100 Dates in Dallas Trailer: Jonathan Stoddard’s Rom-Com Previewed

Freestyle Digital Media will release the romantic comedy 100 Dates in Dallas on North American digital HD internet, cable, DVD, and satellite platforms on May 12, 2026. The film stars Jonathan Stoddard as a recently divorced man navigating the complexities of modern dating.

The film follows Jeff Brock, a former TV and movie actor, as he enters the world of post-divorce online dating. According to the official synopsis, his search for connection leads to “unhinged matches” and “shallow, booze-fueled dates,” resulting in a “comedic odyssey of awkward encounters and self-doubt.”

Stoddard is joined in the cast by Ashton Leigh (Lisa Frankenstein), Charlene Amoia (Scary Movie 6), Damian Turner (Landman), Gemma Berg (A Home for Christmas), and Amanda Button (Falling for a Killer).

Trailer Teases Comedic Misadventures

The trailer, which debuted exclusively on ComingSoon.net, introduces Stoddard’s character as he struggles to find meaningful connections with women he meets through dating apps. The preview showcases several humorous and chaotic situations Jeff encounters as he attempts to navigate the modern dating landscape.

Fred Olen Ray directed 100 Dates in Dallas, with a screenplay by Andrew Stevens. Stoddard also served as an executive producer, alongside Reed Hoelscher, Amanda Hölscher, Rick Moore, Alessandro Penazzi, and Sam Stevens. Stevens also produced the film.

“What attracted me to the project was the outrageousness and comedic eccentricities that people reveal on first dates, particularly when alcohol is involved,”

Fred Olen Ray

“100 Dates in Dallas is a depiction of actual online dating experiences, which range from the ridiculous to the absurd, as former actor, Jeff Brock, faces the trials and tribulations of dating in the digital age.”

Andrew Stevens

Stevens described the film as a reflection of “actual online dating experiences,” noting the “ridiculous to the absurd” nature of the encounters faced by the protagonist. Ray highlighted the comedic potential of the “outrageousness and comedic eccentricities” revealed during first dates, particularly when alcohol is involved.

100 Dates in Dallas is the latest release from Freestyle Digital Media, a distributor known for independent films across various genres. Jonathan Stoddard previously starred in Somewhere in Montana.

The film is scheduled for release on May 12, 2026, and will be available for rent or purchase on major digital platforms.