Does anyone see the similarities in the Leonard character and the Neil Klugman character in Goodbye Columbus? Both characters are average looking, jewish, middle class single guys in there twenties. There both dating beautiful upper class women that come from high society. I love both films, but the reality for me is that this could only happen in the context of a fictional film. I think that HBK took the snob factor out of the equation, because in reality both these guys wouldn't get the time of day from these two women. Leonard in The Heartbreak Kid would have zero chance in closing a beautiful rich wasp social light. The fact that he's jewish would kill his chances right from the start. Goodbye Columbus is the same story, even though the characters are both jewish, the jewish woman would never give a lower class jewish guy the time of day, and you may ask how can I be so sure of my theories? I've seen it first hand lol and lived it.
Richard Benjamin's character in Goodbye Columbus is generally much more appealing and sympathetic than Leonard. He seemed like an intelligent, mature, 'together' guy, with a heart of gold, and it's not terribly difficult to see why a woman, upper class or not, Jewish or not, would be attracted to him.
Leonard Cantrow as played by Charles Grodin on the other hand is vastly less likable and relatable to the viewer. He's actually not a bad looking guy at all - he's tall, fit, well-dressed, and has great hair - but the way he speaks and comes across is totally bizarre and offputting. It's like he's a wiseass without being at all intelligent. Indeed, while Jewish characters are usually stereotyped as being smart, even if it's a nebbishy or sleazy kind of smart, Leonard actually comes across as inarticulate and simple-minded. He actually kind of reminded me of Rocky Balboa. He talked as if he had been slugged in the head one too many times. Was Charles Grodin drunk during the filming of 'Heartbreak Kid'? There are numerous times when he sounds/acts like it.
There are also quite a few moments when he seems like a psychopathic lunatic and his 'determination' seems more like insane obsession. And not even the stock-movie-character insane, I mean actual real-life single-minded unhealthy obsessiveness insane, which I guess is a testament to Grodin's acting ability.
The one thing he does have going for him is mad confidence, which is typical of psychopaths. It's not implausible that he could get a woman like Kelly to *beep* him, but her wanting to marry him, especially against the wishes of her father, is very unrealistic.
I do agree with you that Leonard being able to upgrade to a girl like Kelly and then marrying her against the wishes of her elitist wasp father can only work in the context of a Neil Simon written comedy, in reality he doesn't even get to first base. On Leonard being a psychopath, I have to strongly disagree with you on that, just because he went after Kelly it doesn't make him a psychopath, so he has what you call "mad confidence," does that ego/confidence mean he is now labeled a psychopath?