If you’re hitting it off you still need to send him a signal that you want him to ask you out because he may think you are just being friendly or kind. A lot of guys and woman in our age group that are widowed or divorced are somewhat insecure when it comes to asking a woman out. We are all vulnerable and don’t want to set our self up for disappointment and rejection. You may need to make it very clear your interested in spending an afternoon or evening doing something you both enjoy whether it’s a lunch or dinner, movie or theater. Its perfectly respectable for you to say (you) “I have a ticket to a play and I don’t want to go alone, would you care to join me”? Or (you) “I was thinking of trying this new restaurant have you been there”? He may jump right in and say (him) “No I haven’t would you like to join me”? All you need to do is find a way to break the ice.