I think the problem is with the Jeremy character more than with the actor. I don't think he's ever presented as an adequate alternative to Steve Martin's character. We're supposed to think she wants him because he's genuine, but he's too much of a goof.
Considering that Steve Martin wrote this, maybe he is subconsciously trying to present his "rival" in the story as not being so desirable. Maybe he is wanting people to watch the movie and think wow, I wish Claire and Steve had gotten together.
Why pursue her if he's not interested? That she'd respond to him, at all, is a miracle. He's an idiot. Steve Martin is a genius.
The Ray Porter character was rich, successful, and smooth (that bit with the gloves to introduce himself). I don't think it's a miracle at all that she would respond to him. That gold digger chick wanted him and had never even met him.
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