How can I tell where this is headed?

I’ve known a guy for about nine years, I’ve had a crush on him for about that long but always thought he wasn’t really interested (the only reason why we met was because my parents were trying to hook us up-they’re still hoping actually). Since meeting him I’ve been in a four year marriage, lived in another country for two of those years, have gotten divorced and am now living in a large city for now two years. Obviously I’ve been through some changes since we first met each other. He has also been through some changes in his life as well. We keep in touch but it’s only a conversation here and there every few months….most of the reason for the time between talking seems to be because one of us is always in a relationship or dating someone (he talks to my parents on occasion and I assume they tell him what I’ve been up to). Or just focusing on things in our own life He seems interested to a point but not quite sure at the same time. I tried to see how interested he was after my divorce was finalized and he agreed to a lunch but that was all. I later found out he was having an affair with a woman we were currently working with at the time I tried dating him. Because the affair was a secret, obviously lol, he told me that he had feelings for me and liked me a lot but didn’t want to get involved because he considered his relationship with my family valuable enough to not risk ruining it. I can agree with this, however, I’m not sure I understand why he’ll show interest sometimes if he doesn’t want to risk his reputation with my family? Or is this all just wishful thinking on my part?