Here's one:
[tex]\begin{bmatrix}1 & 1 \\ 0 & 1\end{bmatrix}[/tex]
Happy?
If a 2 by 2 matrix cannot be diagonalized, it must have a single eigenvalue and it can be put into "Jordan Normal Form",
[tex]\begin{bmatrix}x & 1 \\ 0 & x\end{bmatrix}[/tex]
where "x" is that single eigenvalue.
Now, if
[tex]\begin{bmatrix}a & b \\ c & d \end{bmatrix}[/tex]
is a "square root" for that matrix, we must have
[tex]\begin{bmatrix}a & b \\ c & d \end{bmatrix}\begin{bmatrix}a & b \\ c & d \end{bmatrix}= \begin{bmatrix}a^2+ bc & ab+ bd \\ ac+ dc & bc+ d^2\end{bmatrix}= \begin{bmatrix}x & 1 \\ 0 & x\end{bmatrix}[/tex]
That is, we must have [itex]a^2+ bc= x[/itex], [itex]ab+ bd= 1[/itex], [itex]ac+ dc= 0[/itex], and [itex]bc+ d^2= x[/itex].
From [itex]ac+ dc= c(a+ d)= 0[/itex] we must have either c=0 or a+ d= 0. But a+ d= 0 cannot satisfy [itex]ab+ bd= b(a+ d)= 1[/itex] so we must have c= 0.
Then [itex]a^2+ bc= a^2= x[/itex] and [itex]bc+ d^2= d^2= x[/itex].
Since [itex]a^2= d^2= x[/itex] we must have either a= d or a= -d. If a= -d then ab+ db= b(a+d)= 0 so that ab+ db= 1 is impossible. If a= d, then ab+ db= 2ab= 1 so that b= 1/(2a). That is, the matrix
[tex]\begin{bmatrix}x & 1 \\ 0 & x\end{bmatrix}[/tex]
has two square roots:
[tex]\begin{bmatrix}\sqrt{x} & \frac{1}{2\sqrt{x}} \\ 0 & \sqrt{x}\end{bmatrix}[/tex]
and
[tex]\begin{bmatrix}-\sqrt{x} & -\frac{1}{2\sqrt{x}} \\ 0 & -\sqrt{x}\end{bmatrix}[/tex]