Day Drinking with Mom celebrates teachers – even the bad ones – this Wednesday

Comedian Wendy Maybury might be flunking kindergarten this year.

Comedian Wendy Maybury might be flunking kindergarten this year. Provided

Wendy Maybury sucks at teaching. But for the past few months, she’s had no choice but to fill the role of kindergarten teacher for her son.

“First of all, I can’t get my son to wear pants. And he’ll probably never be an obedient student ever again,” she laughs. “The veil has been ripped off. He knows there’s no permanent record and that none of this really matters. I called the principal and said, ‘I suck at this.’ And she told me, ‘We’ll catch him up next year.’”

This Wednesday Maybury, along with co-host Karen Pickering, will put their real talents to use for a virtual teacher appreciation edition of their monthly standup showcase, Day Drinking with Mom.

The show has been around since 2017 and features a rotating cast of standups talking about all things parenting. This month, teacher/comedian Devin Siebold is headlining the show, talking about the joys and pains of teaching kids – whether they belong to you or not. Siebold isn’t just a big deal with teachers, as he has more than 80 million YouTube views and regularly headlines comedy clubs (remember those?) all over the country.

Best of all, the show is a chance for teachers to come together for an end-of-the-year celebration that they might not have had otherwise.

“One principal from around here bought 10 tickets and gave them to his staff,” Maybury says. “We’ve had a lot of groups of teachers buy tickets so that they can have their end-of-the-year last hurrah together. I’ve had teachers tell me they’re planning to watch on their computers and be on FaceTime with each other, so they can laugh together.”

Wendy Maybury, Devin Siebold

Wendy Maybury, Devin Siebold Promo shots

Tickets for the virtual show are just $5, but Maybury says that the generosity of comedy fans has been overwhelming.

“We listed the ticket prices as $5 to $25, and all the money goes to the comedians,” she explains. “We’ve seen that people who can afford it didn’t mind giving extra, which is really great for all of us.”

And since finding the time to watch a full comedy show can be hard when you’re in parent-mode, a recording of the show will be available to all who purchase it for 48 hours after.

Aside from being able to keep doing comedy, another bonus of moving Day Drinking with Mom online is that Maybury’s been able to connect with people who otherwise may not have the chance to see her live.

“I’ve lived in nine states as an adult,” she says. “I know a lot of people who have said, ‘When you come to -- some small town that I’ll never get to -- let me know and I’ll bring all my friends to see you!’ So now I can just have them buy a ticket and they can show up and say hi.”

While the show itself should be really funny, Maybury says that it might not measure up to the accidental comedy of her newfound teacher role.

“Asking a comedian to home-school her kindergartener is Romper Room central over here. I think we’re both going to have trouble when we need to go back to reality.”


Day Drinking with Mom with headliner Devin Siebold
8 p.m. Wednesday, May 27
Click here for tickets