For the square, pentagon, hexagon, heptagon and octagon, the number of diagonals is $2$, $5$, $9$, $14$, and $20$. Systematic counting reveals the pattern:$$2(n-3)+(n-4)(n-3)/2=\frac{n^2-3n}{2}$$
Diagonals have $\frac{n-3}{2}$ different sizes for odd $n$, and $\frac{n}{2}-1$ for even $n$.
Thus in the regular heptagon diagonals have two different lengths, an equal number of each. Shorter diagonal $AC$ intersects only with the four diagonals drawn from adjacent point $B$. But longer diagonal $AD$ intersects with six: three drawn from $B$ and three from $C$. Of the $7+7=14$ diagonals in the heptagon, depending on whether our randomly chosen first diagonal is short or long, the odds of randomly choosing a second diagonal that intersects it will be either $\frac{4}{13}$ or $\frac{6}{13}$. Since there are an equal number of long and short diagonals, can we take the arithmetic mean and say the odds are $\frac{5}{13}$ in this case?
Continuation, Elaboration & Conclusion
A second random diagonal in an $n$-gon may cross the first, but the $(n-2)th$ diagonal must cross one of the preceding diagonals, whether all radiate from one vertex or proceed across the polygon in stepwise fashion, as may be seen in the example below.
This at least gives a boundary for the number $N$ of diagonals possible before an intersection occurs:$$2\le N\le n-2$$
But this window can be narrowed. As already noted, regular polygons (for $n>5$) have diagonals of different lengths, on which different numbers of crossings may occur. But for odd $n$ there are $n$ diagonals of each different length, so that none is favored in a random selection. For even $n$ there are likewise $n$ diagonals of each length, except for the greatest, the "spokes" of the wheel, which are $\frac{n}{2}$ in number. An array may help here. $$\begin{array}{c|cccccc}n & \text{number of diagonals} & d_1 & d_2 & d_3 & d_4 & d_5\\\hline4 & 2 & 2\\5 & 5 & 5\\6 & 9 & 6 & 3\\7 & 14 & 7 & 7\\8 & 20 & 8 & 8 & 4\\9 & 27 & 9 & 9 & 9\\10 & 35 & 10 & 10 & 10 & 5\\11 & 44 & 11 & 11 & 11 & 11\\12 & 54 & 12 & 12 & 12 & 12 & 6\\13 & 65 & 13 & 13 & 13 & 13 & 13\end{array}$$Guaging the probability of a second diagonal crossing a first requires taking into account the number of possible crossings for each $d_k$ in the $n$-gon. The next array shows the number of crossings possible on the various diagonals.$$\begin{array}{c|ccccc}n & \text{crossings for:} & d_1 & d_2 & d_3 & d_4 & d_5\\\hline4 & & 1\\5 & & 2\\6 & & 3 & 4\\7 & & 4 & 6\\8 & & 5 & 8 & 9\\9 & & 6 & 10 & 12\\10 & & 7 & 12 & 15 & 16\\11 & & 8 & 14 & 18 & 20\\12 & & 9 & 16 & 21 & 24 & 25\\13 & & 10 & 18 & 24 & 28 & 30\end{array}$$If the number of crossings$$d_1=n-3$$$$d_2=2n-8$$$$d_3=3n-15$$$$d_4=4n-24$$$$d_5=5n-35$$then generally the number of crossings for$$d_k=kn-k^2-2k$$If he probability of any one of the $k$ different diagonals crossing another is the number of possible intersections on that diagonal divided by the remaining $n-1$ diagonals, and the probability of a random second diagonal crossing the first is the arithmetic mean of those $k$ different probabilities, then e.g.for $n=13$ we have$$\frac{10+18+24+28+30}{5\cdot 64}=\frac{22}{64}=.344$$Using the rules derived above we can accordingly compute probabilities for larger $n$. E.g. there are $\frac{n^2-3n}{2}=1034$ diagonals in the $47$-gon, in which there are $22$ different groups of $47$ diagonals each. Summing the twenty-two numerators we get$$\frac{7590}{22\cdot 1033}=\frac{345}{1033}=.334$$This confirms——and is confirmed by——the more elegant argument in the comment of @Misha Lavrov, that the probability should converge to $\frac{1}{3}$ as $n$ increases. If this line of argument is sound, it seems three diagonals should yield an interior crossing.
Addendum: Expressed generally as a function of $n$, I find the numerator, e.g. for $n=13$, $10+18+24+28+30=110$ to be$$\frac{n^3-6n^2+11n-6}{12}$$and the denominator $$\frac{n-3}{2}\cdot \frac{n^2-3n-2}{2}=\frac{n^3-6n^2+7n+6}{4}$$Thus, inverting the denominator and multiplying, the ratio is$$\frac{n^3-6n^2+11n-6}{12}\cdot \frac{4}{n^3-6n^2+7n+6}$$ which gets increasingly close to $\frac{4}{12}= \frac{1}{3}$ with increasing $n$, for example $.3334796$ for $n=97$, $.3333675$ for $n=199$, and $.3333347$ for $n=997$.