
The Lost Weekend 2019
"It was good until it wasn't."
Ryan O'Leary's *The Lost Weekend (2019)* dives into the messy aftermath of a breakup, following Charlie Monahan as he plunges into the highs and lows of online dating with his flamboyant best friend, Rufus.
Director: Ryan O'Leary
Cast







Frequently Asked Questions
What is The Lost Weekend (2019) about?
*The Lost Weekend* follows Charlie Monahan, a recently heartbroken man who leans on his best friend Rufus to reconnect with the dating world—only to find reality doesn't match the hype. His budding romance with Maggie Mae quickly unravels, revealing the cracks in modern relationships and the illusion of instant chemistry.
Who directed The Lost Weekend?
The film was directed by Ryan O'Leary, who brings a sharp, comedic edge to this exploration of love in the digital era.
Who stars in The Lost Weekend?
The cast includes Sam Vartholomeos as Charlie, Gracie Gillam as Maggie Mae, Libe Barer, Chris Bellant, and Reed Birney, with Catherine Curtin rounding out the ensemble.
Is The Lost Weekend (2019) worth watching?
Despite its short runtime, *The Lost Weekend* packs a punch with its witty script and relatable themes. While IMDb hasn't rated it yet, its blend of comedy and drama makes it a compelling watch for fans of sharp, contemporary storytelling.
How long is The Lost Weekend?
The film runs for 14 minutes.
About The Lost Weekend (2019) — A Sharp Short Film About Love and Online Dating Gone Wrong
Ryan O'Leary's *The Lost Weekend (2019)* dives into the messy aftermath of a breakup, following Charlie Monahan as he plunges into the highs and lows of online dating with his flamboyant best friend, Rufus. Their search for love leads to a whirlwind romance with the enigmatic Maggie Mae, but as Charlie navigates the gap between digital fantasy and real-world chaos, he's forced to confront the hollow promises of modern romance. Shot through with sharp humor and poignant moments, this 14-minute dramedy captures the absurdity and loneliness of dating in the internet age.
With a blend of comedy and drama, *The Lost Weekend* explores themes of connection and disconnection, where every swipe feels like a promise until it isn't. The film's snappy dialogue and relatable characters make it a standout short, offering a bite-sized yet resonant look at love's pitfalls and possibilities.