I wouldn't call the Match Game segment "brutal" like the poster above, but overall I agree that it's simply tough to execute in this format. In line with the SHEEP/PEEHS games: the contestant really wants to follow the herd as best as possible. However, if the contestant (or the panel) tends toward novel answers – perhaps because they're more funny or biting that way – then it hampers the game. So the PokerCast Match Game has largely consisted of PEEHS minds trying to play SHEEP.
By the way, part of the humor of the Match Game – not unlike Family Feud – is that the initial questions always come out as sounding suggestive. So whenever possible, they all need to get phrased (or rephrased) in that manner. (e.g. "Alec Torelli's recent angle-shooting allegations are hardly surprising. Back in high school, he was sent to the principal's office for not concealing his _____________.")
All this said, I found myself playing along with the show. Given my own responses, you can see why I enjoyed the segment more this time than before:
Anyway, you may consider pivoting this to something more Family Feud-ish, like PokerRoad Radio used to do. Shronk and Ali would poll a group of people – players, media members – then Sebok and Gavin would square off on the next episode.
Since you guys don't go on-site to tournaments like PRR did, just use the forum: Ross could poll a bunch of forum regs, then Adam and Terrence would battle wits. (This is why the SHEEP game reveal was much more enjoyable than any Match Game.)