All triangles in a triangular strip maintain the same direction / winding order. They do not roll over one after another. Thus, either both triangles will be directed towards you, or far away from you (if your primitive is a flat square shape (that is, convex and does not intersect), where all the vertices belong to the same plane).
PS You know, you CAN make a trianglestrip primitive in an OpenGL application with disabling enabled and see for yourself.
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