Annie Allerton is Mae’s friend from college. She’s two years older than Annie and isn’t plagued by the same anxieties and insecurities as Mae. Annie is self-assured, social, loving, and generous, and earns Mae’s loyalty after she helps nurse her back to health in college after Mae breaks her jaw. Annie comes from an upper-class family that prides itself on having its ancestry traced back to the Mayflower. She is focused and driven. Annie enters an MBA program at Stanford right out of college and rises to be within the top 40 of the Circle within a few years. On the other hand, she’s also extremely scatterbrained and erratic, which confounds and annoys Mae, as Mae can’t understand how Annie gets everything done. Annie’s cheery, free-loving nature stands in contrast to Mae’s more buttoned-up exterior and weighty self-consciousness.

Annie doesn’t need approval through her job or friendships as much as Mae does, so she is less susceptible to the Circle’s dominating influence. She does, however, suffer some jealousy when Mae rises in the ranks of the Circle. Annie suffers a nervous breakdown after participating in the PastPerfect program, which extensively traces a person’s ancestry. She discovers some ethically problematic information about her family’s past. Annie seriously questions the Circle’s goal of making everything transparent, and whether having some things left as mysteries is better.