The film starts with Larry Hubbard (Martin) having a very bad day. He breaks up with his girlfriend after finding her in bed with another man, and she kicks him out of the apartment. Upset and confused, he bumps into a pathetic-looking guy named Warren (Charles Grodin), who asks if he is a "first-time lonely guy".
And thus Larry is introduced to the world of "lonely guys", a subculture of men who share tips and coping strategies for surviving the single life. With Warren's advice and friendship, Larry begins to reassemble his life, navigate the completely absurd situations he frequently encounters (or creates), and even pursue a new love interest: the beautiful, cheerful, and six-times-divorced Iris (Judith Ivey).
This film provides examples of:
- Black Comedy: Aside from the Suicide as Comedy listed below, we have Larry's vision of his possible future lonely death. His unmourned corpse is stuffed into a trash can on the sidewalk and then thrown into the back of a garbage truck.
- Butt-Monkey: Warren.
- The Cameo:
- Cardboard Pal: Warren fills his apartment with black-and-white celebrity cut-outs to stave off loneliness. Larry follows suit, and a lonely cop asks where he can get some.
- Exploding Calendar: Subverted. When Larry begins writing A Guide for the Lonely Guy, the pages begin to fly off his calendar...because he left the window open, and the wind is blowing.
- The First Cut Is the Deepest: Iris has been married six times. She genuinely feels a strong attraction to Larry, but she is so terrified of getting hurt again that she can't commit to an actual relationship.
- I Should Write a Book About This: Larry decides to give up on his romance novel and write A Guide for the Lonely Guy instead. Oddly, this is well before the end of the movie.
- Lonely Bachelor Pad: Larry's new place is definitely this at first. Then Warren offers some tips on making it less lonely (which boils down to adding lot of ferns and cardboard cutouts of celebrities). It's debatable whether it works or not.
- Mills and Boon Prose: Larry's attempt to write a romance novel.Larry: [reading aloud] "Soon the primal fire began to burn in Lady Hookstraten's body. Her hips twitched and trembled as each fireball from Oliver's powerful cannon erupted like molten lava into the quivering mouth of her ever-fluttering love purse."
- Mistaken from Behind: When Larry bursts into what he thinks is Iris's wedding and begs for her to reconsider (see Speak Now or Forever Hold Your Peace, below), he and the audience don't see that the bride isn't Iris until she turns around.
- Motor Mouth: Larry's rental agent says everything very rapidly.
- Really Gets Around: Danielle. Within 15 minutes of kicking Larry out of the apartment, she leaves the original guy she was cheating on him with for an entire rock band.
- Seinfeldian Conversation: Larry and Warren have a few. One is about hair; Warren starts off by asking why people with more hair than him don't get charged more for haircutsnote , and then the conversation drifts a bit...Larry: You know, the guys who always keep their hair are the guys who have no use for it at all, they're not trying to impress anybody.Warren: Who's that?Larry: Like bums. You ever seen a bald bum? They always have a beautiful head of hair.
- Shout-Out: Larry shows up to a costume party dressed as Charlie Chaplin's Tramp.
- Speak Now or Forever Hold Your Peace: Larry bursts into Iris's wedding to tell her that she shouldn't be marrying the guy. He got the wrong church, though the bride takes his advice anyway.
- Suicide as Comedy: Warren is about to jump off a bridge, and Larry has to talk him down. And he is absolutely terrible at it. (When asked to name one thing Warren has to live for, the best he can come up with is "Not dying".) Meanwhile, other suicidal people are jumping off and plopping into the water at a truly ridiculous rate.Suicidal guy: Excuse me. Are you using this railing?Warren: No.Suicidal guy: Thank you.Warren: You're welcome.[Guy jumps off the railing screaming]
- Twin Threesome Fantasy: After his book takes off and he becomes famous, we see Larry in bed with "the Schneider twins"...and Dr. Joyce Brothers for good measure.
- Unsettling Gender Reveal: When Larry tries to ask his rental agent out, the reply he gets is "I'm a man." It's unclear if this is the truth, or just a lie to stop him from ever asking again. note