Anyone else experience something like this in the midst of their lives in crazy times?
The last time I "seriously" dated was decades ago. I've been surprised most women I meet aren't looking for marriage, kids, or a commitment to forever. They're just looking for attraction, chemistry, and a relationship that's an asset rather than a liability.
Personally, I'm 40s and have dated women my age +/- 8yrs. I met a woman +10yrs who I'm clicking with. Yes, an age starting with a 5!!! I'm being silly, of course, but her son is the same age as mine and her career is in a similar place.
Why shouldn't the 30s guy court a 50s lady if he finds her attractive? You asked what HE is looking for. What are YOU open to? You get to set the tone and pace. E.g., are your dates at a public walk, a picnic, a lunch--or a darkened theater--or dinner at his place? I encourage being intentional and no regrets. (: