To me it was one of those things where it makes sense in the reality of the movie. Like the Callahan auto parts factory being the major employer and financial source in Sandusky, it's something that furthers what is happening. They validate the choice by having the poolside exchange where Big and Little Tom remark on her attractiveness, so it doesn't seem odd that an attractive young man like the Rob Lowe character.
Think of it like Lois from Family Guy--to me, she doesn't appear attractive, but in the world of the show, she's a 10, an idea that's reinforced through the direct comments of the other characters.
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