine nature.
Alongside two photographs of the couple, she penned in the caption, “You make me feel safe in this world. The shelter of your embrace gets me through the toughest days. In Vietnam, it is said that a nickname for one’s life partner is ‘my home’ and that is what you’ve become for me. A home.”
As their relationship flourished, the couple celebrated their birthdays with touching dedications on Instagram, showcasing their love and gratitude for each other.
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For her 24th birthday in March 2022, Casey dedicated an Instagram post for Caylee alongside black and white photographs from their vacation in Tulum, Mexico, writing, “Happy birthday @cayleecowan ❤️.”
Meanwhile, on his 47th birthday in August, Caylee shared some of her favorite photos of Casey she has taken the past year.
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In the caption, she gushed, “Caleb Casey Affleck today is the day you were born! I am so grateful that you are alive! To know you is to love you and to love you and be loved by you in return is a blessing comparable to nothing else on Earth. Everything I love about you is exactly everything that makes you who you are!”
Engagement rumors fueled further excitement in May 2022 when Caylee was spotted wearing a noticeable ring during a dinner outing with Casey. While the couple has not officially confirmed the engagement, their affectionate bond and shared moments suggest a promising future.
Casey Affleck and Caylee Cowan’s Age and Height Difference
Casey Affleck, born on August 12, 1975, is currently 47, while Caylee Cowan, born on March 19, 1998, is 25.
When the couple began their relationship in late 2021, Casey was 46, and Caylee was only 23, resulting in a significant age gap of 23 years.
Casey Affleck and Caylee Cowan share an age gap of 23 years, with a slight height difference of four inches between them (Credit: Abaca Press / INSTARimages)
At the time, Casey was dating someone much younger, while Caylee was dating someone twice her age. Despite this difference, their age gap doesn’t seem to concern the couple, as they are genuinely and deeply in love.
Beyond their age, the difference in their height adds another exciting aspect to their relationship.
Standing tall at 5 feet and 9 inches (175.3 cm), Casey Affleck towers over his much younger girlfriend by 4 inches (10.2 cm), as Caylee Cowan measures 5 feet and 5 inches (165.1 cm).
What Caylee Cowan Says About Being in Love With Casey Affleck
During the premiere of Spinning Gold in Los Angeles earlier this year, Caylee Cowan couldn’t contain her excitement when talking about her love for her much older boyfriend, Casey Affleck.
In an interview with People, she passionately expressed, “It’s the best thing,” as she described their relationship. Caylee believes being in love has profoundly impacted her life, making her see the world in a new light.
Caylee Cowan expressed her excitement over being in love with Casey Affleck, calling it “the best thing” and describing her much older boyfriend as “everything” (Credit: ABACA / INSTARimages)
“Being in love is just — makes your whole world just colored and beautiful,” she shared, acknowledging how it made her “fall in love with the little things again.”
Caylee couldn’t resist praising her boyfriend, whom she has faithfully supported while he films his new movie, The Instigators, with Matt Damon in Boston. Describing Casey as “everything,” she cherished their moments together on and off the set.
Recalling a memorable scene in the forthcoming film where Casey was dressed as a fireman, Caylee playfully shared, “He was in a fireman’s outfit, and I was just like, ‘Uh oh.’ If this man was a fireman, if this man was homeless, if this man had any other career, I’d [still] be like, ‘Mm, that’s the one.'”
Casey Affleck’s Past Relationships and Controversies
Before finding love with Caylee Cowan, Casey Affleck had significant relationships. He dated 42-year-old actress Floriana Lima in 2016, and they were a couple for some time, although they never publicly announced their breakup.
Before this, Casey was married to 44-year-old actress Summer Phoenix, sister of Joaquin and the late River Phoenix.
They tied the knot in 2004, but their marriage faced challenges, and they separated in late 2015 before finalizing their divorce in 2017. The former couple share two sons, 19-year-old Indiana and 15-year-old Atticus.
Casey Affleck was previously married to Summer Phoenix, tying the knot in 2004 but eventually separating in 2015 and finalizing their divorce in 2017 (Credit: INFphoto)
Apart from his personal life, Casey Affleck has faced controversies. In 2010, two sexual harassment lawsuits were filed against him by women who worked with him on the mockumentary I’m Still Here. The accusations were serious, involving “unwanted sexual advances” and abusive behavior.
Casey refuted the allegations and resolved the legal disputes outside of the court for undisclosed amounts. However, during his Best Actor campaign for the 2016 film Manchester By the Sea, the lawsuits resurfaced, drawing attention and scrutiny.
In an interview with the Associated Press in 2018, Casey expressed regret for being involved in such disputes, stating, “First of all, that I was ever involved in a conflict that resulted in a lawsuit is something that I really regret. I wish I had found a way to resolve things in a different way. I hate that.”
Casey Affleck faced accusations of sexual harassment in 2010, but the legal disputes were resolved outside of the court (Credit: Aurore Marechal / ABACA / INSTARimages / Cover Images)
He added, “I had never had any complaints like that made about me before in my life and it was really embarrassing and I didn’t know how to handle it and I didn’t agree with everything, the way I was being described, and the things that were said about me, but I wanted to try to make it right, so we made it right in the way that was asked at the time.”
Casey continued, “And we all agreed to just try to put it behind us and move on with our lives, which I think we deserve to do, and I want to respect them as they’ve respected me and my privacy. And that’s that.”