I think maybe they did have a meeting, but the bimbo is SO common, and he meets thousands of people, that she simply didn’t stand out in his memory. Even with those fat boobs sticking out the top of her shirt!
Wood is the type of lawyer that REALLY believes in his client's innocence before he accepts a case and he wouldn't permit Cain to dance around the truth in a presser (not that Cain would anyway).
As to other meetings 14 years ago, she was probably much younger and thinner than now. I saw her wedding photos the other day (they have since been scrubbed, I think) and she was quite beautiful back then.