diff --git a/pkg/cli/cmd.go b/pkg/cli/cmd.go
index 8b44358..7be5e4b 100644
--- a/pkg/cli/cmd.go
+++ b/pkg/cli/cmd.go
@@ -239,6 +239,15 @@ var newCmd = &cobra.Command{
 		}
 
 		fmt.Println()
+
+		err = conversation.GenerateTitle()
+		if err != nil {
+			Warn("Could not generate title for conversation: %v\n", err)
+		}
+		err = store.SaveConversation(&conversation)
+		if err != nil {
+			Warn("Could not save conversation after generating title: %v\n", err)
+		}
 	},
 }
 
diff --git a/pkg/cli/conversation.go b/pkg/cli/conversation.go
index 7a3d1d0..2cdfa8a 100644
--- a/pkg/cli/conversation.go
+++ b/pkg/cli/conversation.go
@@ -1,5 +1,10 @@
 package cli
 
+import (
+	"fmt"
+	"strings"
+)
+
 // FriendlyRole returns a human friendly signifier for the message's role.
 func (m *Message) FriendlyRole() string {
 	var friendlyRole string
@@ -15,3 +20,37 @@ func (m *Message) FriendlyRole() string {
 	}
 	return friendlyRole
 }
+
+func (c *Conversation) GenerateTitle() error {
+	const header = "Generate a short title for the conversation below."
+	prompt := fmt.Sprintf("%s\n\n---\n\n%s", header, c.FormatForExternalPrompting())
+
+	messages := []Message{
+		{
+			Role:            "user",
+			OriginalContent: prompt,
+		},
+	}
+
+	model := "gpt-3.5-turbo" // use cheap model to generate title
+	response, err := CreateChatCompletion(model, messages, 10)
+	if err != nil {
+		return err
+	}
+
+	c.Title = response
+	return nil
+}
+
+func (c *Conversation) FormatForExternalPrompting() string {
+	sb := strings.Builder{}
+	messages, err := store.Messages(c)
+	if err != nil {
+		Fatal("Could not retrieve messages for conversation %v", c)
+	}
+	for _, message := range messages {
+		sb.WriteString(fmt.Sprintf("<%s>\n", message.FriendlyRole()))
+		sb.WriteString(fmt.Sprintf("\"\"\"\n%s\n\"\"\"\n\n", message.OriginalContent))
+	}
+	return sb.String()
+}