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Only, Jen had so much more of Drue than Anna ever could. And the eventually let his guard down a little with Anna and was sweet to her. Again, the same could have happened with Jen. It would have taken a lot more work, because Jen obviously wasn't just some girl Drue had sex with but I think that would have been the best part. The building stages of their relationship.
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ITA. Would've been amazing to see that build up. She would make him work his ass off for it.