- Early in the game, Erica mentions a rumor that the enigmatic bartender, Boss, wears his Sunglasses at Night to avoid a Woman Scorned. After sleeping with Catherine and finding out she's a Yandere, it cuts to Vincent wearing a similar pair of shades while on a date with Katherine, who points out they do a lackluster job of hiding his face.
- And towards the end of the game, when Boss is revealed to be Thomas Mutton and Vincent is demanding answers about the nightmares, he suddenly shouts "AND WHAT'S WITH THESE FUCKING SHADES? YOU ARE INDOORS!" and tears off his sunglasses. Mind you, he very quickly wishes he hadn't.
- When Vincent sees that all evidence of Catherine has been removed from his phone, he says something along the lines of, "It's all gone!" and Orlando takes it to mean he's out of toilet paper. The Mood Whiplash in the scene really needs to be seen to be appreciated.
- Earlier in the same scene, Vincent wonders if he's still dreaming. Orlando points out that Vincent would then be dreaming about two guys using the bathroom together.
- In Catherine's Good/True ending:
Nergal, Lord of the Netherworld: You promised you'd play video games with me tonight!
- "Top of the morning, kiddo." What really makes it is his sheep jammies.
- "Fucking blocks. I'm gonna climb the shit out of you!"
- During the credits in Katherine's true ending, the second picture has a series of cakes shaped like the blocks from the nightmares. But the funny part came from Vincent and Boss arguing with the latter giving the former a raspberry.◊
- Some of the text reply options can be pretty snicker worthy. For example, when responding to Katherine in an early part of a game, you can say you're too tired and your brain's full of stuff. Which results in "NOT ENOUGH THINKING POWER. SHUTTING DOWN." Then shortly after that, Catherine asks if you want pictures of her. If you're going for a chaos route, one of the answers is "PIX NAO PLZ".
- Catherine's true ending. Just Catherine's true ending. Especially when her father came. (Get your mind out of the gutter.) Also, the random succubus in the post-credits scene who falls over out of sheer lust.
- Many of the confessional questions are surprisingly funny.
- One is "What are your thoughts on underpants?" and the answers are, "It can go anywhere." or "You wear it... Under your pants."
- A noteworthy one near the end is "Would you marry the perfect...robot?" One of the answers is "Is it...fully functional?" It is worth nothing that there was a point where in the answer stats for this question, the "Is it...Fully Functional?" option just barely outnumbered the "I don't do Robots option", this means that quite a few people playing Catherine would do a robot...
- "This is the bathrooom ghoooooooossssttt!"
- A mixture of awesome and funny: the defeat of the Stage 3 boss (Immoral Beast). As the boss dissolves Vincent does his little victory dance and yells "Suck it!"
- When Toby finds out that Erica used to be male.
Toby: I want my V-Card back!!Erica: Sorry but once that hole's been punched, there's no getting it back!
- The freedom/neutral endings has Vincent arguing with Boss/Mutton over having Vincent's wish granted: Vincent wants Mutton to loan him some money...so Vincent can bet on a wrestling match. To go into detail, he was actually asking for the money ($500) to bet on a wrestling match because a god somehow wasn't able to give him 50 grand initially to go on a space trip, which, in itself, is a pretty hilarious prospect. Then in the True Freedom Ending, you really need to see the dumbfounded face on Mutton when he sees Vincent won the bet.
- Boss's hammy "FIFTY THOUSAND?!".
- There's loads of Black Comedy in Catherine's bad ending; after becoming manic after getting dumped by Catherine, Vincent runs outside to find her. He gets hit by a car. He then runs about inside the bar to let everyone know he was hit by a car.
- The fact that Boss/Mutton casually reveals that he was the one behind the nightmares and realizing that, that wasn't what Vincent was asking about is in itself hilarious, his face when he realizes this and him trying to backpedal.
- There's even a moment in the drink trivia that you get whenever you finish a drink in the Stray Sheep- the unfailingly calm, informative narrator has this to say after explaining what's in a Prairie Oyster cocktail. note
Narrator: Who thought this up in the first place?!
- One of the drink trivia for sake. It's referring to the old words that were used for sake. Same word can also be read as Masamune. "All that history, just for a pun?"