Yes, but in the right context. Women are looking for both strength and vulnerability, and exposing yourself a little can go a long way towards building an initial connection. Here’s the only guideline – you’ve got to get in-and-out on this topic, tap it’s power and quickly move on. Use
your ‘situation’ as a lead in to a compliment., for example, ‘this is my first date in 20 years, but the second I saw your smile any little nervousness just washed away’. If she asks a follow on question about your past, hit it with ‘that is old water under the bridge, tonight is about ‘what’s next’” and get off the topic.
There is no reason to be anxious about being back-in-the-pool, whether you’ve dated or not in the past two decades, you have improved your skills in meeting new people and making a connection..
If you feel you must discuss your new dating status, use it as an on-ramp to a compliment.