If you are in a leap of faith moment, you will know it. Even while the moment is happening you can feel the looming regret from not jumping. Especially when your moment features that gorgeous girl you can't stop thinking about and deep down you think she likes you too. You can see that this moment is the fork in your road of life. You know which road you want to take, but you can't find the courage to drive down the rocky road to happiness.
In this moment many thoughts pour through your head. You worry about saving face. You worry about getting hurt. You worry about what people will say. These thoughts are not your friend. They are the carriers of regret; the inner demons of your future self.
Through my limited personal experience I have learnt there is but one rule in a leap of faith situation. You need not consider a single outcome. Don't think about how awkward situations may follow. Think about the one thing you want and the first step required to achieve it: