Ted - Mary is his wife in real life as well. On the show they split up and he dated Cheryl who is almost 20 years younger and smoking hot.
Larry - The only one that fits the "average to ugly" range is tracy ullman and he is only dating her to get her to reverse the fence law
Jeff - Rich but not famous. He's married to Susie but they got married young and it seems he would divorce her but doesn't want to give her half his stuff so he cheats instead. The women he hooks are sometimes in the the "average to ugly" range for sure.
Then there's Richard Lewis who constantly dates women way younger and way out of his league
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