I have done this problem over and over again. I even looked up tutorials on how to properly use law of sines. It's rather embarrassing that I'm struggling so much wish this simple trigonometric stuff.
Here's the picture of the triangle. I'm trying to solve for angle $\angle{C}$. Angle $\angle{C}$ is definitely supposed to be obtuse.

I keep getting: $$\dfrac{\sin(21.55)}{7.7} = \dfrac{\sin(C)}{16}$$
I simplify and take the $\arcsin\left(16 \cdot \dfrac{\sin(21.55)}{7.7}\right)$
And I can't get an obtuse angle. Anyone know why?
Typically, the range of $\arcsin(x)$ is $[-\pi/2,\pi/2]$. This thereby eliminates the obtuse angle you want. To get the obtuse angle you want, all you need to do is to realize that $$\sin(\pi - \alpha) = \sin(\alpha)$$ Hence, $180^{\circ}- \arcsin(16 \sin(21.55^\circ)/7.7)$ should give you the answer you need.