I am an 81 year old widower who lost my wife of 20 years just 5 months ago. She always told me to find a companion (she had a stroke), if anything happened to her. I do feel guilty about dating, but the loneliness gets to me sometimes. I have taken ladies to lunch and play bridge twice a week, but find older women kind of defensive, and the pretty and smart ones very independent at our age. My problem is that I hit on the younger ones (like in their 60's) and they don't like the age difference. I'm just looking for someone to buddy around with, but not having much luck.
Your wife must have been a loving, kind and generous woman to remind you that human connection and romance, at any age, should always be part of your life. In her memory, you must allow yourself to feel good about reaching out to forge new friendships, or romantic connections. This is what she wanted for you. I'm guessing if things had gone the other way and she had been left without you, your wishes for her would have been similar. It sounds to me like you've known great love in your lifetime.
I understand the guilt though. I actually cried when I realized during my own separation that I might one day love someone again. They were tears of both regret and joy, as well as grief and possibility, all mixed up in an emotional mess, which is exactly how I felt. The guilt is normal. It will pass.
Moving on is a process that begins with a decision to just say "yes" to the possibility of someone. Perhaps a somewhat shut down woman of your own age might actually open up with a little attention and affection. I've seen it happen. There's noting wrong with dating down in terms of age, but if you're reaching too low and finding younger women aren't interested in someone your age, you may need to adjust your strategy.
There are Meetup groups for older singles in certain areas. These people may get together to go on an easy hike, attend an art gallery opening or just grab lunch. It's not quite dating, but sparks do fly for some people, and it gets you out in a community of single peers. If there isn't a Meetup group in your area, you can start one!
Have you tried online dating? I would suggest a site with high behavior standards like Match. I spent ten years working at Match and saw countless love stories change the lives of older singles. One of my favorite success love stories at Match came in from an older man who was writing in to share his happiness. He wrote that "If a legally blind, bald, one-legged old man can find love online, than anyone can. " I believe that with all my heart.
Travis, you're going to be fine. Try dating women in their 70's, if women in their 60's feel you are too old. Go out and have fun with women. Volunteer in your community. Walk someone's dogs. Try online dating. Put yourself out in the world and be open to friendships with women you encounter. Falling in love with a friend is a great happy ending.
Stay in touch and let me know how it goes.