Ask AI: Should I ask out my best friends sister

It depends on the dynamics of your relationship with both your best friend and their sister. If you value your friendship with your best friend, it's important to talk to them first and see how they feel about the situation. If they are uncomfortable with the idea, it may be best to respect their wishes and not pursue their sister. However, if they are supportive, you can explore the possibility of asking their sister out. Remember to communicate openly and honestly with both your best friend and their sister, and be prepared to handle any challenges that may arise if you do decide to pursue a romantic relationship.