To solve this problem, we need to find the midpoint of a line segment with the given endpoints.

The formula for the midpoint $M$ of a line segment with endpoints $(x_1, y_1)$ and $(x_2, y_2)$ is:

$M = \left( \frac{x_1 + x_2}{2}, \frac{y_1 + y_2}{2} \right)$

The two endpoints given in the problem are:

$(-8, -9) \quad \text{and} \quad (-5, -3)$

Now, applying the midpoint formula:

$M_x = \frac{-8 + (-5)}{2} = \frac{-8 - 5}{2} = \frac{-13}{2} = -6.5$

$M_y = \frac{-9 + (-3)}{2} = \frac{-9 - 3}{2} = \frac{-12}{2} = -6$

So, the midpoint is:

$M = \left( -6.5, -6 \right)$

Would you like more details on the steps, or do you have any questions about the process?

Here are five related questions to deepen your understanding:

1. How would the midpoint formula change if we were working in three dimensions?
2. What is the significance of the midpoint geometrically in real-life problems?
3. How can you verify that the midpoint divides the segment into two equal parts?
4. What happens to the midpoint if both endpoints are on the same vertical line?
5. How can the midpoint formula be applied in vector geometry?

Tip: Always double-check the signs when performing midpoint calculations to avoid common mistakes with negative numbers.