[Elena]
If he feels guilty about asking you for things then he is NOT ready for a relationship. You guys most likely rushed into getting engaged and he's emotionally constipated. I like Damon, I do, but he does not deserve you.
If you get back together with him I will shake you. I seriously think you two do need some time apart and then you can regroup in a few months to go back at things. He needs to see what life is like without you and really appreciate you. I can't believe he would do that and if Stefan did that then there would be divorce papers on the kitchen table immediately.
And you better not stay friends with this person that encouraged this cheating. They are not truly your friend. UGH I WANT TO RIP SOMETHING APART