Chris Ross Dating Tips came out of a stretch where Daryl was restless and bored, serving as another creative lifeline.
The concept began with a series of facetious, pseudo-scientific relationship advice posts Chris Ross had written on Facebook. Daryl saw an easy sketch format in them and started adapting the posts into short scripts, with the original plan calling for ten episodes.
Production was deliberately simple. Daryl and Becker Von Felsburg filmed Chris Ross’s hosting segments against a green screen in Daryl’s garage, then dropped him into a rotating series of increasingly ridiculous “professional” environments. The dramatizations were built around friends, couples, and whoever else could be convinced to participate.
Michael Martin’s involvement was limited. He only worked on two of the five finished episodes, which fit the broader uncertainty Daryl was feeling about the partnership at the time. The first episode also produced one of those compliments that managed to land sideways. After watching Daryl act opposite Kirsten, Michael told him he was “impressed” and admitted, “I didn’t know you could do that.” Daryl took it less as praise than as evidence that, after years of working together, Michael was still underestimating him.
Only five of the planned ten episodes were completed. The unused material did not disappear. When Dollars & Donuts later moved into comics, several of the unproduced ideas were reworked into one-page Chris Ross Dating Tips strips for Dollars & Donuts Showcase.
The biggest casualty was Tip #10: “Baby’s Gotta Have,” intended as the finale. The script broke the format apart completely, with an actress finally rebelling against Chris Ross’s advice and sending the series into a much darker ending. Ross winds up destitute, drunk, and wandering the streets, still insisting to strangers that he is a scientist.
