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Henry Spencer loves his son, let there be no doubt about that. He might not always like him, exactly, and hardly ever understands him, but he does love him. He might not be happy with the choices Shawn's made, but he has grudgingly accepted that his son won't ever be a cop, or even a real PI - which is just one step above criminals anyway - and he's mostly settled in to the idea that Shawn Spencer is a psychic detective. Well, not psychic, but he figures that whatever provides Shawn with a steady paycheck and keeps him (mostly) out of trouble, Henry can't complain about. Too much.
He tries not to interfere too much with Shawn's life, tries to stand back and let Shawn make his own decisions, but sometimes that's damn hard to do, because he keeps screwing those decisions up. Like now, when he’s going on a second date with that girl from high school, instead of getting his head out of his ass and ask Detective O'Hara out.
Shawn might be the one with the hyperawareness and the eidetic memory, but Henry notices a thing or two himself. Like the way Shawn's eyes flicker nervously when Juliet’s name comes up, or how Gus snorts when Shawn talks about going on second or third dates with girls who aren't her, or the way the detective seems to both seek out and avoid Shawn. Henry knows that Shawn flirts with anything in heels - or flats, for that matter - but he’s got a feeling this thing might be for real.
He likes the idea of Shawn and the detective. He won’t ever tell Shawn (he’s got a feeling that his approval would somehow taint the whole thing for his idiot son), but he’s actually thrilled. If he couldn’t get a cop for a son, he thinks it’s close enough to get one for a daughter-in-law, if only his son could just... get on with it, and manage to win Juliet over in the process. He doesn’t blame Juliet for holding off, Shawn can be a walking disaster at times. At the bottom though, he’s got a good heart, and Henry thinks Juliet might be more easily swayed if, instead of all of Shawn’s usual theatrics, she got a glimpse of that.