I just finished a Boston Legal rewatch.
As I was watching, I came to the conclusion that I don't think Alan's late wife was younger or the same age as him. I think she was older. By at least a decade.
"Creativity, desire, zealotry, a gorgeous clavicle, healthy lack of inhibition" is how he described her and that can apply to women of any age. He's always been attracted to older women.
He says "she began to know me too well." Maybe his wife had been with men previously just like Alan. Whether that be an ex-boyfriend or even an ex-husband along the way.
I don't know where in the timeline she fits though. Just after he graduated law school? Between Howard & Brock and Carruthers Abbott? I think they were married for at least a few years.
I did also have a passing thought that maybe she was the "someone very dear to me died with Alzheimer’s" that he mentioned to Denny in The Practice. Denny called back to that conversation (not that line though) in BL, so I don't consider it a throwaway line. But early onset Alzheimer's wouldn't be out of the realm of possibility if she was older than him. It just would contradict that she knew him too well though.













