Hi Roohi,
I would wait, but not for long. Meaning, the next time (for instance) you two plan to meet some of his old friends (one or two he had had flirtations with) then you can say, “Oh by the way, now that we’re alone in the car together, tell me about your relationship with them. You never bring your past up? Why do you think that is, handsome?” Be light hearted when you bring it up, never confrontational!
With DH I would say, “You were kind of a playboy, weren’t you?”
He would blush, smile, look uncomfortable, but, being a gentleman, would say nothing about his old fan club.
It could be a generational thing: Young men say everything, older men say not a lot!
That is what you are worried about. Talk, check in, go to one of those couples retreats (for fun mostly!) and then with help you can tease it out of him and calm your mind.
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