Calling It Quits
“Sometimes your eyes don't see what your heart already knows.”
We checked 8 streaming services in India on 04 Jun 2026 at 22:10 IST
About
Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him.
Cast
Dennis Boutsikaris
as Dante
Jessica Hecht
as Cynthia
Robert Clohessy
as Jake
Marc Bonan
as Young Dante
Robert Aberdeen
as Gastroenterologist
Julie Berndt
as Deborah
Matty Blake
as Cal
Kristen Bush
as Young Alba
Orlagh Cassidy
as Marcy - Agency Exec.
Casey Cipriani
as Meditation Student
Michael Cullen
as James - Agency Exec.
Patrick Edgar
as The Customer
Aryn Elaine Cole
as Waitress
Paul Fears
as Roommate
Glory Gallo
as Alba
Anitha Gandhi
as Sharon
Mika Gill
as Highschool Girl
Michelle Glick
as Karen
Katie Groves
as Bartender
Tasha Guevara
as Cashier 2
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About Calling It Quits
“Sometimes your eyes don't see what your heart already knows.”
Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him. Running 86 minutes.
Calling It Quits Cast and Characters
The cast features Dennis Boutsikaris (as Dante), Jessica Hecht (as Cynthia), Robert Clohessy (as Jake), Marc Bonan (as Young Dante), and Robert Aberdeen (as Gastroenterologist). Their performances are a major reason Calling It Quits has built such a passionate audience.
Where to Watch Calling It Quits Online
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▶ Watch Calling It Quits NowWhy People Are Watching Calling It Quits
Calling It Quits flies under the radar but it deserves your attention. What makes it work is emotional weight that hits where it counts. If you enjoy English storytelling that doesn't follow the same tired beats, this is the kind of film you'll end up recommending to friends.
Frequently Asked Questions about Calling It Quits
Where can I watch Calling It Quits online for free?
You can watch Calling It Quits online free on Bowood.TV. Just open the page and hit play — no signup, no subscription, full HD streaming on phone, tablet, or desktop.
How long is Calling It Quits?
Calling It Quits runs for 86 minutes (about 1.4 hour).
Is Calling It Quits good? What's the rating?
Calling It Quits holds a 0.0/10 rating based on 0 reviews — a niche pick worth checking out.
Who is in the cast of Calling It Quits?
The main cast includes Dennis Boutsikaris, Jessica Hecht, Robert Clohessy, and Marc Bonan, plus a strong supporting ensemble.
Is Calling It Quits available in English?
Yes — Calling It Quits was originally produced in English and that's the version you'll stream here on Bowood.TV.
When was Calling It Quits released?
Calling It Quits was released in 2009.
Do I need an account to watch Calling It Quits on Bowood.TV?
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Frequently Asked Questions
Common questions about Calling It Quits
Where can I watch Calling It Quits for free?
You can watch Calling It Quits (2009) online for free on Bowood.TV. Just click "Watch Free" on this page to start streaming instantly — no account, subscription, or downloads required.
What is Calling It Quits about?
Calling It Quits is a Drama English-language film. Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him.
When was Calling It Quits released?
Calling It Quits was released on January 1, 2009. It has a runtime of 1h 26m.
Who stars in Calling It Quits?
Calling It Quits stars Dennis Boutsikaris, Jessica Hecht, Robert Clohessy and Marc Bonan. The full cast list is available in the Cast section above.
Is Calling It Quits available in HD?
Yes, Calling It Quits is available to stream in high definition (HD) on Bowood.TV. Our players automatically deliver the best quality your connection supports — no extra setup needed.