• Director

    Ryan O’Leary

  • Country, Year, Length

    United States, 2019, 14 min

  • Category

    Short Narrative

  • Format

    Digital (screening) – RED (shooting)

  • Festival Year


Cast: Sam Vartholomeos, Gracie Gillam, Reed Birney, Catherine Curtin, Libe Barer, Chris Bellant, Alexis Nichole Smith
Crew: Producers: Ryan O’Leary, Anthony Pedone – Screenwriters: Ryan O’Leary

After a rough breakup, Charlie Monahan dives headfirst into the world of online dating. Guided by his charismatic best friend, Rufus, Charlie meets the charmingly complicated Maggie Mae. Quickly learning the differences between expectations and reality, Charlie’s forced to confront the challenges of maintaining a relationship in the digital age. In an era where everyone’s connected, Charlie’s never felt more apart.

Ryan O’Leary is an award winning independent filmmaker from Monroe Township, New Jersey. After a successful international festival run in 2014, his first feature film, The Backseat, acquired distribution with Osiris Entertainment. The Backseat is now available on Amazon Prime and many other major digital platforms. The film picked up awards at the Manhattan Film Festival and The International Indie Gathering, as well as several other festivals. He’s also directed music videos and several short films including a fan film adaptation of the Vertigo Comic series Y The Last Man, the horror-comedy Jesus Christ!, and the true life drama Bruce’s Garden, starring Primetime Emmy winner and two-time Tony Award nominee André De Shields. His 2009 short film A Bloody Mess, starring SAG Award winner Robert Clohessy, screened at festivals across the United States, and won multiple awards at the Kent Film Festival and the Five Towns College Film Festival. HIs latest film, The Lost Weekend, stars Tony Award Winner Reed Birney, Catherine Curtin (Orange is the New Black, Stranger Things), Gracie Gillam (Teen Beach, Z Nation), Libe Barer (Sneaky Pete), Sam Vartholomeos (Star Trek: Discovery), and Chris Bellant (The Backseat, Loserville).

Filmmaker’s Note

The Lost Weekend is a painstakingly honest account of desperate romance in the digital age. How do we deal with disappointment when expectations don’t even remotely match reality? How does technology affect our basic personal interactions and closest relationships? Using real life experiences as my source of inspiration, this film will be a specific, yet relatable, exploration of these thematic questions. The Lost Weekend is also an incredibly personal story for me. Soon after graduating film school, my longtime girlfriend and producing partner left me when it seemed I needed her the most. Finally ready to move out of my parents’ house and about to start pre-production on my first feature film, my whole world turned upside down. I thought I had my present and future all figured out. I thought I was ready to be a real adult. I was wrong. Within days of breaking up, I started drinking for the first time. And at 22, I started doing things that most people get out of their system by the end of high school. Along with drinking, the other way I tried to fill the void left by my ex was to search for new love — or something like it — by diving headfirst into the world of online dating. Over the next several months, I met so many different people from that community. Some were sweet. Some were weird. Some were jerks. Through all these dates, I learned a great deal about how easily people project their hope and fantasy onto each other, and what happens when the truth of realty doesn’t line up with that. This story is an earnest reflection of relationships in today’s world. It’s undeniable that technology makes communication easier, yet more complicated. But all advances in technology reveal a universal truth about us as people; we’re all just reaching out for some kind of connection.