I have had various friends over the years who were clever and funny but relentlessly cynical. I found spending time with them to be quite enjoyable and amusing,

I have had various friends over the years who were clever and funny but relentlessly cynical. I found spending time with them to be quite enjoyable and amusing, but only for limited amounts of time, occasionally. With too much exposure their cynicism just got tedious. The edgy jokes lost their edge. The worldview seemed more defeatist-for-its-own-sake than inherently more perceptive than alternatives. Making fun of all the clueless optimistic imbeciles out there started to seem pointlessly mean. The conversations started to get boring and repetitive. YMMV.