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This ensemble comedy project spotlights the life of Charlotte Payne living in New York City looking for love. She enlists the help from Ravi her dating councellor. Charlotte answers some difficult questions revolving around her friends Leslie, Jill, Mike and Wayne while reliving some poignant and humorous moments from her past.100 Questions is produced by Universal Media Studios and Tagline.

Charlotte compete with Wayne on who can have the first one-night stand, while Jill and Leslie help Charlotte land a vegan firefighter. Meanwhile, Mike helps Wayne impress an Israeli model.

Charlotte recalls how she met Wayne; Leslie learns that her ex is remarrying; and Wayne confides that his father has cut him off from his money.

Charlotte dates a man who becomes obsessed with her, going so far as to get a tattoo of her face on his chest, and her friends come up with a lie to help her end the relationship.

Charlotte tries to attract the attention of a guy she's interested in; Mike continues his attempts to scare Leslie; Jill asks Wayne to speak to her class for Career Day.

Mike's extremely friendly new girlfriend makes Charlotte uncomfortable; Leslie becomes enamored with a pair of boots.

Charlotte turns down her boyfriend's proposal; Mike and Wayne compete to see who has the best pick-up line; Jill dates an albino.