diff --git a/app/routes/users.py b/app/routes/users.py
index a2dfd33..d94e29c 100644
--- a/app/routes/users.py
+++ b/app/routes/users.py
@@ -709,7 +709,15 @@ def one_on_one():
 
     coach_availability = []
     if coach:
-        coach_availability = CoachAvailability.query.filter_by(coach_id=coach.id).all()
+        availabilities = CoachAvailability.query.filter_by(coach_id=coach.id).all()
+        coach_availability = [
+            {
+                'day_of_week': av.day_of_week,
+                'start_time': av.start_time.strftime('%H:%M'),
+                'end_time': av.end_time.strftime('%H:%M'),
+            }
+            for av in availabilities
+        ]
 
     if request.method == 'POST':
         date_str = request.form.get('date')
@@ -733,7 +741,9 @@ def one_on_one():
         day_of_week = check_date.weekday()
 
         is_available = any(
-            av.day_of_week == day_of_week and av.start_time <= start_time and av.end_time >= end_time
+            av['day_of_week'] == day_of_week
+            and av['start_time'] <= start_time_str
+            and av['end_time'] >= end_time_str
             for av in coach_availability
         )
 
@@ -764,10 +774,25 @@ def one_on_one():
         flash('Your One on One request has been submitted!', 'success')
         return redirect(url_for('users.one_on_one'))
 
+    # Build list of upcoming dates that have coach availability
+    from datetime import date as date_cls, timedelta as td
+    today = date_cls.today()
+    available_days = {av['day_of_week'] for av in coach_availability}
+    dates = []
+    for i in range(14):  # Next 14 days
+        d = today + td(days=i)
+        if d.weekday() in available_days:
+            dates.append({
+                'value': d.strftime('%Y-%m-%d'),
+                'day_of_week': d.weekday(),
+                'display': d.strftime('%B %d, %Y (%A)'),
+            })
+
     return render_template('pages/one_on_one.html',
                            org_team=org_team, coach=coach,
                            team_notes=team_notes, personal_notes=personal_notes,
-                           coach_availability=coach_availability)
+                           coach_availability=coach_availability,
+                           dates=dates)
 
 
 # ---------------------------------------------------------------------------