To recognize the formation of singularities (shocks) in your equation you may look for the intersection of characteristics curves. It is known that any smooth solution of your problem must be constant along characteristic curves, and if there is such an intersection, singularities arise.
Now, from your characteristic system, it can be seen that
$$ \frac{dx}{dy} = u^2, $$
due to the constancy of $u$ along characteristics, this means that the projection of the charactericts curves are straight lines with slope given by $1/u^2(x,0)$. Try to draw them out and use your initial condition to see if those lines intersect at some point.
On the other hand, to find a solution for your problem, you should bear in mind something which is known in the literature as the "jump condition" or "Rankine-Hugoniot condition". You can find information about it (together with nice examples) in Joel Smoller book : "Shock waves and reaction diffusion equations" Chapter 15. This condition allows you to give discontinuous solutions for your problem whenever an specific relation between the speed of propagation of the discontinuity and the values of the solution at both sides of the discontinuity is satisfied.
Roughly speaking, you must ensure that if $s$ is the speed of propagation of the discontinuity, then
$$ s[u]=[u^2],$$
where $[u]= u_r - u_l$, $[u^2] = u_r^2 - u_l^2 $ and $u_r$, $u_l$ are the values of $u$ at the right and left of the discontinuity respectively.