Adrian Mole by Sue Townsend

From Wikipedia.com:
The first books concentrate on Adrian's desires and ambitions in life (to marry Pandora Braithwaite, become a published writer of poetry and novels, obtain financial security), and his complete failure to achieve them...the also depict social and political situation in Britain, with particular reference to left-wing politics in the 1980s in the first three books. For example, Adrian's parents divorce at a time when that was comparatively rare in Britain. His mother becomes a staunch feminist and briefly joined the Greenham Common campaigners. Pandora and her parents are part of an intellectualized and left-wing middle-class that attempted to embrace the working class, and which was only just becoming apparent at the time.

The Secret Diary of Adrian Mole, Aged 13¾, The Growing Pains of Adrian Mole, The True Confessions of Adrian Albert Mole, Adrian Mole and the Small Amphibians, Adrian Mole: The Wilderness Years, Adrian Mole: The Cappuccino Years, and Adrian Mole and the Weapons of Mass Destruction.