Rick Glassman has built a strong following with his podcast, Take Your Shoes Off, where the stand-up comic sees interviewing celebrity guests as almost the perfect first date.

“There’s flirting involved. And flirting doesn’t have to have romantic interest. Flirting to me is similar to repartee – you nudge a little, you push a little and you let them do the same,” Glassman tells The Hollywood Reporter while bringing his solo show, Ricky’s on the Loose, to the Just For Laughs festival in Montreal.

He argues the best podcasts are where the vibe of two people meeting for the first time elicits light banter, jokes and playfulness and even subtle courting to see if his guests can work together on movies or TV series Glassman may have in the works.

His recent guest comedians, actors, directors and musicians include Alison Brie, Lisa Gilroy, Adam Ray making his 28th appearance, Nick Kroll and veteran showrunner Bill Lawrence. “Using play allows you to just be more present, and when you’re present, you’re not projecting what people are doing or why,” Glassman insisted.

Asked whether his first dates — sorry, podcast editions — should ideally end with a kiss of sorts gets Glassman to his stand-up act, where talk of dating etiquette and rules fill his comedic quiver. “When do you kiss? Do you ask? How do you ask? I remember I used to be scared of going on dates because, if I’m supposed to go in to kiss, what if I don’t want to yet? And what if they don’t want me to yet?” he ventures.