when dmming backfires

exploits of my Pathfinder group and the crazy shit my group manages to pull off no matter how high I make the checks. I am the DM. Our group consists of Diggs the half elf ranger. Jocelyn the elf rogue. Thetis the dragonborn barbarian. Theodore the dwarf fighter. Minty the gnome bard. Rowan the halfling cleric. Nameless half elf druid with velociraptor animal companion. And occasionally Steezius Maximus the human ranger.

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Me: “Under the archway you see a ruined doll with a melted face and stuffing spilling out of its side and next to it a fleet of melted tin soldiers.” Theodore the Fighter: “Im out. Bye guys. See you back at the tavern.” (Theodore DOES NOT like dolls at all irl.) Thetis the Barbarian: “Can I take the ruined doll?” Me: “Yes. You can take the ruined doll. What are you going to do with a ruined doll?” Thetis: *laughs* I dont know. I just wanted it. Rowan the Cleric: “It’s okay, she can give it to a ruined child later.”

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Minty: “I still have my two dead lizards.” Me: “What exactly do you plan on doing with those dead lizards?” Minty: “Well when Rowan learns Reanimate Dead I’ll have two live lizards.”

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This was the way our group started their journey.

Me: “You have all found yourselves in a tavern, for one reason or another, pondering the journey ahead of you. You glance around the room and notice each other, as well as the barkeep and a single barmaid.” Jocelyn the rogue: “Can I roll diplomacy to seduce the barmaid?” Me: “I…I suppose so.” Jocelyn: *rolls a 3* FUCK! Can I try again?“ Me: *shaking my head* "You can try again after a few in game hours I suppose.” *allotted time passes* Jocelyn: *rolls a 20* YES! Me: “Goddammit. You successfully seduce the barmaid and take her up to the vacant room in the tavern.” Minty the bard: “Can I sneak into the room?” Me: “Why would you do that?” Minty: “Iunno. Gnome. Mischief. Why not?” Me: “….roll a stealth check.” Minty: *rolls a 15 with plus 4 to stealth* Me: “….congratulations. You have successfully snuck into a room where two people are having sex. Now what?” Minty: “I hide under the bed.” Me: “Wha…why….to do what exactly?” Minty: “To wait.” Me: “……………………..”

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Our bard drew up a picture of her character for reference. She's one of my favorites because I have never run a campaign with a gnome bard before. It makes for some hilarious situations.

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Me: "You look around the room and notice two sleeping wolves." Diggs the ranger: "Bro, can I tame the wolf?" Me: "...do you have handle animal?" Diggs: "Yes. I do have handle animal." Arwyn the druid: "I have handle animal too." Me: "Okay, roll, but fair warning it's a high check. Asleep or not these wolves are hostile by nature." *Both PCs roll 20* Diggs: "Ayyyeeee!!" Arwyn: "Yes!" Me: "Son of bitch...." And that is how the group got pet wolves and avoided an encounter.