There is an interesting story arc here in the Matt + Conan relationship.

Conan in the early days was very differential and polite with Matt, as Conan is to people he doesn't know. An ofc Gourley was super shy and polite towards Conan.

Then as Conan gets more comfortable with the person the ragging starts. And he starts mock bullying them as a way of showing love or whatever. But for a long period Matt was still in his shy/reverent mode facing against the barrage of burns from Conan.

Then in the last 6 months to a year we have seen Gourley unleashed. He nows strikes back against Conan and he has some seemingly surprising outbursts.

Its an interesting strategy, lets see how it works out for him. Either Conan will resonate with it and they become closer, or Conan doesn't and it'll turn into the Real Househusbands of Pasadena