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.
John Bradshaw
Director
Courtney Cilman
Writer

Paniz Zade
Winnie Rhodes

Brett Donahue
Holden Fulls

Steffi DiDomenicantonio
Kyra

Maria Ricossa
Evette

Dale Whibley
Dirk

Jennifer Gibson
Inga

Lexie Galante
Heather (Party Guest)

Liam MacDonald
Ty
Glen Michael Grant
Ret Fawkes
The Wrong Paris67%
Yoh! Bestie63%
Little Miss Marker66%
The Mistle-Tones61%
Psych: The Movie72%
Marrying Mr. Darcy61%
Easy Virtue64%
Relationship Goals62%
The Kissing Booth 276%
Saving Silverman58%
Only the Lonely61%
Little Italy66%
The Seven Year Hitch59%
This Means War61%
I Love You to Death64%
Killers59%
12 Dates of Christmas61%
The Good Witch's Garden74%
Sidelined: The QB and Me62%
Click & Collect66%