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Winnie, a dating blogger who anonymously writes under the pen name Luckless, goes viral for a post about a disastrous date with Holden, a perpetually single sports agent who refuses to settle. When Winnie’s boss offers her very own column on the popular lifestyle site, Mush, Winnie has no choice but to keep dating Holden for content. But things get complicated when feelings develop and Winnie learns that Holden has a teenage son.Read moreLess
Winnie, a dating blogger who anonymously writes under the pen name Luckless, goes viral for a post about a disastrous date with Holden, a perpetually single sports agent who refuses to settle. When Winnie’s boss offers her very own column on the popular lifestyle site, Mush, Winnie has no choice but to keep dating Holden for content. But things get complicated when feelings develop and Winnie learns that Holden has a teenage son.
The story
Winnie, a dating blogger who anonymously writes under the pen name Luckless, goes viral for a post about a disastrous date with Holden, a perpetually single sports agent who refuses to settle. When Winnie’s boss offers her very own column on the popular lifestyle site, Mush, Winnie has no choice but to keep dating Holden for content. But things get complicated when feelings develop and Winnie learns that Holden has a teenage son.
Watch trailerCast & crew
Paniz ZadeWinnie Rhodes
Brett DonahueHolden Fulls
Maria RicossaEvette
Dale WhibleyDirk
Jennifer GibsonInga
Lexie GalanteHeather (Party Guest)
Lauren HoweTracey Allendale
Lisa NortonGPS VoiceExplore the crew
- Producer
- Mary Petryshyn
- Director
- John Bradshaw
- Editor
- Rob Chandler
- Writer
- Courtney Cilman
- Director of Photography
- David Perrault

Steffi DiDomenicantonio
Liam MacDonald