I am trying to show that for any Lebesgue measurable set of finite positive measure $E$, the characteristic function $\chi_E$ is not in $H^{\frac{1}{2}}(\mathbb{R}^n)$. I found somewhere that it would be enough to show instead that
$$ \int_{\mathbb{R}^n} \int_{\mathbb{R}^n} \frac{\vert \chi_E(x)-\chi_E(y) \vert^2}{\Vert x-y \Vert^{n+1}} dx dy $$
is infinite. I think that the numerator is simply the sum
$$ \chi_{E\times E^c}(x,y)+\chi_{E^c\times E}(x,y) $$ which simplifies the problem to showing that
$$ \int_{E} \int_{E^c} \frac{1}{\Vert x-y \Vert^{n+1}} dx dy + \int_{E^c} \int_{E} \frac{1}{\Vert x-y \Vert^{n+1}} dx dy $$
is infinite, and using Fubini, I think it is enough to show that the first term is infinite. However I am having trouble trying to simplify it further, and think that I should eventually use an integral of the form $\int_1^\infty \frac{1}{r^p}dr$ somehow.
I would appreciate any hints or helpful remarks, including those telling me that this attempt is inherently flawed.

So with your method, the difficulty is the fact that you have no knowledge of the set $E$ at which the singularity occurs. However, the $H^{1/2}$ seminorm (the quantity you are trying to compute, that I will denote $\|\cdot\|_{\dot{H}^{1/2}}$) decreases when one takes a symmetric decreasing rearrangement (see e.g. Lemma 7.17 in the book Analysis by Lieb & Loss). Therefore, taking the ball $B$ centered in $0$ with the same measure as $E$, we have that $$ \|\chi_E\|_{\dot{H}^{1/2}} \geq \|\chi_B\|_{\dot{H}^{1/2}} $$ From there, one way could be to use the Fourier transform definition of $H^{1/2}$ and the exact Fourier transform of $\chi_B$ (see e.g. Fourier transform of the indicator of the unit ball). This gives us $$ \|\chi_B\|_{\dot{H}^{1/2}} = \int_{\mathbb{R}^n} |J_{n/2}(|x|)|^2 \,|x|^{1-n}\,\mathrm{d}x = C_d\int_0^\infty |J_{n/2}(r)|^2\,\mathrm{d}x $$ which is infinite since (see https://en.wikipedia.org/wiki/Bessel_function) $$ J_{n/2}(r) = (\tfrac{2}{πr})^{1/2} \cos(r-\tfrac{(n+1)\pi}{4}) + O_{r\to\infty}(\tfrac{1}{r}) $$ Therefore your integral (i.e. the seminorm) is infinite and thus $\chi_E$ is not in $H^{1/2}$.
Remark: If you want to use your computation, from my first equation you can now restrict to a ball and you have $$ \|\chi_B\|_{\dot{H}^{1/2}} = 2\int_{B} \int_{B^c} \frac{1}{|x-y |^{n+1}} \,\mathrm{d}x \,\mathrm{d}y $$ which might be easier to estimate. I suppose one can restrict this integral on a neighborhood of a point of the sphere and then say that the ball is flat near this point to also get estimates on why this integral is infinite?