$S=\{1, 2, 3,\ldots, 1000\}$
$R=\{(x,y) \in S \times S: x \mid y\}$
My attempt:
Assume $xRy$ and $yRx$. Then $x=ym$ and $y=xn$ for $m$, $n$ in Natural numbers.
-So $x=xxn..$ that gets me nowhere.
-So $\left(\frac yn\right)=ym$, $\left(\frac1n\right)=m$. Then $x=\left(\frac yn\right)$ and $y=xn$. Then I just get $y=xn$ twice.
I think that I need to prove that $m = n$, but I get $m=\left(\frac1n\right)$. Any suggestions?
Since $x \sim y$ and $y \sim x$, we have (as you said) $x = ym$ and $y = xn$ for $n,m \in \Bbb N$.
Therefore we have, $$xy = xynm \implies 1 = nm \iff n = m = 1.$$
The result now follows.