In a funny, thought-provoking first-person account, a young Christian woman describes the challenges of keeping one’s faith while looking for romance in the big city. Here are some questions for discussion.

1. While Anna “knows in her head” that marriage shouldn’t be the basis of her purpose in life, she can’t seem to find an alternate source of identity. Do you think that it is possible to change this ourselves? Or does the change have to happen to us? What do you tend to most find your identity in (relationships, work, family, etc.)?
2. In the book, Anna admits that she thinks heaven sounds kind of lame. What do you think heaven will be like — is it someplace you would genuinely like to be? What do you think has shaped your ideas of heaven?
3. One thing Anna struggles with throughout the book is a tendency to fragment herself and share only certain parts with other people — which she sees as bad. Do you agree that this is unhealthy? How have you seen this tendency — for good or bad — in your own life or that of friends?
4. Throughout the book, Anna gradually realizes she has had a lot of naive or unrealistic expectations about men, relationships, sex and romance. Have you had that experience? What are some expectations you’ve had to reject or reconsider?
5. In part 1 of the book, Anna talks about both the things she learned from her father and what she wished their relationship had provided. What are the blessings and shortcomings you’ve experienced with your own father?
6. After moving on from her crush on the Married Man, Anna winds up dating a string of unsuitable men. Has there been a time in your life when disappointment or bitterness led you to make some similar choices?
7. On her date with Ad Weasel, Anna suddenly realizes she had a sexual standard she’d not been aware of. Do you agree with what that standard is? Why or why not? How might thinking through her standards beforehand have been a help? How were her early high school standards short-sighted?
8. Etta James taught Anna to associate inner sadness with romantic disappointment or need. What do you usually attribute emotional downturns to? Are there any particular comforts, thoughts or images that you usually turn to in times like that?
9. After her summer project, Anna goes through a serious phase of spiritual questioning. Do you think it’s healthy to do that? Have you ever had a season like that? How did people respond to your questions?
10. Even though Anna experiences disappointment in her involvement with the group College Students, she never stops going to church. How important do think community is in the life of faith? Have you ever had times when a community let you down or played a significant role in your growth as a person?
11. Throughout the book, Anna struggles with trusting that God knows what is best for her sex and romantic life. What is it hardest for you to trust God about?
12. During her spiritual crisis, Anna admits that certain changes in behavior stemmed more from anger toward God than anything else. In times where you felt you were drifting, what was the cause in your changed behavior? Does it make a difference?
13. What would you do if a friend of yours was interested in a married man? How would you council her? What do you think of how Anna handled her crush?
14. In the book, Anna has several different experiences with evangelism (summer project, a trip to India, neighborhood outreach with Poster Boy’s church). What factors seemed to make a difference in whether these experiences were positive or negative?
15. Throughout the book, Anna talks about ways books, music and movies shaped her expectations and ideas about relationships, sex and romance. Do you agree that these things can influence our ideas, even if we aren’t aware of it? What books, movies or songs have had the biggest impact on you? What have they taught you?

Visit Anna Broadway’s blog, the inspiration for Sexless in the City.