diff --git a/app/src/main/java/eu/kanade/tachiyomi/ui/history/HistoryScreenModel.kt b/app/src/main/java/eu/kanade/tachiyomi/ui/history/HistoryScreenModel.kt
index 7b0cdcf72..c0c2b555f 100644
--- a/app/src/main/java/eu/kanade/tachiyomi/ui/history/HistoryScreenModel.kt
+++ b/app/src/main/java/eu/kanade/tachiyomi/ui/history/HistoryScreenModel.kt
@@ -28,7 +28,6 @@ import tachiyomi.domain.history.interactor.RemoveHistory
 import tachiyomi.domain.history.model.HistoryWithRelations
 import uy.kohesive.injekt.Injekt
 import uy.kohesive.injekt.api.get
-import java.time.LocalDate
 
 class HistoryScreenModel(
     private val getHistory: GetHistory = Injekt.get(),
@@ -60,12 +59,10 @@ class HistoryScreenModel(
     private fun List<HistoryWithRelations>.toHistoryUiModels(): List<HistoryUiModel> {
         return map { HistoryUiModel.Item(it) }
             .insertSeparators { before, after ->
-                val beforeDate = before?.item?.readAt?.time?.toLocalDate() ?: LocalDate.MIN
-                val afterDate = after?.item?.readAt?.time?.toLocalDate() ?: LocalDate.MIN
+                val beforeDate = before?.item?.readAt?.time?.toLocalDate()
+                val afterDate = after?.item?.readAt?.time?.toLocalDate()
                 when {
-                    beforeDate.isAfter(afterDate)
-                        or afterDate.equals(LocalDate.MIN)
-                        or beforeDate.equals(LocalDate.MIN) -> HistoryUiModel.Header(afterDate)
+                    beforeDate != afterDate && afterDate != null -> HistoryUiModel.Header(afterDate)
                     // Return null to avoid adding a separator between two items.
                     else -> null
                 }
diff --git a/app/src/main/java/eu/kanade/tachiyomi/ui/updates/UpdatesScreenModel.kt b/app/src/main/java/eu/kanade/tachiyomi/ui/updates/UpdatesScreenModel.kt
index 2b2c1c25a..c5385d1f0 100644
--- a/app/src/main/java/eu/kanade/tachiyomi/ui/updates/UpdatesScreenModel.kt
+++ b/app/src/main/java/eu/kanade/tachiyomi/ui/updates/UpdatesScreenModel.kt
@@ -45,7 +45,6 @@ import tachiyomi.domain.updates.interactor.GetUpdates
 import tachiyomi.domain.updates.model.UpdatesWithRelations
 import uy.kohesive.injekt.Injekt
 import uy.kohesive.injekt.api.get
-import java.time.LocalDate
 import java.time.ZonedDateTime
 
 class UpdatesScreenModel(
@@ -374,12 +373,10 @@ class UpdatesScreenModel(
             return items
                 .map { UpdatesUiModel.Item(it) }
                 .insertSeparators { before, after ->
-                    val beforeDate = before?.item?.update?.dateFetch?.toLocalDate() ?: LocalDate.MIN
-                    val afterDate = after?.item?.update?.dateFetch?.toLocalDate() ?: LocalDate.MIN
+                    val beforeDate = before?.item?.update?.dateFetch?.toLocalDate()
+                    val afterDate = after?.item?.update?.dateFetch?.toLocalDate()
                     when {
-                        beforeDate.isAfter(afterDate)
-                            or afterDate.equals(LocalDate.MIN)
-                            or beforeDate.equals(LocalDate.MIN) -> UpdatesUiModel.Header(afterDate)
+                        beforeDate != afterDate && afterDate != null -> UpdatesUiModel.Header(afterDate)
                         // Return null to avoid adding a separator between two items.
                         else -> null
                     }
diff --git a/app/src/main/java/eu/kanade/tachiyomi/util/lang/DateExtensions.kt b/app/src/main/java/eu/kanade/tachiyomi/util/lang/DateExtensions.kt
index 9e61555ec..8326fe2f8 100644
--- a/app/src/main/java/eu/kanade/tachiyomi/util/lang/DateExtensions.kt
+++ b/app/src/main/java/eu/kanade/tachiyomi/util/lang/DateExtensions.kt
@@ -13,6 +13,7 @@ import java.time.format.DateTimeFormatter
 import java.time.format.FormatStyle
 import java.time.temporal.ChronoUnit
 import java.util.Date
+import kotlin.math.absoluteValue
 
 fun LocalDateTime.toDateTimestampString(dateTimeFormatter: DateTimeFormatter): String {
     val date = dateTimeFormatter.format(this)
@@ -49,13 +50,20 @@ fun LocalDate.toRelativeString(
     val now = LocalDate.now()
     val difference = ChronoUnit.DAYS.between(this, now)
     return when {
-        difference < 0 -> difference.toString()
+        difference < -7 -> dateFormat.format(this)
+        difference < 0 -> context.pluralStringResource(
+            MR.plurals.upcoming_relative_time,
+            difference.toInt().absoluteValue,
+            difference.toInt().absoluteValue,
+        )
+
         difference < 1 -> context.stringResource(MR.strings.relative_time_today)
         difference < 7 -> context.pluralStringResource(
             MR.plurals.relative_time,
             difference.toInt(),
             difference.toInt(),
         )
+
         else -> dateFormat.format(this)
     }
 }
diff --git a/i18n/src/commonMain/resources/MR/base/plurals.xml b/i18n/src/commonMain/resources/MR/base/plurals.xml
index 2f10b004c..d9c958afc 100644
--- a/i18n/src/commonMain/resources/MR/base/plurals.xml
+++ b/i18n/src/commonMain/resources/MR/base/plurals.xml
@@ -10,6 +10,11 @@
         <item quantity="other">%1$d days ago</item>
     </plurals>
 
+    <plurals name="upcoming_relative_time">
+        <item quantity="one">Tomorrow</item>
+        <item quantity="other">In %1$d days</item>
+    </plurals>
+
     <plurals name="num_categories">
         <item quantity="one">%d category</item>
         <item quantity="other">%d categories</item>