I completely agree with ShroudOfFrost (who, by the looks of it, is a fellow HitRecord-er! "Again by heart", dear friend!)...
I was absolutely disgusted by Reed's action, and I saw it coming a mile away by how absolutely infatuated he was by Jill. But, immediately, we went to Kate's to admit what had just happened, but, of course, what are you going to do in a situation like that. It's hard to accept someone's apology immediately after they admit to being unfaithful.
Nevertheless, the story clearly shows that Reed's actions were looked down upon by his whole town, and he even nearly destroys both of his relationships (with Kate and with Jill).
Reed is at that point in his life where he is really trying to figure out who he is as a person. For the past few years, he has felt as though he was pressured into following in his dad's footsteps (although he never actually was, he just felt that obligation and guilt), and he never really got the chance (while coming out of high school) to take some time to figure out where he wanted to go and what he wanted to become.
Then there was also the heavy load involving Kate. Both of Reed's parents, as well as Kate's mother, got killed in that car accident. A tragic even like that is often going to bring two people together. Both Reed and Kate really had nobody else but each other to lean on, and so they felt nearly obligated to date and get engaged. However, although Reed surely LOVES Kate, he was never actually IN LOVE with her like he probably thought that he was. He just needed someone to be there for him, and she needed someone to be there for her as well. They loved each other platonically, and they really are the best of friends -- which makes it all the more wonderful that, in the end, after they've had some time apart and some time to grow up and find their own individual selves without the other person, they were able to remain very close, supportive friends.
As for Jill, Reed was obviously always in love with Jill. I don't really like her character much simply because I dislike ambivalent people with little motivation to take their lives anywhere, but all of the characters are still quite young in the movie. They're all just.. looking for themselves.
And you can't entirely blame a guy who is just trying to look for himself. Maybe you don't get back in a relationship with a person like that, but you can certainly eventually forgive them if they are sincere in their apology -- which Reed certainly is.
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