diff --git a/api/src/party-types.ts b/api/src/party-types.ts
index 9117a1c..427092e 100644
--- a/api/src/party-types.ts
+++ b/api/src/party-types.ts
@@ -36,6 +36,8 @@ type BaseQuestion = {
 	points: number;
 	song?: Song;
 	hideSongTitle?: boolean;
+	questionKey?: string;
+	subjectKey?: string;
 };
 
 export type Question =
diff --git a/api/src/party/__tests__/question-generation.test.ts b/api/src/party/__tests__/question-generation.test.ts
new file mode 100644
index 0000000..8ba70d5
--- /dev/null
+++ b/api/src/party/__tests__/question-generation.test.ts
@@ -0,0 +1,208 @@
+import { describe, expect, it, vi } from "vitest";
+import type { Question, QuizRound } from "../../party-types";
+import { buildNumericQuestion } from "../numeric-question-generator";
+import {
+	buildMemberOptions,
+	type PartyAnalytics,
+	type PartyQuestionMember,
+	pickQuestionCandidate,
+} from "../question-utils";
+import { buildSocialQuestion } from "../social-question-generator";
+
+type Db = typeof import("../../db").db;
+
+function makeChoiceQuestion(
+	text: string,
+	key: string,
+	subjectKey: string,
+): Question {
+	return {
+		type: "choice",
+		text,
+		correct: 0,
+		startTimestamp: 1,
+		endTimestamp: 2,
+		points: 10,
+		options: ["A", "B"],
+		questionKey: key,
+		subjectKey,
+	};
+}
+
+function createFakeDb(trackReleaseDate: Date | null) {
+	const trackRecord = {
+		id: "track-1",
+		name: "Shared Track",
+		album: {
+			name: "Shared Album",
+			release_date: trackReleaseDate,
+		},
+		artists: [{ id: "artist-1", name: "Shared Artist" }],
+	};
+
+	return {
+		query: {
+			track: {
+				findFirst: vi.fn(async () => trackRecord),
+				findMany: vi.fn(async () => []),
+			},
+			artist: {
+				findFirst: vi.fn(async () => ({
+					id: "artist-1",
+					name: "Shared Artist",
+				})),
+			},
+		},
+		select: vi.fn(() => ({
+			from: () => ({
+				where: async () => [],
+			}),
+		})),
+	} as unknown as Db;
+}
+
+describe("question generation", () => {
+	it("skips repeated question keys, subjects, and text", () => {
+		const history: QuizRound[] = [
+			{
+				questionIndex: 0,
+				question: {
+					...makeChoiceQuestion(
+						"Which genre appears most in the party analytics?",
+						"audio:genre:pop",
+						"genre:pop",
+					),
+				},
+				responses: [],
+			},
+		];
+
+		const question = pickQuestionCandidate(
+			[
+				{
+					key: "audio:genre:pop",
+					subjectKey: "genre:pop",
+					question: makeChoiceQuestion(
+						"Which genre appears most in the party analytics?",
+						"audio:genre:pop",
+						"genre:pop",
+					),
+				},
+				{
+					key: "audio:artist:abba",
+					subjectKey: "artist:abba",
+					question: makeChoiceQuestion(
+						"Which artist shows up most often in the shared audio data?",
+						"audio:artist:abba",
+						"artist:abba",
+					),
+				},
+			],
+			history,
+			0,
+		);
+
+		expect(question?.text).toBe(
+			"Which artist shows up most often in the shared audio data?",
+		);
+	});
+
+	it("returns null when member options would require fake placeholders", () => {
+		const members: PartyQuestionMember[] = [
+			{ userId: "a", name: "Sam" },
+			{ userId: "b", name: "Sam" },
+		];
+
+		const correctMember = members[0];
+		expect(correctMember).toBeDefined();
+		if (correctMember) {
+			expect(buildMemberOptions(correctMember, members)).toBeNull();
+		}
+	});
+
+	it("skips numeric questions with missing release dates and zero counts", async () => {
+		const db = createFakeDb(null);
+		const analytics = {
+			storyClusters: [
+				{
+					tracks: [
+						{
+							name: "Shared Track",
+							artists: [{ name: "Shared Artist" }],
+							albumName: "Shared Album",
+						},
+					],
+					artists: [{ name: "Shared Artist" }],
+					genres: [],
+				},
+			],
+			groupSummary: {
+				mostSharedGenres: [],
+			},
+		} as PartyAnalytics;
+		const members: PartyQuestionMember[] = [
+			{ userId: "a", name: "A" },
+			{ userId: "b", name: "B" },
+		];
+		const history: QuizRound[] = [
+			{
+				questionIndex: 0,
+				question: {
+					type: "numeric",
+					text: "What's the release year of Shared Album?",
+					correct: 2010,
+					startTimestamp: 1,
+					endTimestamp: 2,
+					points: 10,
+					range: { min: 2000, max: 2010 },
+					questionKey: "numeric:album-year:Shared Album",
+					subjectKey: "album:Shared Album",
+				},
+				responses: [],
+			},
+		];
+
+		const question = await buildNumericQuestion({
+			db,
+			analytics,
+			index: 0,
+			members,
+			history,
+		});
+
+		expect(question).toBeNull();
+	});
+
+	it("skips social fallback names for duplicate members", async () => {
+		const db = createFakeDb(null);
+		const members: PartyQuestionMember[] = [
+			{ userId: "a", name: "Sam" },
+			{ userId: "b", name: "Sam" },
+		];
+		const quizState = {
+			status: "running" as const,
+			workflowId: null,
+			questionIndex: 0,
+			currentQuestion: null,
+			answers: {},
+			scores: { a: 3, b: 1 },
+			history: [],
+		};
+
+		const question = await buildSocialQuestion(
+			db,
+			quizState,
+			{
+				groupSummary: {
+					mostDiverseMember: { userId: "a", genreEntropy: 1 },
+					mostSharedGenres: [],
+					mostAlignedPair: null,
+				},
+			},
+			members,
+			0,
+		);
+
+		expect(question).toBeNull();
+	});
+});
diff --git a/api/src/party/audio-question-generator.ts b/api/src/party/audio-question-generator.ts
index 3bcb4c5..3425130 100644
--- a/api/src/party/audio-question-generator.ts
+++ b/api/src/party/audio-question-generator.ts
@@ -1,5 +1,5 @@
 import type { db as Db } from "../db";
-import type { Question } from "../party-types";
+import type { Question, QuizRound } from "../party-types";
 import {
 	buildOptionsWithCorrect,
 	buildOrderedOptions,
@@ -9,7 +9,9 @@ import {
 	getTopClusterTracks,
 	isUsableText,
 	type PartyAnalytics,
+	pickQuestionCandidate,
 	pickRandom,
+	type QuestionCandidate,
 	resolveQuestionSong,
 } from "./question-utils";
 
@@ -17,10 +19,11 @@ export async function buildAudioMetadataQuestion(
 	dbClient: typeof Db,
 	analytics: PartyAnalytics,
 	index: number,
+	history: QuizRound[],
 ): Promise<Question | null> {
 	type ChoiceQuestion = Extract<Question, { type: "choice" }>;
 	const questions: Array<
-		Omit<ChoiceQuestion, "startTimestamp" | "endTimestamp">
+		QuestionCandidate<Omit<ChoiceQuestion, "startTimestamp" | "endTimestamp">>
 	> = [];
 	const topSong = await resolveQuestionSong(dbClient, analytics);
 	const topSongName = topSong?.name;
@@ -34,13 +37,17 @@ export async function buildAudioMetadataQuestion(
 		);
 		if (currentSongOptions) {
 			questions.push({
-				type: "choice",
-				text: "What song is currently playing?",
-				options: currentSongOptions,
-				correct: 0,
-				points: 10,
-				song: topSong ?? undefined,
-				hideSongTitle: true,
+				key: `audio:current-song:${topSongName}`,
+				subjectKey: `track:${topSongName}`,
+				question: {
+					type: "choice",
+					text: "What song is currently playing?",
+					options: currentSongOptions,
+					correct: 0,
+					points: 10,
+					song: topSong ?? undefined,
+					hideSongTitle: true,
+				},
 			});
 		}
 	}
@@ -50,14 +57,21 @@ export async function buildAudioMetadataQuestion(
 		4,
 	);
 	if (genreOptions) {
-		questions.push({
-			type: "choice",
-			text: "Which genre appears most in the party analytics?",
-			options: genreOptions,
-			correct: 0,
-			points: 10,
-			song: topSong ?? undefined,
-		});
+		const topGenre = genreOptions[0];
+		if (topGenre) {
+			questions.push({
+				key: `audio:genre:${topGenre}`,
+				subjectKey: `genre:${topGenre}`,
+				question: {
+					type: "choice",
+					text: "Which genre appears most in the party analytics?",
+					options: genreOptions,
+					correct: 0,
+					points: 10,
+					song: topSong ?? undefined,
+				},
+			});
+		}
 	}
 
 	const topArtists = getTopClusterArtists(analytics);
@@ -66,12 +80,16 @@ export async function buildAudioMetadataQuestion(
 		const artistOptions = buildOptionsWithCorrect(topArtist, topArtists, 4);
 		if (artistOptions) {
 			questions.push({
-				type: "choice",
-				text: "Which artist shows up most often in the shared audio data?",
-				options: artistOptions,
-				correct: 0,
-				points: 10,
-				song: topSong ?? undefined,
+				key: `audio:artist:${topArtist}`,
+				subjectKey: `artist:${topArtist}`,
+				question: {
+					type: "choice",
+					text: "Which artist shows up most often in the shared audio data?",
+					options: artistOptions,
+					correct: 0,
+					points: 10,
+					song: topSong ?? undefined,
+				},
 			});
 		}
 	}
@@ -83,12 +101,16 @@ export async function buildAudioMetadataQuestion(
 			: null;
 		if (trackOptions) {
 			questions.push({
-				type: "choice",
-				text: "Which track looks most shared across the party?",
-				options: trackOptions,
-				correct: 0,
-				points: 10,
-				song: topSong ?? undefined,
+				key: `audio:track:${topTrackName}`,
+				subjectKey: `track:${topTrackName}`,
+				question: {
+					type: "choice",
+					text: "Which track looks most shared across the party?",
+					options: trackOptions,
+					correct: 0,
+					points: 10,
+					song: topSong ?? undefined,
+				},
 			});
 		}
 	}
@@ -112,12 +134,16 @@ export async function buildAudioMetadataQuestion(
 			);
 			if (artistOptions) {
 				questions.push({
-					type: "choice",
-					text: `Who performs "${randomTopTrack.name}"?`,
-					options: artistOptions,
-					correct: 0,
-					points: 10,
-					song: randomTrackSong ?? topSong ?? undefined,
+					key: `audio:performer:${randomTopTrack.name}`,
+					subjectKey: `track:${randomTopTrack.name}`,
+					question: {
+						type: "choice",
+						text: `Who performs "${randomTopTrack.name}"?`,
+						options: artistOptions,
+						correct: 0,
+						points: 10,
+						song: randomTrackSong ?? topSong ?? undefined,
+					},
 				});
 			}
 
@@ -129,13 +155,16 @@ export async function buildAudioMetadataQuestion(
 			);
 			if (trackNameOptions) {
 				questions.push({
-					type: "choice",
-					text: `What is the name of this track by ${correctArtist}?`,
-					options: trackNameOptions,
-					correct: 0,
-					points: 10,
-					song: randomTrackSong ?? topSong ?? undefined,
-					hideSongTitle: true,
+					key: `audio:title:${randomTopTrack.name}`,
+					subjectKey: `track:${randomTopTrack.name}`,
+					question: {
+						type: "choice",
+						text: `What is the name of this track by ${correctArtist}?`,
+						options: trackNameOptions,
+						correct: 0,
+						points: 10,
+						song: randomTrackSong ?? topSong ?? undefined,
+					},
 				});
 			}
 
@@ -147,13 +176,17 @@ export async function buildAudioMetadataQuestion(
 				);
 				if (alternateSongOptions) {
 					questions.push({
-						type: "choice",
-						text: "Which song is this audio clip from?",
-						options: alternateSongOptions,
-						correct: 0,
-						points: 10,
-						song: topSong ?? undefined,
-						hideSongTitle: true,
+						key: `audio:current-song:${topSongName}`,
+						subjectKey: `track:${topSongName}`,
+						question: {
+							type: "choice",
+							text: "Which song is this audio clip from?",
+							options: alternateSongOptions,
+							correct: 0,
+							points: 10,
+							song: topSong ?? undefined,
+							hideSongTitle: true,
+						},
 					});
 				}
 			}
@@ -170,12 +203,16 @@ export async function buildAudioMetadataQuestion(
 			);
 			if (albumOptions) {
 				questions.push({
-					type: "choice",
-					text: `"${randomTopTrack.name}" appears on which album?`,
-					options: albumOptions,
-					correct: 0,
-					points: 10,
-					song: randomTrackSong ?? topSong ?? undefined,
+					key: `audio:album:${randomTopTrack.albumName}`,
+					subjectKey: `track:${randomTopTrack.name}`,
+					question: {
+						type: "choice",
+						text: `"${randomTopTrack.name}" appears on which album?`,
+						options: albumOptions,
+						correct: 0,
+						points: 10,
+						song: randomTrackSong ?? topSong ?? undefined,
+					},
 				});
 			}
 		}
@@ -185,7 +222,7 @@ export async function buildAudioMetadataQuestion(
 		return null;
 	}
 
-	const question = questions[index % questions.length];
-	if (!question) throw new Error("Question not found");
+	const question = pickQuestionCandidate(questions, history, index);
+	if (!question) return null;
 	return buildQuestionWindow(question);
 }
diff --git a/api/src/party/numeric-question-generator.ts b/api/src/party/numeric-question-generator.ts
index 4f8723a..11c63f9 100644
--- a/api/src/party/numeric-question-generator.ts
+++ b/api/src/party/numeric-question-generator.ts
@@ -4,13 +4,15 @@ import {
 	topArtist as topArtistTable,
 	topTrack as topTrackTable,
 } from "../db/schema";
-import type { Question } from "../party-types";
+import type { Question, QuizRound } from "../party-types";
 import {
 	buildQuestionWindow,
 	getReleaseYearRange,
 	isUsableText,
 	type PartyAnalytics,
 	type PartyQuestionMember,
+	pickQuestionCandidate,
+	type QuestionCandidate,
 	resolveQuestionSong,
 } from "./question-utils";
 
@@ -24,12 +26,12 @@ type BuildNumericQuestionInput = {
 	analytics: PartyAnalytics;
 	index: number;
 	members: PartyQuestionMember[];
+	history: QuizRound[];
 };
 
 async function getAlbumReleaseYear({
 	db,
 	analytics,
-	index,
 }: BuildNumericQuestionInput): Promise<NumericQuestion | null> {
 	const trackName = analytics?.storyClusters?.[0]?.tracks?.[0]?.name;
 	const track = trackName
@@ -38,16 +40,15 @@ async function getAlbumReleaseYear({
 				with: { album: true },
 			})
 		: null;
-	const song = await resolveQuestionSong(db, analytics, {
-		trackName: track?.name ?? trackName ?? undefined,
-	});
 	const subject = [track?.album?.name, track?.name].find((value) =>
 		isUsableText(value),
 	);
 	if (!subject) return null;
-	const correct =
-		track?.album?.release_date?.getFullYear() ??
-		new Date().getFullYear() - 1 - index;
+	if (!track?.album?.release_date) return null;
+	const song = await resolveQuestionSong(db, analytics, {
+		trackName: track?.name ?? trackName ?? undefined,
+	});
+	const correct = track.album.release_date.getFullYear();
 	return {
 		type: "numeric",
 		text: `What's the release year of ${subject}?`,
@@ -55,6 +56,8 @@ async function getAlbumReleaseYear({
 		range: getReleaseYearRange(correct),
 		points: 10,
 		song: song ?? undefined,
+		questionKey: `numeric:album-year:${subject}`,
+		subjectKey: `album:${subject}`,
 	};
 }
 
@@ -81,6 +84,7 @@ async function countTopTrackListeners({
 			),
 		);
 	const correct = new Set(entries.map((e) => e.userId)).size;
+	if (correct <= 0) return null;
 	return {
 		type: "numeric",
 		text: `For how many players in the party is "${trackName}" a top track?`,
@@ -88,6 +92,8 @@ async function countTopTrackListeners({
 		range: { min: 0, max: members.length },
 		points: 10,
 		song: song ?? undefined,
+		questionKey: `numeric:top-track-count:${trackName}`,
+		subjectKey: `track:${trackName}`,
 	};
 }
 
@@ -116,6 +122,7 @@ async function countFavouriteArtistListeners({
 			),
 		);
 	const correct = new Set(entries.map((e) => e.userId)).size;
+	if (correct <= 0) return null;
 	return {
 		type: "numeric",
 		text: `How many players in the party have "${artistName}" as a favourite artist?`,
@@ -123,24 +130,44 @@ async function countFavouriteArtistListeners({
 		range: { min: 0, max: members.length },
 		points: 10,
 		song: song ?? undefined,
+		questionKey: `numeric:artist-count:${artistName}`,
+		subjectKey: `artist:${artistName}`,
 	};
 }
 
 export async function buildNumericQuestion(
 	input: BuildNumericQuestionInput,
 ): Promise<Question | null> {
-	const questions: NumericQuestion[] = [];
+	const questions: Array<QuestionCandidate<NumericQuestion>> = [];
 
 	const albumYearQ = await getAlbumReleaseYear(input);
-	if (albumYearQ) questions.push(albumYearQ);
+	if (albumYearQ) {
+		questions.push({
+			key: albumYearQ.questionKey ?? `numeric:album-year:${albumYearQ.text}`,
+			subjectKey: albumYearQ.subjectKey,
+			question: albumYearQ,
+		});
+	}
 
 	const topTrackQ = await countTopTrackListeners(input);
-	if (topTrackQ) questions.push(topTrackQ);
+	if (topTrackQ) {
+		questions.push({
+			key: topTrackQ.questionKey ?? `numeric:top-track-count:${topTrackQ.text}`,
+			subjectKey: topTrackQ.subjectKey,
+			question: topTrackQ,
+		});
+	}
 
 	const artistQ = await countFavouriteArtistListeners(input);
-	if (artistQ) questions.push(artistQ);
+	if (artistQ) {
+		questions.push({
+			key: artistQ.questionKey ?? `numeric:artist-count:${artistQ.text}`,
+			subjectKey: artistQ.subjectKey,
+			question: artistQ,
+		});
+	}
 
-	const question = questions[input.index % questions.length] ?? questions[0];
+	const question = pickQuestionCandidate(questions, input.history, input.index);
 	if (!question) return null;
 	return buildQuestionWindow(question);
 }
diff --git a/api/src/party/question-generator.ts b/api/src/party/question-generator.ts
index 08dd9fc..0a65f27 100644
--- a/api/src/party/question-generator.ts
+++ b/api/src/party/question-generator.ts
@@ -3,7 +3,7 @@ import type { Question, QuizState } from "../party-types";
 import { buildAudioMetadataQuestion } from "./audio-question-generator";
 import { buildNumericQuestion } from "./numeric-question-generator";
 import type { PartyAnalytics } from "./question-utils";
-import { fetchPartyMembers } from "./question-utils";
+import { buildQuestionWindow, fetchPartyMembers } from "./question-utils";
 import { buildSocialQuestion } from "./social-question-generator";
 
 export type PartyQuestionType = "audio-metadata" | "social" | "numeric";
@@ -24,21 +24,58 @@ export async function generatePartyQuestion({
 	index,
 }: GenerateQuestionInput): Promise<Question | null> {
 	const members = await fetchPartyMembers(dbClient, partyId);
-	const type: PartyQuestionType =
-		index === 2 ? "numeric" : index % 2 === 0 ? "audio-metadata" : "social";
+	const preferredOrder: PartyQuestionType[] = [
+		"audio-metadata",
+		"social",
+		"numeric",
+	];
+	const rotation = index % preferredOrder.length;
+	const typeOrder = [
+		...preferredOrder.slice(rotation),
+		...preferredOrder.slice(0, rotation),
+	];
+
+	for (const type of typeOrder) {
+		if (type === "audio-metadata") {
+			const q = await buildAudioMetadataQuestion(
+				dbClient,
+				analytics,
+				index,
+				quizState.history,
+			);
+			if (q) return q;
+			continue;
+		}
+
+		if (type === "social") {
+			const q = await buildSocialQuestion(
+				dbClient,
+				quizState,
+				analytics,
+				members,
+				index,
+			);
+			if (q) return q;
+			continue;
+		}
 
-	if (type === "audio-metadata") {
-		const q = await buildAudioMetadataQuestion(dbClient, analytics, index);
-		if (q) return q;
-	}
-	if (type === "numeric") {
 		const q = await buildNumericQuestion({
 			db: dbClient,
 			analytics,
 			index,
 			members,
+			history: quizState.history,
 		});
 		if (q) return q;
 	}
-	return buildSocialQuestion(dbClient, quizState, analytics, members, index);
+
+	return buildQuestionWindow({
+		type: "numeric" as const,
+		text: "How many players are in this party?",
+		correct: members.length,
+		range: { min: 0, max: members.length },
+		points: 5,
+		subjectKey: "party-size",
+		questionKey: `fallback:party-size:${members.length}`,
+	});
 }
diff --git a/api/src/party/question-utils.ts b/api/src/party/question-utils.ts
index 14fe0d8..b65873e 100644
--- a/api/src/party/question-utils.ts
+++ b/api/src/party/question-utils.ts
@@ -1,6 +1,7 @@
 import type { InferSelectModel } from "drizzle-orm";
 import type { db as Db } from "../db";
 import type { track as trackTable } from "../db/schema";
+import type { QuizRound } from "../party-types";
 
 export type PartyQuestionMember = {
 	userId: string;
@@ -9,7 +10,14 @@ export type PartyQuestionMember = {
 
 export type PartyAnalytics = {
 	groupSummary?: {
+		totalMembers?: number;
 		mostSharedGenres?: { name: string }[];
+		mostDiverseMember?: { userId: string; genreEntropy: number } | null;
+		mostAlignedPair?: {
+			userIdA: string;
+			userIdB: string;
+			similarity?: number;
+		} | null;
 	};
 	storyClusters?: {
 		tracks?: {
@@ -31,6 +39,17 @@ export type AnalyticsTrack = {
 	albumName?: string;
 	memberScores?: { userId: string; score: number }[];
 };
+type QuestionLike = {
+	text: string;
+	questionKey?: string;
+	subjectKey?: string;
+};
+
+export type QuestionCandidate<T extends QuestionLike = QuestionLike> = {
+	key: string;
+	subjectKey?: string;
+	question: T;
+};
 export type QuestionSong = InferSelectModel<typeof trackTable>;
 
 export const QUESTION_DURATION_MS = 60_000;
@@ -113,6 +132,46 @@ export function getMostSharedGenreNames(analytics: PartyAnalytics): string[] {
 	);
 }
 
+export function pickQuestionCandidate<T extends QuestionLike>(
+	candidates: QuestionCandidate<T>[],
+	history: QuizRound[],
+	index: number,
+): T | null {
+	const seenKeys = new Set<string>();
+	const seenSubjects = new Set<string>();
+	const seenTexts = new Set<string>();
+
+	for (const round of history) {
+		const question = round.question;
+		seenTexts.add(normalizeQuestionKey(question.text));
+		if (question.questionKey)
+			seenKeys.add(normalizeQuestionKey(question.questionKey));
+		if (question.subjectKey)
+			seenSubjects.add(normalizeQuestionKey(question.subjectKey));
+	}
+
+	const fresh = candidates.filter((candidate) => {
+		const key = normalizeQuestionKey(candidate.key);
+		const subjectKey = candidate.subjectKey
+			? normalizeQuestionKey(candidate.subjectKey)
+			: null;
+		const text = normalizeQuestionKey(candidate.question.text);
+
+		if (seenKeys.has(key)) return false;
+		if (subjectKey && seenSubjects.has(subjectKey)) return false;
+		if (seenTexts.has(text)) return false;
+		return true;
+	});
+
+	if (fresh.length === 0) return null;
+	const pool = fresh;
+	return pool[index % pool.length]?.question ?? null;
+}
+
+function normalizeQuestionKey(value: string): string {
+	return value.trim().toLowerCase();
+}
+
 export function getTopClusterArtists(analytics: PartyAnalytics): string[] {
 	return (analytics?.storyClusters?.[0]?.artists ?? []).map(
 		(artist) => artist.name,
@@ -220,7 +279,7 @@ export function buildOrderedOptions(
 	desiredCount: number,
 ): string[] | null {
 	const options = uniqueStrings(
-		values.filter((value): value is string => Boolean(value)),
+		values.filter((value): value is string => isUsableText(value)),
 	);
 	return options.length >= desiredCount ? options.slice(0, desiredCount) : null;
 }
@@ -230,9 +289,10 @@ export function buildOptionsWithCorrect(
 	candidates: string[],
 	desiredCount: number,
 ): string[] | null {
+	if (!isUsableText(correct)) return null;
 	const options = uniqueStrings([
 		correct,
-		...candidates.filter((c) => c !== correct),
+		...candidates.filter((c) => isUsableText(c) && c !== correct),
 	]);
 	return options.length >= desiredCount ? options.slice(0, desiredCount) : null;
 }
@@ -271,43 +331,33 @@ export function hasClearLeader(quizState: {
 export function getMostDiverseMember(
 	analytics: PartyAnalytics,
 	members: PartyQuestionMember[],
-): PartyQuestionMember {
-	const userId = analytics?.memberProfiles?.[0]?.userId;
-	return (
-		members.find((member) => member.userId === userId) ??
-		members[1] ??
-		members[0] ?? { userId: "", name: "Player B" }
-	);
+): PartyQuestionMember | null {
+	const userId = analytics?.groupSummary?.mostDiverseMember?.userId;
+	if (!userId) return null;
+	return members.find((member) => member.userId === userId) ?? null;
 }
 
 export function getMostAlignedMember(
 	analytics: PartyAnalytics,
 	members: PartyQuestionMember[],
-): PartyQuestionMember {
-	const userId = analytics?.pairwise?.[0]?.userIdA;
-	return (
-		members.find((member) => member.userId === userId) ??
-		members[2] ??
-		members[0] ?? { userId: "", name: "Player C" }
-	);
+): PartyQuestionMember | null {
+	const userId = analytics?.groupSummary?.mostAlignedPair?.userIdA;
+	if (!userId) return null;
+	return members.find((member) => member.userId === userId) ?? null;
 }
 
 export function buildMemberOptions(
 	correctMember: PartyQuestionMember,
 	members: PartyQuestionMember[],
-): string[] {
+): string[] | null {
 	const desiredCount = getPartySize(members.length);
+	if (!isUsableText(correctMember.name)) return null;
 	const options = uniqueStrings([
 		correctMember.name,
-		...members.map((member) => member.name),
+		...members.map((member) => member.name).filter(isUsableText),
 	]);
 
-	if (options.length < desiredCount) {
-		for (const fallback of fallbackPlayerNames(desiredCount)) {
-			if (options.length >= desiredCount) break;
-			if (!options.includes(fallback)) options.push(fallback);
-		}
-	}
+	if (options.length < desiredCount) return null;
 
 	const ordered = [
 		correctMember.name,
@@ -328,27 +378,23 @@ function normalizeRange(
 	return { min: max, max: min };
 }
 
-function fallbackPlayerNames(count: number): string[] {
-	return Array.from(
-		{ length: count },
-		(_, index) => `Player ${String.fromCharCode(65 + index)}`,
-	);
-}
-
 export function buildMemberPairOptions(
 	members: PartyQuestionMember[],
 	correctPair: string,
 ): string[] | null {
 	if (members.length < 3) return null;
-	const pairs: string[] = [correctPair];
+	if (!isUsableText(correctPair)) return null;
+	const pairs = uniqueStrings([correctPair]);
 	for (let i = 0; i < members.length; i++) {
 		for (let j = i + 1; j < members.length; j++) {
 			const left = members[i];
 			const right = members[j];
 			if (!left || !right) continue;
+			if (!isUsableText(left.name) || !isUsableText(right.name)) continue;
 			const pair = `${left.name} & ${right.name}`;
 			if (pair !== correctPair) pairs.push(pair);
 		}
 	}
-	return pairs.length >= 2 ? pairs.slice(0, 4) : null;
+	const deduped = uniqueStrings(pairs);
+	return deduped.length >= 2 ? deduped.slice(0, 4) : null;
 }
diff --git a/api/src/party/social-question-generator.ts b/api/src/party/social-question-generator.ts
index 14e27ba..b2ebafa 100644
--- a/api/src/party/social-question-generator.ts
+++ b/api/src/party/social-question-generator.ts
@@ -5,14 +5,15 @@ import {
 	buildMemberPairOptions,
 	buildQuestionWindow,
 	getCurrentLeader,
-	getMostAlignedMember,
 	getMostDiverseMember,
 	getTopClusterTracks,
 	getTopTrackListener,
 	hasClearLeader,
 	type PartyAnalytics,
 	type PartyQuestionMember,
+	pickQuestionCandidate,
 	pickRandom,
+	type QuestionCandidate,
 	resolveQuestionSong,
 } from "./question-utils";
 
@@ -25,52 +26,49 @@ export async function buildSocialQuestion(
 ): Promise<Question | null> {
 	type ChoiceQuestion = Extract<Question, { type: "choice" }>;
 	const questions: Array<
-		Omit<ChoiceQuestion, "startTimestamp" | "endTimestamp">
+		QuestionCandidate<Omit<ChoiceQuestion, "startTimestamp" | "endTimestamp">>
 	> = [];
 	const topSong = await resolveQuestionSong(dbClient, analytics);
 
 	const hasMultipleMembers = members.length >= 2;
 	if (hasMultipleMembers && hasClearLeader(quizState)) {
 		const leader = getCurrentLeader(quizState, members);
-		questions.push({
-			type: "choice",
-			text: "Who is leading the quiz right now?",
-			options: buildMemberOptions(leader, members),
-			correct: 0,
-			points: 10,
-			song: topSong ?? undefined,
-		});
+		const options = buildMemberOptions(leader, members);
+		if (options) {
+			questions.push({
+				key: "social:leader",
+				subjectKey: `member:${leader.userId}`,
+				question: {
+					type: "choice",
+					text: "Who is leading the quiz right now?",
+					options,
+					correct: 0,
+					points: 10,
+					song: topSong ?? undefined,
+				},
+			});
+		}
 	}
 
 	if (hasMultipleMembers) {
 		const diverse = getMostDiverseMember(analytics, members);
-		questions.push({
-			type: "choice",
-			text: "Who looks like the most diverse listener in the party?",
-			options: buildMemberOptions(diverse, members),
-			correct: 0,
-			points: 10,
-			song: topSong ?? undefined,
-		});
-
-		const aligned = getMostAlignedMember(analytics, members);
-		questions.push({
-			type: "choice",
-			text: "Which member seems most aligned with the rest of the party?",
-			options: buildMemberOptions(aligned, members),
-			correct: 0,
-			points: 10,
-			song: topSong ?? undefined,
-		});
-
-		questions.push({
-			type: "choice",
-			text: "Who would you ask for a recommendation based on the party taste?",
-			options: buildMemberOptions(aligned, members),
-			correct: 0,
-			points: 10,
-			song: topSong ?? undefined,
-		});
+		if (diverse) {
+			const options = buildMemberOptions(diverse, members);
+			if (options) {
+				questions.push({
+					key: "social:diverse",
+					subjectKey: `member:${diverse.userId}`,
+					question: {
+						type: "choice",
+						text: "Who looks like the most diverse listener in the party?",
+						options,
+						correct: 0,
+						points: 10,
+						song: topSong ?? undefined,
+					},
+				});
+			}
+		}
 	}
 
 	const topTracks = getTopClusterTracks(analytics);
@@ -83,32 +81,43 @@ export async function buildSocialQuestion(
 				artistNames: randomTrack.artists?.map((artist) => artist.name),
 				albumName: randomTrack.albumName,
 			});
-			questions.push({
-				type: "choice",
-				text: `Who is most likely to have "${randomTrack.name}" in heavy rotation?`,
-				options: buildMemberOptions(topListener, members),
-				correct: 0,
-				points: 10,
-				song: randomTrackSong ?? topSong ?? undefined,
-			});
+			const options = buildMemberOptions(topListener, members);
+			if (options) {
+				questions.push({
+					key: `social:track-listener:${randomTrack.name}`,
+					subjectKey: `track:${randomTrack.name}`,
+					question: {
+						type: "choice",
+						text: `Who listens the most to "${randomTrack.name}"?`,
+						options,
+						correct: 0,
+						points: 10,
+						song: randomTrackSong ?? topSong ?? undefined,
+					},
+				});
+			}
 		}
 	}
 
-	if (members.length >= 3 && analytics?.pairwise?.length) {
-		const topPair = analytics.pairwise[0];
-		const memberA = members.find((m) => m.userId === topPair?.userIdA);
-		const memberB = members.find((m) => m.userId === topPair?.userIdB);
+	if (members.length >= 3 && analytics?.groupSummary?.mostAlignedPair) {
+		const topPair = analytics.groupSummary.mostAlignedPair;
+		const memberA = members.find((m) => m.userId === topPair.userIdA);
+		const memberB = members.find((m) => m.userId === topPair.userIdB);
 		if (memberA && memberB) {
 			const correctPair = `${memberA.name} & ${memberB.name}`;
 			const pairOptions = buildMemberPairOptions(members, correctPair);
 			if (pairOptions) {
 				questions.push({
-					type: "choice",
-					text: "Which two players would probably agree on the aux?",
-					options: pairOptions,
-					correct: 0,
-					points: 10,
-					song: topSong ?? undefined,
+					key: `social:pair:${memberA.userId}:${memberB.userId}`,
+					subjectKey: `pair:${[memberA.userId, memberB.userId].sort().join("|")}`,
+					question: {
+						type: "choice",
+						text: "Which two players share the most musical taste?",
+						options: pairOptions,
+						correct: 0,
+						points: 10,
+						song: topSong ?? undefined,
+					},
 				});
 			}
 		}
@@ -118,7 +127,7 @@ export async function buildSocialQuestion(
 		return null;
 	}
 
-	const question = questions[index % questions.length];
-	if (!question) throw new Error("Question not found");
+	const question = pickQuestionCandidate(questions, quizState.history, index);
+	if (!question) return null;
 	return buildQuestionWindow(question);
 }
diff --git a/dev-proxy/package.json b/dev-proxy/package.json
index cb16183..fc8dd79 100644
--- a/dev-proxy/package.json
+++ b/dev-proxy/package.json
@@ -3,6 +3,9 @@
 	"module": "index.ts",
 	"type": "module",
 	"private": true,
+	"scripts": {
+	  "dev": "bun run --watch index.ts"
+	},
 	"devDependencies": {
 		"@types/bun": "latest"
 	},
diff --git a/web/src/components/party/question.tsx b/web/src/components/party/question.tsx
index 446f6a9..d61e7f8 100644
--- a/web/src/components/party/question.tsx
+++ b/web/src/components/party/question.tsx
@@ -24,6 +24,10 @@ import { useSpotifyPlayer } from "#/hooks/use-spotify-player";
 import { useUser } from "#/hooks/user";
 import { client } from "#/lib/eden";
 
+type PartyQuestion = NonNullable<
+	NonNullable<ReturnType<typeof useParty>["party"]>["data"]["currentQuestion"]
+>;
+
 function formatTimeLeft(milliseconds: number) {
 	const clamped = Math.max(0, milliseconds);
 	const totalSeconds = Math.ceil(clamped / 1000);
@@ -34,6 +38,17 @@ function formatTimeLeft(milliseconds: number) {
 	return `${minutes}:${seconds}`;
 }
 
+function getQuestionAnnouncement(question: PartyQuestion) {
+	if (question.type === "numeric") {
+		return `${question.text}. Choose a number from ${question.range.min} to ${question.range.max}.`;
+	}
+
+	const options = question.options
+		.map((option, index) => `Option ${index + 1}: ${option}`)
+		.join(". ");
+	return `${question.text}. ${options}.`;
+}
+
 export function Question() {
 	const { party, members } = useParty();
 	const { user } = useUser();
@@ -48,6 +63,10 @@ export function Question() {
 			: null;
 	const { enabled: spotifyEnabled, setEnabled: setSpotifyEnabled } =
 		useSpotifyPlayer(spotifyTrackUri);
+	const questionStartTimestamp = question?.startTimestamp ?? null;
+	const questionAnnouncement = question
+		? getQuestionAnnouncement(question)
+		: null;
 
 	useEffect(() => {
 		const timer = window.setInterval(() => {
@@ -63,6 +82,26 @@ export function Question() {
 		setSelectedValue(question.type === "numeric" ? question.range.min : null);
 	}, [question]);
 
+	useEffect(() => {
+		if (
+			!questionAnnouncement ||
+			questionStartTimestamp == null ||
+			!("speechSynthesis" in window)
+		) {
+			return;
+		}
+
+		const utterance = new SpeechSynthesisUtterance(questionAnnouncement);
+		utterance.rate = 0.95;
+		utterance.pitch = 1;
+
+		window.speechSynthesis.cancel();
+		window.speechSynthesis.speak(utterance);
+
+		return () => {
+			window.speechSynthesis.cancel();
+		};
+	}, [questionAnnouncement, questionStartTimestamp]);
 	if (!question)
 		return (
 			<Section>