Margaret dates Jerry, but she previously went out with Newman.
When Jerry learns that his girlfriend formerly dated Newman, and that it was Newman who ended the relationship, he is quite intrigued. Jerry cannot comprehend why Newman dumped someone so clearly «out of his league» and «wasn't [his] type», so he attempts to find the fault in his girlfriend.
Elaine suggests that there's more to Newman than meets the eye. Jerry says there's less and that he looked into Newman eyes to discover that «he's pure evil».
Margaret becomes suspicious of his scrutiny and challenges him to kiss her. Jerry is unable to overcome his Newman-fueled misgivings enough to do so, and she dumps him.
* Groundhog Day
* Frasier
* Sleeping with the Enemy