It was Molly who earned a share of the best challenge award for the Zoomdweebies. A woman from another team had called the challenge line, offering a wager in which the payout was that a man from the team she was challenging take her out on a date. An answer from the challenged team was later played on air, and it was to point out that both the woman and the man she had challenged were both man were married... To other people.
Molly stepped up and responded to the challenge, saying that both of the wives need only spend one evening with her and they would both forego their husbands altogether. It was this, in conjunction with the other challenges, that was given the honor of Best Challenge for 2000.