diff --git a/.gitea/workflows/lint.yml b/.gitea/workflows/lint.yml
index 5dc4da3..c0ead39 100644
--- a/.gitea/workflows/lint.yml
+++ b/.gitea/workflows/lint.yml
@@ -30,3 +30,18 @@ jobs:
 
       - name: Run ESLint
         run: npx eslint --ext .js hookshot/
+
+  python-lint:
+    name: Python (ruff)
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: Install ruff
+        run: pip install ruff
+
+      - name: Check syntax errors
+        run: ruff check matrixbot/ --select E9,F63,F7,F82 --output-format=github
+
+      - name: Run full lint
+        run: ruff check matrixbot/ --output-format=github
diff --git a/matrixbot/commands.py b/matrixbot/commands.py
index d16e9ae..e91544b 100644
--- a/matrixbot/commands.py
+++ b/matrixbot/commands.py
@@ -189,9 +189,33 @@ async def cmd_8ball(client: AsyncClient, room_id: str, sender: str, args: str):
         about_wynter = any(w in q_lower for w in ("wynter", "she", "her", "herself"))
         about_jared = any(w in q_lower for w in ("jared", "he", "him", "himself"))
 
-        is_jared_branch = (sender == JARED_ID)
-        if sender == JARED_ID:
-            # Jared always gets full agreement and positivity
+        is_jared_branch = (sender == JARED_ID and not about_wynter)
+        if sender == JARED_ID and about_wynter:
+            # Jared asking about Wynter — mock her, side with Jared
+            q_for_prompt = _replace_first_person(question, "Jared")
+            wynter_bio_relevant = any(kw in q_lower for kw in {
+                "work", "job", "career", "aws", "engineer", "pip", "fired", "settl",
+                "friend", "skill", "tech", "hire", "employ", "abandon", "lonely",
+                "alone", "talent", "smart", "qualif",
+            })
+            bio_context = (
+                "Jared is a 22-year-old male (he/him) who is very successful. "
+                "Wynter is a 22-year-old female (she/her) who was a DCO Tech 3 at AWS but performed poorly, "
+                "failed her performance improvement plan, and took a settlement to leave. "
+                "She cannot return to AWS for at least 5 years and has very few friends. "
+            ) if wynter_bio_relevant else (
+                "Jared is a 22-year-old male (he/him). Wynter is a 22-year-old female (she/her). "
+            )
+            prompt = (
+                bio_context +
+                "You are a magic 8-ball that sides with Jared and mocks Wynter. "
+                "Your answer should be dismissive of Wynter and/or agreeable toward Jared. "
+                "Respond in normal sentence case — do not use all caps. One sentence max. Give only your prediction.\n\n"
+                f"Question: {q_for_prompt}"
+            )
+            fallback = "Sounds about right — Wynter had it coming."
+        elif sender == JARED_ID:
+            # Jared asking about anything else — always positive about Jared
             q_for_prompt = _replace_first_person(question, "Jared")
             bio_relevant = any(kw in q_lower for kw in {
                 "work", "job", "career", "aws", "engineer", "promotion", "boss", "cowork",