Chapter 1: When Waiting Makes You Broken

1. The Bleeding Woman experienced a major—and unwanted—change in her life when she started bleeding. Have you experienced any changes in your life (large or small) that were unwanted or difficult? How have those changes affected the course of your life?

2. Ann’s struggle with trichotillomania forced her to start coming to terms with her own brokenness because she couldn’t do anything to fix it. What are you waiting for God to heal, or fix, or renew in your life?

3. Are there any good sides to brokenness? How might the brokenness you feel be a gateway to knowing God’s love in a new way?

4. Moving forward: Spend some time in prayer, asking God to show you his love through your brokenness.

Chapter 2: When Waiting Makes You Weak

1. Ann shares that with trich, she often felt that she should “try harder” and be able to “get it together.” Have you ever felt weak in the one area you wanted to be strong? What happened?

2. The Bible says that God’s power is made perfect in our weakness (see 2 Corinthians 12:9). What do you think this verse means?

3. Ann writes, “The ways I fail and the ways I don’t measure up actually act as a vehicle to meeting Jesus in my daily life” (page X). In what ways have you seen God work in the weak areas of your life or the lives of those you love?

4. Moving forward: Write down the places in your life that feel weak, and ask Jesus to show you how those places provide an opportunity to meet with him in a deeper way. Take note of how he meets you in the coming days.

Chapter 3: When Waiting Costs You Everything

1. The Bleeding Woman spent all her money seeking healing. Have you ever spent a lot of money, time, or energy trying to fix an area of brokenness in your life? Did it work?

2. Ann shares that hiding trichotillomania from her friends cost her a great deal in terms of time, energy, and friendship. Have you ever tried to hide a weakness from those closest to you? What did it cost you?

3. We can rest in knowing that Jesus has already paid the highest price for our struggles through his death on the cross (see 1 Peter 1:18-21). What would it look like to admit ourinability to be self-sufficient (see page X) and invite the Lord into our weakness and waiting? How might our lives—and our friendships—be transformed?

4. Moving forward: Read 2 Corinthians 3:4-5 out loud, and then thank the Lord that “our sufficiency is from God,” not from ourselves. Pray for the grace to rely on him this week.

Chapter 4: When Waiting Claims Your Identity

1. Ann writes about how she always wanted to be identified as “beautiful.” How do you long to be identified?

2. One of the reasons Ann struggled with her weakness was because “it slithered into [her] identity” (page X). Are there any areas in your life where you identify yourself by your struggle, your sin, or what you lack?

3. In Christ we have a new identity that is determined not by our brokenness or sinfulness but by his love. What practical steps can you take this week to focus your heart and mind on how Christ identifies you?

4. Moving forward: Write out one or two verses that declare your identity in Christ (Ephesians 2:10 and 1 Peter 2:9 are great places to start). Read them every day, reminding yourself of who you truly are.

Chapter 5: When Waiting Feels Offensive

1. When God says no to what we want, it’s easy to take offense. Are there any places in your life where you are feeling offended by God? What prompted those feelings?

2. The Bleeding Woman kept her heart tender toward God because she clung to hope. In what area of your life do you need more hope in God’s love for you?

3. What’s the difference between being honest with God and being offended by him? What can you do to remain tethered to God when you’re on the brink of offense?

4. Moving forward: Make a list of times in your life when you have felt offense toward God, and ask him to forgive you. Tear the paper into pieces and throw the pieces away. Then read Romans 8:28, and ask the Lord to increase your trust in his love for you.

Chapter 6: When Waiting Brings You Shame

1. Ann has struggled with shame over trichotillomania for most of her life. Has the feeling of shame ever played a role in your life? How?

2. The lie of shame is that it pairs our worth with our weakness. In what ways have you believed the lie that your worth is directly connected to your weakness, sin, or struggle?

3. Hebrews 12:2 says, “For the joy set before him [Jesus] endured the cross, scorning its shame, and sat down at the right hand of the throne of God” (NIV). What do you think itmeans that Jesus scorned the shame of the cross? What might it look like to scorn the shame in your own life?

4. Moving forward: Take some time this week to reject the power of shame in your life by accepting the freedom Christ has won for you. Read Romans 8:1; Romans 5:6-11; and 1 John 3:19-20, and thank the Lord for what he has done.

Chapter 7: When Waiting Feels Like Suffering

1. Ann says that the Bleeding Woman’s suffering was significant to Jesus. “He understood that her waiting had been part of her suffering—that the waiting itself had caused her suffering” (page X). Have you ever felt like your pain wasn’t as significant as someone else’s pain? How do you think Jesus would view your suffering?

2. Ann writes, “I didn’t have to worship my pain with hymns and praise to let it be the driving force in my life. I just had to let it uproot God as the central focus” (page X). Has suffering ever become the driving force in your life? What was the result?

3. Ann writes, “Jesus can affirm our suffering because he has suffered it with us” (page X). How does your perspective on your suffering change when you realize that Jesus suffered too?

4. Moving forward: Take some time to pray this week, asking Jesus to reveal his nearness to you in your suffering and to give you new perspective on how he has suffered with you. Read John 19, and thank Jesus for what he has already suffered on your behalf on the cross.

Chapter 8: When Waiting Is Risky

1. The Bleeding Woman took a risk by reaching out as an unclean woman to touch Jesus. Have you ever taken a big risk with something close to your heart? What happened?

2. It feels risky to continue to open our hearts to the Lord when our dreams and desires don’t line up with reality, but it would be far worse to miss the opportunity to grow in closeness and intimacy with God. In what ways are you holding back your heart from the Lord? What risk is he calling you to take?

3. It’s a risk to tell others about our brokenness, because we can’t control how they will respond. But opening up to others actually paves the way for deep connection. Is there someone you need to risk being vulnerable with—someone who needs to hear your heart?

4. Moving forward: Ask God for courage, and then share your story with a trusted friend this week. Ask your friend for encouragement and prayer—and offer the same.

Chapter 9: Waiting with Grace

1. Although most of us are still waiting for something, the grace we receive in our trials is knowing that God is with us in the waiting. Have you ever experienced God’s presence in the midst of struggle and pain?

2. As Christians, we have the grace of the Holy Spirit dwelling inside us forever. How can that truth change our perspective on waiting?

3. Ann says that the healing we long for here and now is “only a shadow of the full healing that will come in the new heaven and the new earth” (page X). How does this broader perspective help us as we face unfulfilled longings and unanswered prayers?

4. Moving forward: Read Revelation 21:1-5, and ask God to fill you with hope for the full healing and wholeness that will come when we reach our heavenly home.

Chapter 10: Hope for the Waiting Ones

1. The book of Hebrews tells us that hope and faith are inextricably intertwined: we can’t have faith without hope (see Hebrews 11:1). If you had to measure the amount of hope you have right now on a scale of 1 to 10, where would your hope fall? Why?

2. Ann writes that when our hope is placed in a person, in an opportunity, or in our own bodies, it will fail. But hope in Jesus and in his coming Kingdom will never disappoint. How can we continue to hope when our circumstances don’t seem to be budging?

3. The Bleeding Woman experienced restoration with her community, to God, and to herself after her encounter with Jesus. Which kind of restoration are you in need of right now?

4. What new insights into the story of the Bleeding Woman have you gleaned from reading this book? What have you learned about what it looks like to wait well?

5. Moving forward: Ask God to restore you in every way you need it. Read 1 Peter 1:3-9, and ask the Lord to give you the “joy that is inexpressible and filled with glory” as you wait for him.