Hi longboarder. I find it is difficult to know which way to go. Of the two women you mention, I like the idea of the safer Crissy than the fiery Annette. Of course it is totally your decision and need to evaluate how you feel. To me over 50 is more a time of relationships. It may be you are more a caregiver or just a pal to Crissy than you want to be. But sometimes being needed can be more important than being wanted. That is a highly personal decision.
Have you ever discussed with Crissy about if she has any thoughts of being closer to someone or what she sees in her future? She may not be the flame of your life, but she sounds like a good buddy for someone over 50 with less drive to express.
Glad you have joined our community. Many people here at PC find they can share these feelings and what they are going through with the confidence that people go through similar things and can empathize. So many forums are offered as well as Chatrooms (after you have 5 posts or comments on others posts). Depression chat meets on Thursday night at 9pm EST and Anxiety Wednesday at 8PM.
You can also be an active member in other ways like supporting others in their questions, reading articles and posts
http://forums.psychcentral.com that are applicable to your area of concern.
Please feel free to private message me or any of the Community Liaisons by left clicking on the name in blue to the left of their post) for questions or just to share.