Firstly, for proper experience, play the games "in order". They are not directly related plotwise, but I don't think the overall experience works quite well if you play A STRANGER COMES CALLING second.

Now, given the title you wouldn't be entirely wrong in believing this to be a one joke experience, as indeed much of the experience boils down to just that: Steve has severe social anxiety and simple situations become needlessly complicated because of this. The first game in particular is a pseudo-RPG in how your objective is to try to find a way to calm Steve down enough for an eventual "stat check". Obviously along the way you enjoy all the ways in which you can fail, but this is how the gameplay loop is justified. There's a minor "wholesome game" undertone to how some of the mini-scenarios are played out, but this one's still at its core a comedy.

Then comes DON'T TURN YOUR BACK ON THE OCEAN, and things change. While there's still some Henry Stickam-esque "see all the funny ways in which you can fail" aspect, this time the plot is actually fully linear and more in line with a visual novel. And then... I won't spoil it (any more than the intrinsic "well, there's a twist" spoiler), but the whole thing becomes more than just a simple silly comedy. I am not sure if this change will be entirely welcome by everyone playing, but in my experience it did manage to elevate the experience.