diff --git a/pkg/tui/conversations.go b/pkg/tui/conversations.go
index 2df825f..6854c52 100644
--- a/pkg/tui/conversations.go
+++ b/pkg/tui/conversations.go
@@ -13,18 +13,22 @@ import (
 	"github.com/charmbracelet/lipgloss"
 )
 
+type loadedConversation struct {
+	conv      models.Conversation
+	lastReply models.Message
+}
+
 type (
-	// send when conversation list is loaded
-	msgConversationsLoaded []models.Conversation
+	// sent when conversation list is loaded
+	msgConversationsLoaded ([]loadedConversation)
+	// sent when each coversation's 'last reply' is loaded
 )
 
 type conversationsModel struct {
 	basemodel
 
-	conversations []models.Conversation
-	lastReplies   []models.Message
-
-	content viewport.Model
+	conversations []loadedConversation
+	content       viewport.Model
 }
 
 func newConversationsModel(tui *model) conversationsModel {
@@ -102,24 +106,29 @@ func (m conversationsModel) Update(msg tea.Msg) (conversationsModel, tea.Cmd) {
 
 func (m *conversationsModel) loadConversations() tea.Cmd {
 	return func() tea.Msg {
-		c, err := m.ctx.Store.Conversations()
+		conversations, err := m.ctx.Store.Conversations()
 		if err != nil {
 			return msgError(fmt.Errorf("Could not load conversations: %v", err))
 		}
-		return msgConversationsLoaded(c)
+
+		loaded := make([]loadedConversation, len(conversations))
+		for i, c := range conversations {
+			lastMessage, err := m.ctx.Store.LastMessage(&c)
+			if err != nil {
+				return msgError(err)
+			}
+			loaded[i].conv = c
+			loaded[i].lastReply = *lastMessage
+		}
+
+		slices.SortFunc(loaded, func(a, b loadedConversation) int {
+			return b.lastReply.CreatedAt.Compare(a.lastReply.CreatedAt)
+		})
+
+		return msgConversationsLoaded(loaded)
 	}
 }
 
-//func (m *conversationsModel) loadConversationLastestReplies(conversations []models.Conversation) tea.Cmd {
-//	return func() tea.Msg {
-//		//lastMessage, err := m.ctx.Store.LastMessage(&conversation)
-//		return nil
-//	}
-//}
-
-//func (m *conversationsModel) setConversations(conversations []models.Conversation) {
-//}
-
 func (m *conversationsModel) headerView() string {
 	titleStyle := lipgloss.NewStyle().Bold(true)
 	header := titleStyle.Render("Conversations")
@@ -127,13 +136,12 @@ func (m *conversationsModel) headerView() string {
 }
 
 func (m *conversationsModel) renderConversationList() string {
-	sb := &strings.Builder{}
-	type AgeGroup struct {
+	type timeCategory struct {
 		name   string
 		cutoff time.Duration
 	}
 
-	type ConversationLine struct {
+	type listItem struct {
 		id           uint
 		short        string
 		title        string
@@ -142,11 +150,10 @@ func (m *conversationsModel) renderConversationList() string {
 	}
 
 	now := time.Now()
-
 	midnight := time.Date(now.Year(), now.Month(), now.Day(), 0, 0, 0, 0, now.Location())
 	monthStart := time.Date(now.Year(), now.Month(), 1, 0, 0, 0, 0, now.Location())
 	dayOfWeek := int(now.Weekday())
-	categories := []AgeGroup{
+	categories := []timeCategory{
 		{"Today", now.Sub(midnight)},
 		{"Yesterday", now.Sub(midnight.AddDate(0, 0, -1))},
 		{"This week", now.Sub(midnight.AddDate(0, 0, -dayOfWeek))},
@@ -160,32 +167,6 @@ func (m *conversationsModel) renderConversationList() string {
 		{"6 Months ago", now.Sub(monthStart.AddDate(0, -6, 0))},
 		{"Older", now.Sub(time.Time{})},
 	}
-	categorized := map[string][]ConversationLine{}
-
-	for _, conversation := range m.conversations {
-		lastMessage, err := m.ctx.Store.LastMessage(&conversation)
-		if lastMessage == nil || err != nil {
-			continue
-		}
-		messageAge := now.Sub(lastMessage.CreatedAt)
-		var category string
-		for _, c := range categories {
-			if messageAge < c.cutoff {
-				category = c.name
-				break
-			}
-		}
-
-		categorized[category] = append(
-			categorized[category],
-			ConversationLine{
-				id:           conversation.ID,
-				title:        conversation.Title,
-				short:        conversation.ShortName.String,
-				lastReplyAge: messageAge,
-			},
-		)
-	}
 
 	// TODO: pick nice color
 	categoryStyle := lipgloss.NewStyle().
@@ -198,35 +179,39 @@ func (m *conversationsModel) renderConversationList() string {
 		MarginBottom(1).
 		PaddingLeft(2)
 
-	for _, category := range categories {
-		conversationLines, ok := categorized[category.name]
-		if !ok {
-			continue
-		}
+	ageStyle := lipgloss.NewStyle().Faint(true)
+	titleStyle := lipgloss.NewStyle().Bold(true)
+	untitledStyle := titleStyle.Copy().Italic(true).Faint(true).SetString("(untitled)")
 
-		slices.SortFunc(conversationLines, func(a, b ConversationLine) int {
-			return int(a.lastReplyAge - b.lastReplyAge)
-		})
+	var currentCategory string
+	sb := &strings.Builder{}
+	for _, c := range m.conversations {
+		lastReplyAge := now.Sub(c.lastReply.CreatedAt)
 
-		ageStyle := lipgloss.NewStyle().Faint(true)
-		titleStyle := lipgloss.NewStyle().Bold(true)
-		untitledStyle := titleStyle.Copy().Italic(true).SetString("(untitled)")
-
-		fmt.Fprintf(sb, "%s\n", categoryStyle.Render(category.name))
-		for _, c := range conversationLines {
-			tstyle := titleStyle
-			if c.title == "" {
-				tstyle = untitledStyle
+		var category string
+		for _, g := range categories {
+			if lastReplyAge < g.cutoff {
+				category = g.name
+				break
 			}
-			heading := fmt.Sprintf(
-				"%s\n%s",
-				tstyle.Render(c.title),
-				ageStyle.Render(util.HumanTimeElapsedSince(c.lastReplyAge)),
-			)
-			sb.WriteString(conversationHeadingStyle.Render(heading))
-			sb.WriteRune('\n')
 		}
-	}
 
+		if category != currentCategory {
+			currentCategory = category
+			fmt.Fprintf(sb, "%s\n", categoryStyle.Render(currentCategory))
+		}
+
+		tstyle := titleStyle
+		if c.conv.Title == "" {
+			tstyle = untitledStyle
+		}
+		heading := fmt.Sprintf(
+			"%s\n%s",
+			tstyle.Render(c.conv.Title),
+			ageStyle.Render(util.HumanTimeElapsedSince(lastReplyAge)),
+		)
+		sb.WriteString(conversationHeadingStyle.Render(heading))
+		sb.WriteRune('\n')
+	}
 	return sb.String()
 }