Let $\omega_1=\sum_{i=1}^2\sum_{j=1}^2a_{ij}dx_idx_j$,
$\omega_2=\sum_{i=1}^4\sum_{j=1}^4a_{ij}dx_idx_j$,
$\omega_3=\sum_{i=1}^N\sum_{j=1}^Na_{ij}dx_idx_j$.
In each case, I'd like to find $\omega\wedge\omega$ and find the relationship between $\omega\wedge\omega$ and the matrix with entries $a_{ij}$.
I think $\omega_1\wedge\omega_1=0$ because each term will will look like $dx_1dx_2dx_1dx_2$, and each of these is zero because $dx\wedge dx=0$.
For $\omega_2\wedge\omega_2$, the only nonzero terms are permutations of $dx_1dx_2dx_3dx_4$. There are twelve of these, and after rearranging, you get something like $fdx_1dx_2dx_3dx_4$, but what is an easy way to see what $f$ is and its relation to the matrix with entries $a_{ij}$?
and $\omega_n\wedge\omega_n$?
Take $$ \omega=\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k $$ for instance. Note that $j$ and $k$ are merely indices for summation. Thus by exchanging all $j$'s and $k$'s, we have $$ \omega=\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k=\sum_{j,k=1}^Na_{kj}{\rm d}x_k\wedge{\rm d}x_j. $$ Yet due to the asymmetry of the wedge product, $$ {\rm d}x_k\wedge{\rm d}x_j=-{\rm d}x_j\wedge{\rm d}x_k $$ holds unconditionally. Therefore, the expression goes that $$ \omega=\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k=\sum_{j,k=1}^Na_{kj}{\rm d}x_k\wedge{\rm d}x_j=\sum_{j,k=1}^N\left(-a_{kj}\right){\rm d}x_j\wedge{\rm d}x_k. $$ Due to the equality of the second and the last term, we have \begin{align} \omega&=\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k=\sum_{j,k=1}^N\left(-a_{kj}\right){\rm d}x_j\wedge{\rm d}x_k\\ &=\frac{1}{2}\left(\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k+\sum_{j,k=1}^N\left(-a_{kj}\right){\rm d}x_j\wedge{\rm d}x_k\right)\\ &=\sum_{j,k=1}^N\frac{a_{jk}-a_{kj}}{2}{\rm d}x_j\wedge{\rm d}x_k. \end{align} Therefore, given a $2$-form $\omega$, we are always able to play the above trick, making the coefficient in front of ${\rm d}x_j\wedge{\rm d}x_k$ asymmetric. In other words, given $$ \omega=\sum_{j,k=1}^Na_{jk}{\rm d}x_j\wedge{\rm d}x_k, $$ we can always write $$ \omega=\sum_{j,k=1}^Nb_{jk}{\rm d}x_j\wedge{\rm d}x_k, $$ where $$ b_{jk}=\frac{a_{jk}-a_{kj}}{2}=-b_{kj}. $$
Now, apply the above result to our target: \begin{align} \omega\wedge\omega&=\left(\sum_{i,j=1}^Na_{ij}{\rm d}x_i\wedge{\rm d}x_j\right)\wedge\left(\sum_{k,l=1}^Na_{kl}{\rm d}x_k\wedge{\rm d}x_l\right)\\ &=\left(\sum_{i,j=1}^Nb_{ij}{\rm d}x_i\wedge{\rm d}x_j\right)\wedge\left(\sum_{k,l=1}^Nb_{kl}{\rm d}x_k\wedge{\rm d}x_l\right)\\ &=\sum_{i,j,k,l=1}^Nb_{ij}b_{kl}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l. \end{align} Play the index-exchanging trick again: \begin{align} \omega\wedge\omega&=\sum_{i,j,k,l=1}^Nb_{ij}b_{kl}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\\ &=\sum_{i,j,k,l=1}^Nb_{li}b_{jk}{\rm d}x_l\wedge{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\\ &=\sum_{i,j,k,l=1}^Nb_{kl}b_{ij}{\rm d}x_k\wedge{\rm d}x_l\wedge{\rm d}x_i\wedge{\rm d}x_j\\ &=\sum_{i,j,k,l=1}^Nb_{jk}b_{li}{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\wedge{\rm d}x_i. \end{align} Now, reorder the indices as $\left(i,j,k,l\right)$ by using the asymmetry property: \begin{align} \omega\wedge\omega&=\sum_{i,j,k,l=1}^Nb_{ij}b_{kl}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\\ &=\sum_{i,j,k,l=1}^N\left(-b_{li}b_{jk}\right){\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\\ &=\sum_{i,j,k,l=1}^Nb_{kl}b_{ij}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\\ &=\sum_{i,j,k,l=1}^N\left(-b_{jk}b_{li}\right){\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l. \end{align} This result eventually yields \begin{align} \omega\wedge\omega&=\sum_{i,j,k,l=1}^N\frac{b_{ij}b_{kl}-b_{li}b_{jk}+b_{kl}b_{ij}-b_{jk}b_{li}}{4}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l\\ &=\sum_{i,j,k,l=1}^N\frac{b_{ij}b_{kl}-b_{li}b_{jk}}{2}{\rm d}x_i\wedge{\rm d}x_j\wedge{\rm d}x_k\wedge{\rm d}x_l. \end{align}
Since $\omega\wedge\omega$ is a $4$-form, in two- and three-dimensional cases, the result must be $0$. From four-dimensions onwards, the result is not necessarily zero, e.g., $$ \omega=\alpha{\rm d}x\wedge{\rm d}y+\beta{\rm d}z\wedge{\rm d}w\Longrightarrow\omega\wedge\omega=2\alpha\beta{\rm d}x\wedge{\rm d}y\wedge{\rm d}z\wedge{\rm d}w. $$