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The first draft of subway ads for this new location were rejected by the MBTA for touching on 'political issues or matters of public debate' and being potentially demeaning to a group of people (in this case, men). The Wing's eighth location opened in June 2019 in the Back Bay area of Boston, Massachusetts. Cregg of The West Wing, Lydia Deetz from Beetlejuice. The location also has a sound-proof screening room and film-themed phone booths names after Princess Leia from Star Wars, C.J. The West Hollywood location became the second location with an area for children. The same month, The Wing opened a seventh location on Santa Monica Boulevard in West Hollywood, California. In April 2019, The Wing opened its sixth location at the Fulton Market District in Chicago, Illinois. At the time, The Wing had raised a total of $117.5 million in funding since its founding. Among the investors were leaders of the Time's Up movement including Valerie Jarrett, Robbie Kaplan, Katie McGrath, Hilary Rosen, and Kerry Washington.

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In December 2018, the company closed a $75-million Series C led by Sequoia Capital, including investors Upfront Ventures, Airbnb, and others. The New York City Commission's investigation ended after the adoption of a formal policy allowing membership to people of any identity. The company says it only accepts about 8% of applicants вЂ“ those who it judges to be committed to its mission вЂ“ and that only 12 out of about 26,000 applicants were men. The company adopted a formal written policy that took effect in September of that year which accepts members regardless of gender identity. The Wing responded that prior to August 30, 2018, it had an unwritten policy of only accepting women (including transgender women) and gender non-binary people. Pietrangelo, a man described by TechCrunch as 'the dictionary definition of litigious', filed a lawsuit in August 2018, which claimed that The Wing's policy violated the District of Columbia's Human Right Act. Pietrangelo says an employee of The Wing told him his application would be automatically denied because he was a man. At that time, The Wing did not allow men even as guests of members (unlike two other New York City women's clubs noted by The New York Times вЂ“ Colony and Cosmopolitan), though it did hire some men such as plumbers and electricians. On March 1, 2018, the New York City Commission on Human Rights started a 'commission-initiated' investigation into how The Wing membership system operates.

At the end of 2018, The Wing announced it would offer on-site childcare services, The Little Wing, as part of the expansion of its SoHo location. The Washington, D.C., facility includes a booth dedicated to law professor Anita Hill while the San Francisco space has a conference room dedicated to psychology professor Christine Blasey Ford. During 2018, The Wing opened new spaces in the Dumbo neighborhood of Brooklyn (its third New York City location) in January in the Georgetown neighborhood of Washington, D.C., in April and in San Francisco, California, in October. The company raised an additional $32 million bringing their total investment to $42 million. In November 2017, The Wing completed a Series B round led by WeWork. They subsequently opened another branch in a loft in SoHo. The company raised $8 million from investors including Kleiner Perkins and BBG Ventures. The Wing closed its Series A funding round led by early-stage venture firm New Enterprise Associates in April 2017. The company raised $2.4 million from majority women seed investors including SoulCycle's Julie Rice and Elizabeth Cutler and Birchbox's Hayley Barna. In October 2016, Gelman and Kassan founded The Wing in New York City's Flatiron District, on the Ladies' Mile. When developing this idea, the two decided to focus on creating a space where women can feel safe and supported. When Gelman and Lauren Kassan began working together, they decided 'The Wing' was a more fitting name, since it would represent a 'wing' of the users' home away from their actual home. The first title for this not-yet-created space was Refresh. The initial idea for The Wing stemmed from Audrey Gelman's desire for a space to change and relax between business meetings as she lived in the New York City borough of Brooklyn, but worked in SoHo, Manhattan, and in Washington, D.C.

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