“You go first.” “No, you go first.” Does it really matter who goes first? It depends, I suppose, on the context, circumstances, and personalities. At times, granting another the right-of-way or, in other situations, offering to take the lead, are gestures which reflect both thoughtfulness and grace. At other times, showing initiative and taking the first step may be the most effective way of facilitating an end to the gridlock that often disrupts and frustrates our interpersonal relationships.
As Elul begins, it may be worthwhile to consider the value of taking the first step and showing initiative. It is well known that our rabbis have sought to capture the special quality of the month of Elul, by noting its association to the pasuk, “אני לדודי ודודי לי”, “I am to my Beloved and my Beloved is to me.” On the surface, this formulation highlights the special relationship that exists between God and the Jewish people, reflecting an important feature of the month of Elul. As we make our way closer to the Aseres Yemei Teshuva, we remind ourselves of this special relationship, in an attempt to motivate and incentivize greater effort and attention in the weeks ahead.
The Sfas Emes suggests a much deeper message contained within this verse. On Rosh Hashanah, God makes His annual “appearance” to the world. On the day in which we coronate God as King of all kings, He emerges and appears, availing Himself to each and every one of us. By visiting the world in this way, Hashem demonstrates his commitment to mankind, as well as His love for the Jewish people. The date of his arrival is scheduled and the precise time is predetermined. On the first of the month of Tishrei, we experience the fulfillment of “ודודי לי”, my Beloved is to me. But rather than wait for Tishrei to begin in order for God to first reestablish our weakened connection, we deliberately choose to initiate that process; to preempt, as it were, God’s imminent arrival. Throughout the month of Elul, it is we who take the first steps towards repairing that which has been broken and restoring our fractured relationship. We do not wait for the moment of God’s revelation, for the remarkable display of “ודודי לי”. Rather, we inaugurate this glorious season by showing initiative; by demonstrating “אני לדודי”, first and foremost – I am to my Beloved. After taking the first step and after displaying our initiative – then “ודודי לי”, my Beloved is to me.
If demonstrating initiative within the realm of one’s relationship with God is indeed beneficial, it would seem as if much could also be gained by similarly applying ourselves in our interpersonal relationships. There is a common tendency that many of us have to procrastinate and postpone uncomfortable conversations that must take place. We continuously defer such encounters, in the hopes that they will be initiated by the other. This proclivity reflects a natural aversion to awkward moments and difficult discussions. While this tendency may be natural, it is appropriate for us to challenge ourselves and acknowledge that we can do better. It behooves us to recognize that to initiate a conversation which leaves one feeling vulnerable and exposed is, in and of itself, of great spiritual value, particularly during the season of repentance. Taking the first step towards reconciliation is often awkward, painful, and, at times, even humiliating. These feelings, while understandably uncomfortable, better enable us to achieve the proper state of mind during the days of awe.
In one month, we will all be paid a very special visit. Thankfully, our Visitor generously informs us of His itinerary prior to His arrival. Rather than show up unexpectedly, He provides us with an incredibly generous opportunity to prepare and ready ourselves for this extraordinary experience. The month of Elul is a gift with profound potential. But, like most gifts, it is up to the recipient to choose if and how it is to be properly utilized. The gift of Elul has been delivered. It is now for us to decide whether to take full advantage of this opportunity and initiate the process that is scheduled to begin.
“You go first.” “No, you go first.” Does it really matter who goes first? Sometimes actually, it does.
 Shir Hashirim 6:3
 Elul, 5661