Make it clear that your supervisor is trapped in your conversation, not the other way around. When you have to be professional, be professional. But the rest of the time, talk about the dirt between the planks of wood at home. Talk about the sedimentation process of your aquarium's gravel. Basically the moste innate and boring topics that no normal human would bring up, repeated ad nauseam.

Make sure to take long pauses just to resume talking. Remember to take your time while monopolizing the conversation trying to find a word your forgot about.

Remember to mispronounce every word, especially if he corrects you but be sure to keep plausible deniability just in case he accuses you of doing it on purpose.

Remember to always blame everything on something that has no connection to it.

Remember to enrich your diet with garlic, to use terrible flavored candy or just skipping a meal for extra word flavor, if you can take the reputation hit.

Remember the magical phrase: "that reminds me of" and all variants of it.

Remember to look into his eyes, and to alternate between them and another part of his face as if something is wrong with it. Keep affirming that everything is alright while staring at that part.

Change the subject. All the time.

Have terribly strong inconsequential opinions and remind about them all the time.

Monopolize the conversation, but make him want to cut you off or talk. I

IMPORTANT : If the other party is silent, state how comfortable you are with this silent friendship.