A série mostra Whitney Cummings, interpretando uma versão fictícia de si mesma, e seu namorado com quem ela mora. Mesmo os dois tendo decidido não se casarem, Whitney faz questão de mostrar o quanto são comprometidos em seu relacionamento de 3 anos, mas ela começa a temer que o relacionamento esteja caindo no tédio e preocupa-se que a relação possa acabar. Por causa do que ela vê e ouve ao seu redor, envolvendo outros relacionamentos, ela decide usar métodos não convencionais para manter o romantismo com a ajuda de seus melhores amigos.

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1x01 - Pilot
1x02 - First Date
1x03 - Silent Treatment
1x04 - A Decent Proposal
1x05 - The Wire
1x06 - Two Broke-Up Guys
1x07 - Getting To Know You
1x08 - Clarence!
1x09 - Up All Night
1x10 - Christmas Is Cummings
1x11 - Private Parts
1x12 - Faking It
1x13 - Codependence Day
1x14 - Mind Games
1x15 - Lance!
1x16 - 48 Hours
1x17 - Mad Women
1x18 - Homeland Security
1x19 - The Ex Box
1x20 - G-Word