If you've ever found yourself in the same position you were in last year, or the year before, or the year before that, it's time we've introduced you to the concept of repetition compulsion. Freud's coked out ass may have gotten this right as it's something many of us experience.
The same type of relationship. The same kind of idea. The same kind of work procastination. The same bad experience.
There's a comfort in familiarity whether the familiar experience is harmful or not. Freud was confused by this, particularly the repetition of negative experiences because he believed that we very much moved towards pleasure, which this theory goes against. In one of his patient's therapy sessions he noted, ". . . is obliged to repeat the repressed material as a contemporary experience instead of...remembering it as something belonging to the past." We may have issues letting something sit in the past and moving away from it. We may be obsessed with the feeling it provides for us. There is a repressed instinctual process that moves to cleverly bring about situations (like oh I'm out of money again, or damn that paper is due in 5 hours) that make you think why do I always do this. Your unconscious is a smart, slick bastard that's why. Luckily, the part that knows better, Freud's Ego, can be used to catch yourself beforehand.
I think, however, that we are simply obsessed with Feeling. If we're going to keep repeating experiences, make sure you're creating the kinds of experiences worth repetition.
Freud, five years later: "There is no need to be discouraged by these emendations...so long as they enrich."