We know that the orbits of Pluto and Neptune overlap. This means that pluto sometimes crosses the orbit of Neptune; will Pluto hit Neptune in any circumstance?
No, Pluto is a so called resonant trans-neptunian object; the orbital period of Pluto is almost exactly 3:2 (1.5) times that of Neptune. This means that every time Pluto nears perihelion and is therefore closest to the Sun and also closest to the orbit of Neptune, Neptune is always at a specific angle (50° according to Wikipedia) in front or behind Pluto. (See for instance Figure 3 and surrounding text in Jewitt, D., Morbidelli, A., & Rauer, H. (2007). Trans-Neptunian Objects and Comets. Springer.)
No. From 1979 to 1999, Pluto was the eighth planet from the sun. In 1999, it slipped beyond Neptune to become the ninth. But Pluto's 248-year orbit around the sun takes it 17 degrees above and below the plane in which Neptune and the other planets travel.
So their paths don't actually cross as they swap positions. Imagine you are the sun in the middle of your back yard. The fence is Neptune's orbit. You toss a boomerang way out over the neighbor's houses and it comes back, being on both sides of your fence during its travels without hitting the fence. Of course, activity like that can be frowned upon, and in Pluto's case helped lead to its demotion.
Reference: Will Pluto Neptune Hit