Your mention of hiring an escort was part of sharing your story after your wife’s passing, not something you meant to linger on. So it makes sense that his repeated references to it felt off, especially since they seemed to overshadow the rest of your connection and left you uncomfortable.
People react to this kind of information differently. His comments might have come from curiosity, insecurity, or even judgment but it’s hard to know without more context. Sometimes when something is outside someone’s own experience, they fixate on it, like with him saying: “never having hired anyone.” The fact that he brought it up during and after intimate moments probably made it feel even more intrusive.
If those remarks felt like a red flag, it’s completely fine to trust your gut and reconsider whether you want to see him again. Ask yourself whether his tone came across as judgmental or just awkward curiosity, and whether talking it through could help clear things up.
For what it’s worth, I don’t usually mention hiring unless someone asks me directly. It’s not exactly common small talk material.