Chris Ross Dating Tips emerged during the "Quiet Years" of Dollars & Donuts, serving as another creative lifeline while Daryl was bored.

The concept originated from a series of facetious, pseudo-scientific relationship advice posts Chris Ross had written on Facebook. Daryl Della saw the potential for a bite-sized sketch comedy format and adapted the posts into scripts, envisioning a ten-episode run.

Production was lean and efficient, characteristic of the era. Daryl and Becker Von Felsburg filmed Ross’s hosting segments against a green screen in Daryl’s garage, allowing them to drop him into increasingly ridiculous backgrounds. To flesh out the sketches, they recruited a roster of real and fake couples from their friend group, turning the series into a community effort.

Michael Martin’s involvement was minimal, reflecting the growing distance in the partnership. He participated in only two of the five completed episodes. However, the series produced a notable moment of friction-tinged praise: after filming the first episode, "I’m Not a Perfect Person," in which Daryl played the romantic lead opposite his wife Kirsten, Michael confessed he was "impressed" by Daryl’s acting, admitting, "I didn't know you could do that." For Daryl, the compliment felt like a classic backhanded slight—proof that after half of a decade of collaboration, his partner was still selling him short.

Only five of the planned ten episodes were completed. The remaining unproduced scripts didn't die; they evolved. When Dollars & Donuts pivoted to print media, Daryl adapted several of the lost episodes into one-page comic strips for Dollars & Donuts Showcase.

The most ambitious unfilmed script, Tip #10: "Baby’s Gotta Have," was intended to be the series finale. It featured a meta-breakdown where an actress rebels against Ross’s misogynistic advice, leading to a dark, cinematic montage of Ross destitute and drunk in the streets, muttering "I'm a scientist" to passersby. It remains one of the great "what ifs" of the web series era.