They were engaged during the MS Bob project - I was there when she was showing off the ring. Strangely, we discussed bungee jumping. I used to make the joke that she lost use of her left arm having to carry that rock around all the time.
I've admitted it before, I worked on Bob.
Bob was never marketed to IT buying groups. It was aimed at your typical consumer who was afraid of a PC. That's why the apps were: List maker (excel with only one column), Letter Writer (Write+/-), Something like Publisher, but not and Mail which instead of folders had an old fashioned letter desk interface where you composed and organized your mail.
Bob was for your grandmother, your non-technical Mom / Dad, etc. The problem is that it only worked well on a P90, which was a $5k computer at the time which no grandmother was going to buy. We wrote it in VB as it was a Melinda Gates / Karen Fries project and Bill's obsession was VB for reasons. VB was never able at that time to achieve the visual performance required to make Bob work on a true consumer class PC - a 486/66 or actually lower at the time.
We brought in the compiler team to try to optimize the performance without any real luck.
IIRC, when it shipped it took 17 seconds to launch on a P90 and I could crash it in 3 clicks.