I'll just give the idea for weak differentiability of functions $u: \Bbb R \longrightarrow \Bbb R$; the ideas extend to more general cases without too much effort.
If a function $u: \Bbb R \longrightarrow \Bbb R$ is differentiable, then by integration by parts, we know that for any differentiable function $\phi: \Bbb R \longrightarrow \Bbb R$ such that $\phi(x) = 0$ for $|x|$ large (i.e. $\phi$ is zero outside a bounded subset of the real line) the following holds:
$$\int_{-\infty}^\infty u \phi' ~dx = \left. u\phi \right|_{-\infty}^\infty - \int_{-\infty}^\infty u' \phi ~dx = - \int_{-\infty}^\infty u' \phi ~dx.$$
The idea behind weakly differentiable functions is that we ask for this integration by parts formula to hold, but we don't assume that $u$ actually has a derivative in the normal sense.
To be precise, a function $u: \Bbb R \longrightarrow \Bbb R$ is weakly differentiable with weak derivative $v$ if there exists a function $v: \Bbb R \longrightarrow \Bbb R$ such that
$$\int_{-\infty}^\infty u \phi' ~dx = - \int_{-\infty}^\infty v \phi ~dx$$
for all smooth functions $\phi: \Bbb R \longrightarrow \Bbb R$ that vanish outside some bounded set.
Functions which are not differentiable can still be weakly differentiable. For example,
$$u(x) = |x|$$
is not differentiable because of the corner at $x = 0$, but it does have weak derivative
$$v(x) = \begin{cases} -1, & x < 0, \\ 0, & x = 0, \\ 1, & x > 0, \end{cases}$$
as can easily be checked (note that we should consider integration here as Lebesgue integration).
Weakly differentiable functions can be very badly behaved. For example, one can construct a weakly differentiable function on the unit ball $B(0,1) \subset \Bbb R^n$ that is unbounded on every open subset of $B(0,1)$. On the other hand, functions with "too big" of a jump discontinuity, such as the weak derivative of $|x|$ above, are not weakly differentiable.