OPINION & ORDER Before the Court are three motions: (1) Plaintiff’s motion for leave to amend his complaint; (2) Plaintiff’s motion to compel Defendant to produce documents and answer interrogatories; and (3) Defendant’s motion to compel Plaintiff to produce documents.BACKGROUNDPlaintiff, initially proceeding pro se, filed his complaint on December 12, 2017. ECF No. 1. He alleges that he is the registered owner of the “DEFEND BROOKLYN” trademark. Id.,
12-14. Defendant infringed this trademark, Plaintiff claims, by selling clothing items bearing the mark, “DEFEND PARIS,” with an allegedly similar design as “DEFEND BROOKLYN.” Id. at 16.Discovery closed on September 28, 2018. ECF No. 16. Nevertheless, on October 22, Plaintiff requested leave to seek additional documents and depositions. ECF No. 25. The Court granted Plaintiff’s request and extended the discovery deadline until January 21, 2019. ECF No. 26.Despite the Court’s extension, it does not appear that the parties engaged in any additional discovery during the following months. Then, on December 20, Defendant asserted that Plaintiff had not responded to Defendant’s July 31 discovery requests. ECF No. 27. The Court held a conference on January 4, where an attorney appeared on behalf of Plaintiff. ECF No. 28. By January 11, the Court directed Plaintiff’s counsel to file a notice of appearance; to serve Plaintiff’s document production on Defendant; and to identify in writing any claimed deficiencies in Defendant’s production. The Court also extended the discovery deadline until February 21, 2019, cautioning that no further extensions would be granted. ECF No. 29.On January 17, Defendant stated that Plaintiff had “failed to do any of the tasks that the Court directed at the [January 4] conference.” ECF No. 33. Following another conference on January 30, the Court once again extended the discovery deadline, this time until April 1, 2019. ECF No. 36.On March 26 — three business days before the close of discovery — Plaintiff requested that the Court (1) compel Defendant to produce additional documents; (2) grant Plaintiff leave to file an amended complaint; and (3) extend the deadline (for a fourth time) to complete discovery. ECF No. 37. Defendant opposed Plaintiff’s request and argued that, in addition, Plaintiff had failed to produce responsive documents. ECF No. 38. The Court issued an order regarding the parties’ disputes on April 4. Given that Plaintiff had only recently obtained counsel, the Court granted a final extension of the discovery deadline until May 15. In addition, because the parties had not completed the meet-and-confer process, the Court directed the parties to file any discovery letters by April 12 and to attend a discovery conference on April 16. The Court also set a briefing schedule for Plaintiff’s request for leave to file an amended complaint. ECF No. 39.Despite not filing any discovery letters by the April 12 deadline, both parties raised discovery issues during the April 16 conference. The Court ordered that any motion to compel must be filed by April 22 and that any opposition must be filed by April 24. Both parties subsequently filed a motion to compel, but only Defendant filed a letter in opposition. The parties’ motions are now ripe for review.DISCUSSIONI. Plaintiff’s Motion to Amend his ComplaintPlaintiff requests leave to join five additional defendants: (1) Defend Paris, a French corporation and the alleged alter ego of Defendant New Moda; (2) Sweet Charms, LLC, the manufacturer and distributor for Defend Paris; (3) Omar Ohebsian, an alleged co-owner of New Moda; (4) Mark Mechaly, another alleged co-owner of New Moda; and (5) Eran Haroni, an alleged co-owner of both New Moda and Defend Paris (collectively, the “Proposed Defendants.”). ECF No. 43, at 1; ECF No. 43-1, Proposed Amended Complaint (“PAC”),
