In today's unscripted live coaching episode, I coach Jennifer about relationships, and more specifically, how it feels to be happily single in middle age after a lifetime of being in serious romantic relationships. Is it better to push yourself back into dating and gain the safety and companionship of a partner—at the risk of losing yourself? Or stay single and live a creatively fulfilling life, at the cost of feeling alone and sexually unfulfilled? Then I coach Natalie about situations in which your truth is going to hurt or disappoint someone else—and how to be more trusting and open with our loved ones in a way that still feels safe and true to yourself.