How to be a Gentleman chronicles the life of Andrew (David Hornsby) and follows him as his boss (Dave Foley) at the magazine he works for informs him that the publication is going in a newer, younger direction, and he therefore must change his eponymous column, because it's too stuffy and it's not cool or young enough (which is kind of a sad statement on society, but anyway).

Andrew is reluctant at first to change it. At his birthday dinner soon after, which only his mother, sister and brother-in-law attend, we learn he has no friends, his girlfriend left him because he wasn't assertive enough, and that his mother only has peripheral vision. He's also given a gift certificate from his sister to a gym. There, Andrew runs into Bert (Kevin Dillon), an old high-school bully. Oddly, Andrew isn't phased by running into him, but doesn't want the training session with Bert, who is a macho moron.

When Andrew is threatened with the loss of his job, he swiftly changes his mind and comes up with the idea to enlist Bert as a resource as to what the younger general public would find 'cool'. Bert accepts and soon sees this as a chance to teach Andrew how to be a 'real man'. Bert encourages (more like pushes) Andrew to ask out his cute neighbor who's been flirting with him, and she says 'yes'. But on the date, Andrew leaves for a few moments only to come back to find her making out with her ex-boyfriend (who is the owner of the restaurant).

Instead of meekly leaving or conceding defeat, Andrew is motivated by his new-found 'manliness' to bitch-slap the guy, which is pretty funny. He also encourages Mike, his brother-in-law, to be more assertive with his wife, who's been watching her on a date with a co-worker. At the end of the first episode, we learn that Mike's also hired Bert as a trainer.

The supporting cast includes Andrew's mom, Diane, played by funny character actress Nancy Lenehan, his annoying and judgmental sister Janet, played by Mary Lynn Rajskub and maybe the funniest character, Mike, his British brother-in-law, played by Rhys Darby. The show has funny lines. But honestly, the sitcom's canned laughter is quite annoying. Nevertheless, it juxtaposes a total 'gentleman', Andrew, who always does what's right and proper with a total dude, Bert, a guy's guy, and it's amusing to watch the two actors play off each other.