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I think that guys should always pay for the first date. I'm usually conscious of what I order though. I try to stick to something moderately priced (i.e. not a $10 nacho plate, but not a $40 steak entree). I also don't really drink alcohol, so I never order any on dates anyway.
As far as this guy is concerned, he can't really be mad at her for ordering it. You need to be conscious of where you're taking her. Don't try to impress a girl by taking her to nice place with wine that will destroy your bank account if she orders it. Keep it real and take her to Maccaroni Grill, TGI Fridays, or some other chain. I'm sure if a girl likes you enough, it won't matter.
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