Looks kind of wet... Was it just watered?

Yes, it was. It has blossoms and looks like it is starting to bloom but the roots in the ground concern me.

Are those two different plants in the two pics? The second one looks healthier. I honesty thought that on the first pic, you started growing your second crop (wilted plant) and you were taking down your first crop (surrounding plant) by pruning it.

I'm not an expert but the grass may be competing with the squash. If it were me, I'd weed out any grass in close vicinity to the squash. Then I'd add mulch. My experience with squash/pumpkins is that they don't like sitting in muddy soil BUT as they grow larger their water requirement grows larger to where you are watering them a lot. So start with a little and increase accordingly as the plant grows.

Do you still have the seed package? If so read the back for planted instructions it may give you a clue. If you bought it in a 3"x3" then it came without instructions.Vining Squash like to be planted on a mound. Watering and soaking the ground around the mound to where the mound takes up water and the leaves stay dry. (little late now sorry)
1-Get rid of the grass around the plant as mav said
2 -dig a moat/trench 3"or more deep around the plant about 10"/12" away from the base of the plant(don't get to close to roots)
3- water only in the trench -letting the water soak over to the roots.
4-mulch under plant to keep stems/leaves dry(if its not to hot were you are gravel will also work)
5- keep those leaves dry or you will have fungus.
If you do this it can make it.