1. I would definitely not choose the pillow talk option since you want to move forward not just have a conversation. I'd opt for the long drive conversation for this. As you know tired people do not have the best luck having big important conversations, and you don't want the day to wrap up with hurt feelings, on the off chance she has a reaction you do not expect.
2. Two months after Cookie's husband dies? That seems to not be the best timing. He died suddenly, not after a long illness, so that's going to take a hell of a toll. Each person has their own schedule to date again after that, but I would warn that I think so soon after has a greater likelihood to cause problems down the road, a chance that later she goes through a period of extreme guilt for jumping into a relationship so quickly.
I personally would also be somewhat repelled if somebody I saw as a friend and was interested in appeared to be being opportunistic - "your husband is dead, now we can be lovers!" Perhaps she has indicated she is ready or comfortable. Maybe you think that the comfort of your warm body is going to help deal with her grief, but that's not the healthiest kind to give right now IMO. Perhaps it is right for her, but I doubt you're being very objective right now, and she's in mourning, she cant be objective either.
3. Have you already actually already been physically involved in any way with Cookie during your marriage Wizzard? I get a feeling that perhaps you may have to some extent.
Happiness will never come to those who fail to appreciate what they already have.