Let $H$ be the upper half-plane in $\mathbb{R}^2$. How does the following expression $$ds^2= \frac{dx^2+dy^2}{y^2}$$ specify a Riemannian metric on $H$?
I don't understand what the expression means. If the $y^2$ wasn't there, then $g=dx^2+dy^2=dx\otimes dx+dy\otimes dy$ is the standard metric. This does make sense to me: at every point it associates the standard inner product. But the above expression is not even symmetric in $x,y$ so it isn't meant to be read the same way, but I don't know how to make sense of it.
As you note, $dx^2 + dy^2$ means $dx \otimes dx + dy \otimes dy$. The expression means exactly what it says: you divide this tensor by $y^2$. It may help to write it as
$$ \frac{1}{y^2} dx \otimes dx + \frac{1}{y^2} dy \otimes dy $$
While a metric needs to be symmetric, there is no reason it needs to be symmetric under swapping $x$ and $y$. Let me add color to help you through your confusion: the tensor we define is
$$ g = \frac{1}{y^2} \color{blue}{dx} \otimes \color{red}{dx} + \frac{1}{y^2} \color{blue}{dy} \otimes \color{red}{dy} $$
The requirement that $g$ be symmetric means that $g$ needs to be equal to
$$ \frac{1}{y^2} \color{red}{dx} \otimes \color{blue}{dx} + \frac{1}{y^2} \color{red}{dy} \otimes \color{blue}{dy} $$
and it is, because the color is just notation and isn't part of the metric.
An example of a tensor that isn't symmetric is $dx \otimes dy$.