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while not about a girlfriend, i used to do something similar. when i moved into my frat house, we started playing poker. because i was one of two that had any real experiance, when we'd go over rules or conflicts, i'd often relate what had just happened at the table to when i had played with my old poker group. when it came to poker, everything i knew was related to that group and so i would use them as examples and stories. i may just be that he's relating things to what he knew, although if he would really say that about disney land, it could be more.
just a thought.
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