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.
You’ve spent some time talking with someone and you think you like her. Everyone wants to be liked and make a good impression but don’t overdo it. When you meet someone you like and feel you want to spend a little one-on-one time with her it’s only natural to put your best foot forward and you should. But first step back and ask your self why you are attracted to her. Are you both on the same wavelength? Do you like the same things? You should not tell her things you think she wants to hear just so you can impress her. There’s nothing worse than after you have won her over and she figures out that you were not upfront about your likes and dislikes this will end a relationship and it will not be fun along the way. There is nothing more rewarding than getting together to do something you both enjoy.