Added condition that early messages are shorter.

app/ai.py

@@ -3,14 +3,15 @@ from . import config, prompt, history
 
 _client = OpenAI(api_key=config.OPENAI_API_KEY)
 
-async def generate_reply() -> str:
+async def generate_reply(short: bool = False) -> str:
     msgs = history.build_messages(prompt.SYSTEM_PROMPT)
-    msgs.append({"role": "user", "content": prompt.USER_NUDGE})
+    # Use a tighter nudge for early small-talk
+    msgs.append({"role": "user", "content": prompt.EARLY_NUDGE if short else prompt.USER_NUDGE})
     resp = _client.chat.completions.create(
         model=config.OPENAI_MODEL,
         messages=msgs,
         temperature=0.8,
-        max_tokens=180,
+        max_tokens=80 if short else 180,
         presence_penalty=0.3,
         frequency_penalty=0.2,
     )

app/bot.py

@@ -34,12 +34,15 @@ async def run():
     async def debounced_reply(chat_id: int):
         await asyncio.sleep(config.DEBOUNCE_SEC)
         try:
-            reply = await ai.generate_reply()
+            # If it's the 1st or 2nd user message in the conversation, keep it extra short
+            user_count = history.count_role("user")
+            short_mode = user_count in (1, 2)
+            reply = await ai.generate_reply(short=short_mode)
         except Exception as e:
             print(f"OpenAI error: {e}")
-            reply = "sorry—mind saying that a bit slower? I get lost easy."
+            reply = "hey—sorry, got a bit mixed up. how are you doing?"
         history.append("assistant", reply)
-        await tg_helpers.send_with_catchup(client, chat_id, reply, ai.generate_reply)
+        await tg_helpers.send_with_catchup(client, chat_id, reply, lambda: ai.generate_reply(short=short_mode))
 
     @client.on(events.NewMessage(incoming=True))
     async def on_msg(event):

app/history.py

@@ -40,3 +40,9 @@ def build_messages(system_prompt: str):
         if r["role"] in ("user", "assistant"):
             msgs.append({"role": r["role"], "content": r["content"]})
     return msgs
+
+def count_role(role: str) -> int:
+    """Return how many messages of a given role are in the (pruned) history."""
+    recs = prune(load())
+    return sum(1 for r in recs if r.get("role") == role)
+

app/prompt.py

@@ -25,3 +25,8 @@ Output:
 """.strip()
 
 USER_NUDGE = "Please respond as Jon, following all the rules above. Keep it brief (1-4 short sentences)."
+
+EARLY_NUDGE = (
+    "Please respond as Jon with 1 short line (max 1–2 short sentences). "
+    "Keep it casual, a tiny typo is okay. A simple greeting + one friendly follow‑up is enough."
+)