I think I agree with most above about the first one, it was a weird question to throw in at that point. It does sound like you were unsure about the hair, so you were confirming. I have a friend at work who does this, who has been confronted by colleagues more than once about it, and she has a habit of talking about other people's appearances, which is generally speaking best to not do.
She said she does it for similar reasons as you've said here, but think about it - you're asking because YOU want to know they're happy; the question isn't about them, it's about you, which makes it quite a needy sort of question. And if you're talking about someone else's body and appearance really THEY need to lead the conversation, not you. As a role of thumb it's generally not ok to question other people about their physical appearances.
In this instance she obviously invited comment, but, I think we can presume that because she sent you a photo of herself with the hairdo that she was most likely happy with it, so the question was redundant - of course she was happy with it. Asking if she was happy with it was always likely to be misinterpreted. Don't ask the question next time - a nice, friendly comment would have ended after the first sentence, where you said you liked it. If she then wants to carry on with the conversation she can, it's her body, she only has to talk about it for the time that she wants to, she doesn't have to answer questions about it.
I don't agree with most here about the second comment, though - it was also a weird thing to say. The only time I can think of where that phraseology would have been appropriate would have been if he'd said "remember this place? I was so unhappy there" - "really? but you seemed so happy there". That's fine, that's normal. He says "remember this place?", and you say "yes, you seemed happy there" - weird. It's like you're saying he doesn't seem very happy now in comparison, and isn't that sad!
I think though that one you can just put down to a phrasing error though, once he's pointed it out, you say you didn't mean it like that, you both laugh because it was funny, move on.