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Milt Erlandsen is trying to turn his life around at age 30. At work, he puts himself forward for more responsibilities. At home, his dating life goes nowhere while the ex-girlfriend of his missing roommate makes a surprising offer. Milt also gets involved in his landlord's seemingly hopeless candidacy for a seat on the city council. Milt tries his hand at media manipulation with more success than he bargained for, leading to the discovery of a dark secret in the past of the girl he loves. When things start to unravel, Milt's charismatic kid sister is there to help.

As the 20th Century draws to a close, liberal syndicated columnist Melanie Dvorak has excellent health, more money than she knows what do with, and a supportive if eccentric husband. Yet she is troubled by anxiety and worries that she is out of touch with her readership. A violent encounter at a fancy boutique in Boston's Back Bay gives her notoriety but not fame on her own terms. As her husband Simon Herbst dabbles in independent film production, Melanie explores unexpected avenues to bring her through the tumult of a new age.

Frieda Hamel loves men. But when it comes to having relationships with them, something always goes wrong. Beginning in college, where Frieda sheds her past as an unpopular, ugly-duckling high schooler, and on into her thirties as a busy career woman, she either dates men who won't commit to her or who ask too much when they do want to get serious. When Frieda meets an exciting younger man, it could be that the things they have in common are their worst habits. Given the chance to transcend her own misanthropy to do the right thing at her workplace, Frieda's professional reputation and...