Josh is excited to get to know his new Irish bartender friend. She thinks they should get together the next day when she's finished early so he doesn't compromise his liver or her tips.
Diana reminds Charles that the company picnic is at his house the following week. She complicates matters when she wonders if Pauline will be there.
Charles' friend asks what's up with Pauline, too, suggesting he'd be pleased if his wife left for a year and came back a changed woman. Do none of these people know Charles?
Charles lets his friend know that it's not as simple as taking Pauline back into his life because there's someone else. He's not ready to talk about it yet, though.
In the meantime, Pauline tries to shakedown Liza about who Charles might be seeing putting Liza into a very uncomfortable place.
A couple of Japanese people are looking at the tattoo shop.
Kelsey suggests Josh design his own coloring book. Great! He can get a $10,000 up front thing. Better!
Josh and Claire go to a Mexican restaurant, but he discovers she's a jalapeno virgin. She goes for the hottest of the hot and cannot believe it's in her mouth. She seems like a lot of fun.
Back at Josh's place, they're making out, and she puts her hands down his pants only to reveal PEPPER DICK!! That soon turns into yogurt dick, and she says it's the best first date he's ever head.
Kelsey invites Josh and Claire to the company picnic to shake Charles' hand. At least Josh is truthful with Claire, even down to the possible proposal.
When Josh hears tattoos give the adult coloring book a millennial twist, he can barely hold himself in.
Of course, Pauline is asking whether she looks sexy or not and the two begin talking about a lot of things. Diana breaks in so she can assure Pauline she and Charles are not a thing.
Liza heads out to officiate the sack race, and when Charles and Josh get tangled up in their sacks and fall to the ground, Charles helps us Josh and then Josh slugs him in the face.
Kelsey cannot believe that just happened and tells Josh he just lost $10k. He knows, but it felt fantastic.
Liza makes sure Charles is OK, but when he says his feelings haven't changed, she says everything has changed and walks out of the swim house.
The situation only brings Claire and Josh closer together.
Kelsey gets the truth out of Liza and wants to make sure Liza doesn't take their relationship any further.