When Kaling was a child, her parents dressed her brother and her like Bert and Ernie. When she began working in television, she was excited about the prospect of having stylists and enjoying fashion. However, when she began showing up for photo shoots, many of the stylists did not know what to do with a larger body than the Hollywood standard of size zero. Kaling lists the types of outfits stylists tried to make her wear: Dark colors to hide her features; cap sleeves to conceal her upper arms; or baggy clothes like poet blouses, shawls, or muumuus.

In 2011, Kaling was named one of People magazine’s Most Beautiful English-Speaking Persons in North America. She was looking forward to showing up for the shoot and being presented with designer dresses, but the stylist only brought gowns in sample sizes. The only dress that fit was a formless navy shift. Kaling went to the bathroom and cried, but a note on the wall scribbled by a middle school student made her laugh.

She left the bathroom and picked out a beautiful gown from one of the racks. Kaling told the stylist that this was the dress she wanted to wear, and the stylist explained that it would not fit her.