On his depressing 40th birthday, Charlie meets his alter ego, an pint-sized mouth in a long coat, who helps start to get it together, and helps him to get his promotion.

To celebrate his anniversary right, Charlie takes Hugh's advice and sets up a romantic anniversary celebration; unfortunately it's the same night he must make a business dinner.

Hugh is horrified when Charlie decides it may be time to get a vasectomy.

With Hugh's help, Charlie learns how to deal with his mother-in-law.

A co-worker chases Charlie in search of a fling, which is something Charlie also needs because two months earlier Helen left with the kids.

When a co-worker dies, Charlie travels to Atlantic City to complete the man's dream of taking a $100 dollars and gambling it away.