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I just went through this little fight a few days ago but didn't experience any difficulties. You don't have to leave and come back after talking to his girlfriend though. When you talk to her, one of the dialog options is something like 'I can't wait that long'. If you choose this option, she replies...'oh wait, here he is now', and the guy appears. You may want to try this dialog path if you haven't yet.
-sb
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