diff --git a/matrixbot/commands.py b/matrixbot/commands.py
index 859dfa9..cb31e50 100644
--- a/matrixbot/commands.py
+++ b/matrixbot/commands.py
@@ -1647,11 +1647,15 @@ def record_wyr_vote(event_id: str, sender: str, key: str) -> None:
 
 async def _generate_wyr() -> dict | None:
     system_msg = (
-        "You are a game host generating Would You Rather questions. "
+        "You are a game host generating Would You Rather questions for a group of adult friends. "
         "Always respond with ONLY a JSON object — no markdown fences, no explanation. "
-        'Format: {"question": "Would you rather...", "option_a": "short option", "option_b": "short option"}'
+        'Format: {"question": "Would you rather...", "option_a": "short option", "option_b": "short option"}\n'
+        "Make the dilemma genuinely difficult — both options should have real downsides so it's actually a hard choice. "
+        "Be creative and edgy: embarrassing scenarios, weird superpowers, social nightmares, gross but survivable situations, "
+        "impossible tradeoffs. Avoid boring safe options like 'dance with dolphins' or 'sing karaoke'. "
+        "Keep each option under 10 words."
     )
-    user_msg = "Generate a fun, creative Would You Rather question. Keep each option under 10 words."
+    user_msg = "Generate a spicy, genuinely difficult Would You Rather question."
     try:
         timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
@@ -1774,9 +1778,16 @@ async def _generate_riddle() -> dict | None:
     ) if _riddle_recent else ""
     system_msg = (
         "You are a riddle generator. Always respond with ONLY a JSON object — no markdown fences, no explanation. "
-        'Format: {"riddle": "the riddle text", "answer": "short answer"}'
+        'Format: {"riddle": "the riddle text", "answer": "short answer"}\n'
+        "Rules for a good riddle:\n"
+        "- The answer must be a specific, unambiguous noun (1-3 words). Avoid abstract answers.\n"
+        "- The riddle must describe the answer through metaphor or wordplay — NOT by literally describing it.\n"
+        "- Do NOT include the answer word anywhere in the riddle text.\n"
+        "- Do NOT end the riddle with 'what am I?' or 'what could it possibly mean?' — the riddle should stand alone.\n"
+        "- The clues must logically point to ONE specific answer. Test it: would most people agree this answer is correct?\n"
+        "- Avoid riddles about riddles, shadows, or abstract concepts. Prefer concrete things: candle, mirror, clock, river, echo, stamp, etc."
     )
-    user_msg = f"Generate a clever, original riddle. The answer should be 1-4 words.{avoid_clause}"
+    user_msg = f"Generate a clever, original riddle with a clear unambiguous answer.{avoid_clause}"
     try:
         timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
@@ -1856,14 +1867,26 @@ async def cmd_riddle(client: AsyncClient, room_id: str, sender: str, args: str):
     _RIDDLE_ACTIVE[room_id]["task"] = task
 
 
+def _riddle_matches(answer: str, body: str) -> bool:
+    """Fuzzy match: strip articles, allow the core word to appear in the guess or vice versa."""
+    def _normalize(s: str) -> str:
+        s = s.strip().lower()
+        for art in ("a ", "an ", "the "):
+            if s.startswith(art):
+                s = s[len(art):]
+        return s.strip()
+
+    ans = _normalize(answer)
+    guess = _normalize(body)
+    return ans == guess or ans in guess or guess in ans
+
+
 async def check_riddle_answer(client: AsyncClient, room_id: str, sender: str, body: str) -> bool:
     """Check if a room message answers the active riddle. Returns True if correct."""
     if room_id not in _RIDDLE_ACTIVE:
         return False
     game = _RIDDLE_ACTIVE[room_id]
-    answer_lower = game["answer"].lower()
-    body_lower = body.strip().lower()
-    if answer_lower in body_lower:
+    if _riddle_matches(game["answer"], body.strip()):
         task = game.get("task")
         if task:
             task.cancel()