Sporting goods salesman Lenny Cantrow (Charles Grodin) is engaged to Lila (Jeannie Berlin), but frustrated by her belief in no sex before marriage. The big day arrives, and after the ceremony they pack their bags and head off on a cross-country drive from New York to Miami and the Florida resort they have prepared for the honeymoon. However, on the way Lila has a habit of mentioning that they will spend forty to fifty years together, which begins to prompt Lenny to have second thoughts, especially considering that his new spouse has revealed a preference for messy egg salad sandwiches, insists on out of tune singing and to top it all that long-awaited sex wasn't all he hoped for, either. So it turns out that the honeymoon will be the worst thing possible for the marriage...
Probably one of the most excruciating comedies ever to come out of Hollywood, The Heartbreak Kid was scripted by Neil Simon from a short story by Bruce Jay Friedman. Some scenes, many scenes actually, leave you squirming with embarrassment as our anti-hero throws away the life to which he was best suited to doggedly pursue the woman of his dreams - Lila, the previous woman of his dreams he steadily forces out of his existence. Some prefer Midnight Run, but this is surely Grodin's best performance as he spins outrageous lies, insinuates his way into people's lives, and generally acts like a self-deluding heel.
It's Lenny's capacity for self-delusion that keeps the plot bubbling away after he has a chance encounter with rich blonde college student Kelly (Cybill Shepherd) on the beach. She's toying with him when she walks up and tells him he's lying in her spot, but for Lenny it's love at first sight. Those feelings he had for Lila all of two days before - before they were married, that is - are effortlessly transferred to Kelly and when Lila foolishly stays out in the sun too long without tanning lotion on, she has to stay in their hotel room for a day. This gives Lenny a perfect opportunity to get to know Kelly better.
You can tell that Kelly is flattered by Lenny's devotion, but can't shake the feeling that she's playing him for a fool, which isn't difficult, because the man is a fool. Kelly's millionaire banker father (Eddie Albert, on as excellent form as the rest of the cast), however, sees right through him, and is determined he doesn't get any closer to his daughter. And so Lenny's excuses to Lila mount up as he tells her, for example, he was in a car crash with an old army buddy when he was really inviting himself to dinner with Kelly's family, and there comes a point when he decides there's only one thing for it: a divorce after less than a week so he can be free to marry Kelly, whether she wants to or not.
From this results the film's most famous sequence, a masterclass of cringeworthy humour as Lenny finally takes Lila out for dinner to a seafood restaurant to break the bad news, just as she's starting to enjoy herself as well. Although we can see they are a good match, Lenny can't allow real life to get in the way of his romantic ideals, and his methods of letting Lila down gently are as pathetic as expected, leaving her a quivering wreck in front of the other customers. The Heartbreak Kid leaves you dreading scene after scene, just because you can see that Lenny's not going to get any better - the last act features him chasing Kelly back to her home in Minnesota and in a no-less-uncomfortable development, winning her over. Peerless performances throughout, despite leaving you with constantly conflicting sympathies, ensure that the comedy remains compelling in a "watch through your fingers" kind of way, yet mostly it makes you wince. Music by Garry Sherman.