diff --git a/public/script.js b/public/script.js
index bfe9fe57d..3b3de2e7e 100644
--- a/public/script.js
+++ b/public/script.js
@@ -3548,7 +3548,7 @@ export function getBiasStrings(textareaText, type) {
  */
 function formatMessageHistoryItem(chatItem, isInstruct, forceOutputSequence) {
     const isNarratorType = chatItem?.extra?.type === system_message_types.NARRATOR;
-    const characterName = (selected_group || chatItem.force_avatar) ? chatItem.name : name2;
+    const characterName = chatItem?.name ? chatItem.name : name2;
     const itemName = chatItem.is_user ? chatItem['name'] : characterName;
     const shouldPrependName = !isNarratorType;
 
diff --git a/public/scripts/extensions/expressions/index.js b/public/scripts/extensions/expressions/index.js
index aa1b40def..627742b73 100644
--- a/public/scripts/extensions/expressions/index.js
+++ b/public/scripts/extensions/expressions/index.js
@@ -1,4 +1,4 @@
-import { callPopup, eventSource, event_types, getRequestHeaders, saveSettingsDebounced } from "../../../script.js";
+import { callPopup, eventSource, event_types, getRequestHeaders, saveSettingsDebounced, this_chid } from "../../../script.js";
 import { dragElement, isMobile } from "../../RossAscends-mods.js";
 import { getContext, getApiUrl, modules, extension_settings, ModuleWorkerWrapper, doExtrasFetch, renderExtensionTemplate } from "../../extensions.js";
 import { loadMovingUIState, power_user } from "../../power-user.js";
@@ -493,24 +493,6 @@ async function moduleWorker() {
         return;
     }
 
-    // character changed
-    if (context.groupId !== lastCharacter && context.characterId !== lastCharacter) {
-        removeExpression();
-        spriteCache = {};
-
-        //clear expression
-        let imgElement = document.getElementById('expression-image');
-        if (imgElement && imgElement instanceof HTMLImageElement) {
-            imgElement.src = "";
-        }
-
-        //set checkbox to global var
-        $('#image_type_toggle').prop('checked', extension_settings.expressions.talkinghead);
-        if (extension_settings.expressions.talkinghead) {
-            setTalkingHeadState(extension_settings.expressions.talkinghead);
-        }
-    }
-
     const vnMode = isVisualNovelMode();
     const vnWrapperVisible = $('#visual-novel-wrapper').is(':visible');
 
@@ -531,7 +513,7 @@ async function moduleWorker() {
     }
 
     const currentLastMessage = getLastCharacterMessage();
-    let spriteFolderName = getSpriteFolderName(currentLastMessage, currentLastMessage.name);
+    let spriteFolderName = context.groupId ? getSpriteFolderName(currentLastMessage, currentLastMessage.name) : getSpriteFolderName();
 
     // character has no expressions or it is not loaded
     if (Object.keys(spriteCache).length === 0) {
@@ -1492,6 +1474,25 @@ function setExpressionOverrideHtml(forceClear = false) {
     moduleWorker();
     dragElement($("#expression-holder"))
     eventSource.on(event_types.CHAT_CHANGED, () => {
+        // character changed
+        const context = getContext();
+        if (context.groupId !== lastCharacter && context.characterId !== lastCharacter) {
+            removeExpression();
+            spriteCache = {};
+
+            //clear expression
+            let imgElement = document.getElementById('expression-image');
+            if (imgElement && imgElement instanceof HTMLImageElement) {
+                imgElement.src = "";
+            }
+
+            //set checkbox to global var
+            $('#image_type_toggle').prop('checked', extension_settings.expressions.talkinghead);
+            if (extension_settings.expressions.talkinghead) {
+                setTalkingHeadState(extension_settings.expressions.talkinghead);
+            }
+        }
+
         setExpressionOverrideHtml();
 
         if (isVisualNovelMode()) {
diff --git a/public/scripts/slash-commands.js b/public/scripts/slash-commands.js
index fd65cae34..861bbe0c5 100644
--- a/public/scripts/slash-commands.js
+++ b/public/scripts/slash-commands.js
@@ -21,9 +21,12 @@ import {
     reloadCurrentChat,
     sendMessageAsUser,
     name1,
+    Generate,
+    this_chid,
+    setCharacterName,
 } from "../script.js";
 import { getMessageTimeStamp } from "./RossAscends-mods.js";
-import { resetSelectedGroup } from "./group-chats.js";
+import { resetSelectedGroup, selected_group } from "./group-chats.js";
 import { getRegexedString, regex_placement } from "./extensions/regex/engine.js";
 import { chat_styles, power_user } from "./power-user.js";
 import { autoSelectPersona } from "./personas.js";
@@ -131,6 +134,7 @@ parser.addCommand('flat', setFlatModeCallback, ['default'], ' – sets the messa
 parser.addCommand('continue', continueChatCallback, ['cont'], ' – continues the last message in the chat', true, true);
 parser.addCommand('go', goToCharacterCallback, ['char'], '<span class="monospace">(name)</span> – opens up a chat with the character by its name', true, true);
 parser.addCommand('sysgen', generateSystemMessage, [], '<span class="monospace">(prompt)</span> – generates a system message using a specified prompt', true, true);
+parser.addCommand('ask', askCharacter, [], '<span class="monospace">(prompt)</span> – asks a specified character card a prompt', true, true);
 parser.addCommand('delname', deleteMessagesByNameCallback, ['cancel'], '<span class="monospace">(name)</span> – deletes all messages attributed to a specified name', true, true);
 parser.addCommand('send', sendUserMessageCallback, ['add'], '<span class="monospace">(text)</span> – adds a user message to the chat log without triggering a generation', true, true);
 
@@ -138,6 +142,88 @@ const NARRATOR_NAME_KEY = 'narrator_name';
 const NARRATOR_NAME_DEFAULT = 'System';
 export const COMMENT_NAME_DEFAULT = 'Note';
 
+async function askCharacter(_, text) {
+    // Prevent generate recursion
+    $('#send_textarea').val('');
+
+    // Not supported in group chats
+    // TODO: Maybe support group chats?
+    if (selected_group) {
+        toastr.error("Cannot run this command in a group chat!");
+        return;
+    }
+
+    if (!text) {
+        console.warn('WARN: No text provided for /ask command')
+    }
+
+    const parts = text.split('\n');
+    if (parts.length <= 1) {
+        toastr.warning('Both character name and message are required. Separate them with a new line.');
+        return;
+    }
+
+    // Grabbing the message
+    const name = parts.shift().trim();
+    let mesText = parts.join('\n').trim();
+    const prevChId = this_chid;
+
+    // Find the character
+    const chId = characters.findIndex((e) => e.name === name);
+    if (!characters[chId] || chId === -1) {
+        toastr.error("Character not found.");
+        return;
+    }
+
+    // Override character and send a user message
+    setCharacterId(chId);
+
+    // TODO: Maybe look up by filename instead of name
+    const character = characters[chId];
+    let force_avatar, original_avatar;
+
+    if (character && character.avatar !== 'none') {
+        force_avatar = getThumbnailUrl('avatar', character.avatar);
+        original_avatar = character.avatar;
+    }
+    else {
+        force_avatar = default_avatar;
+        original_avatar = default_avatar;
+    }
+
+    setCharacterName(character.name);
+
+    sendMessageAsUser(mesText)
+
+    const restoreCharacter = () => {
+        setCharacterId(prevChId);
+        setCharacterName(characters[prevChId].name);
+
+        // Only force the new avatar if the character name is the same
+        // This skips if an error was fired
+        const lastMessage = chat[chat.length - 1];
+        if (lastMessage && lastMessage?.name === character.name) {
+            lastMessage.force_avatar = force_avatar;
+            lastMessage.original_avatar = original_avatar;
+        }
+
+        // Kill this callback once the event fires
+        eventSource.removeListener(event_types.CHARACTER_MESSAGE_RENDERED, restoreCharacter)
+    }
+
+    // Run generate and restore previous character on error
+    try {
+        toastr.info(`Asking ${character.name} something...`);
+        await Generate('ask_command')
+    } catch {
+        restoreCharacter()
+    }
+
+    // Restore previous character once message renders
+    // Hack for generate
+    eventSource.on(event_types.CHARACTER_MESSAGE_RENDERED, restoreCharacter);
+}
+
 async function sendUserMessageCallback(_, text) {
     if (!text) {
         console.warn('WARN: No text provided for /send command');