I flew with a guy like that once at my former employer. He kept telling me a story right up to 2000 ft AGL. He ended with, "What do you think?" I responded, "About what? The stupid story you just told me or landing gear up?" I then gave him my best deer in the headlights look. After that I just quit talking to him.

Then there was a guy that wouldn't shut up about the Lear and how great of an airplane it was because he flew it for 6 weeks at another company.

Good luck, it is a tought spot to be in.