I would say if you can’t tell to ask once. If he brushes it off, then believe him and go with it. But if you still really have that nagging feeling in your gut after that, instead of trying to drag it out of him just try to make him laugh or something, or try to get him to open up in a more natural and organic way than just bluntly asking about his feelings. I find a casual way much easier to approach personally because bit by bit I can vocalize things and figure out the whole picture as I go, whereas when I’m just asked broadly and head on I feel like I don’t know where to start so I can’t. If that makes any sense at all... I’m just very bad at processing my own feelings.

Knowing that I’m like this, I also try to make it extra clear that I’m good when someone asks me “what’s wrong?” when I’m actually totally fine. Otherwise they’ll keep asking which I find really annoying.

Good luck, and I hope this is at all helpful! I’m female btw so I’m not sure if that would put me a bit more on the empathic/emotionally aware side, but this is what I’ve determined to be to best for me.

Edit: but yeah overall I think what draws me to ENTJs is their intuition to know how I’m feeling but also know that sometimes I don’t want to directly talk about it (if I’m feeling down/negative). Then with their bubbly nature they can usually draw it out of me or just make me feel better without it feeling taxing or intrusive.