I didn’t remember the first time that Jim McDonald performed on Letterman, but sure enough, the Internet tells me it was about four years ago. McDonald also has done Ferguson’s show twice, and been around long enough to have TV credits on the old A&E shows from Caroline’s and The Improv.

His style and delivery reminds me a bit of Brian Kiley.

In this set from Thursday’s episode of Late Show with David Letterman, you’ll find out what McDonald thinks about relationships and why he’s still single. Roll the clip.