Unfortunately KDBCOM there's no analog sound output from the TiVo but your idea of changing to a flat screen is highly recommended. Not only to take advantage of High Def TV (not at all dissapointing) but on my TV there are numerous connections including anolog phono out, so connecting your headphones without disabling the TV sound isn't a problem. (adds to the sell to the wife as well!)
---------- Post added at 13:12 ---------- Previous post was at 12:57 ----------
Sorry KDBCOM I'm not stalking but have found the simplest and cheapest way to solve your problems, look at the two links!
http://www.maplin.co.uk/through-scar...nd-s-vhs-33041
http://www.amazon.co.uk/Female-3-5mm.../dp/B0029HQ132