Worlds Behind Words 9: Stonewall Pride Flag, Federal DEI Rollbacks, and Body Image Pressure

Author(s): Scott Douglas Jacobsen

Publication (Outlet/Website): The Good Men Project

Publication Date (yyyy/mm/dd): 2026/03/08

William Dempsey, LICSW, is a Boston-based clinical social worker and LGBTQ+ mental-health advocate. He founded Heads Held High Counselling, a virtual, gender-affirming group practice serving Massachusetts and Illinois, where he and his team support clients navigating anxiety, depression, trauma, ADHD, and gender dysphoria. Clinically, Dempsey integrates EMDR, CBT, IFS, and expressive modalities, with a focus on accessible, equity-minded care. Beyond the clinic, he serves on the board of Drag Story Hour, helping expand inclusive literacy programming and resisting censorship pressures. His public scholarship and media appearances foreground compassionate, evidence-based practice and the lived realities of queer communities across North America.

Scott Douglas Jacobsen and Will Dempsey examine representation across institutions, culture, and health. They discuss the National Park Service’s decision to stop the Pride flag at Stonewall, the February 12, 2026, re-raising, and proposed federal protections as a test of public memory and morale. Dempsey frames removals as symbolic erasure amid political tension, linking them to disputes over historical exhibits and broader “anti-woke” filtering. They also address advocacy triage, with trans healthcare prioritized over language policing. The conversation turns to Eating Disorders Awareness Month, noting elevated body dysmorphia and disordered eating among gay men and transfeminine clients.

Scott Douglas Jacobsen: This is a win. The National Park Service stopped flying a rainbow Pride flag at the Stonewall National Monument in Manhattan in early February 2026, citing federal flag policy. Stonewall marks the site of the 1969 uprising that catalyzed the modern LGBTQ+ rights movement in the United States, so the flag’s presence there is historically contextual, not decorative.

New York officials and activists re-raised the Pride flag at the site on February 12, 2026. Following that, Senate Minority Leader Chuck Schumer announced plans to introduce legislation to protect the ability to fly the Pride flag at Stonewall and, more broadly, on federal property. Representatives, including Dan Goldman and Senator Kirsten Gillibrand, voiced support.

You have likely heard more about this than I have, given that I am in Ukraine. What are your thoughts? When symbols are appropriately placed for specific identity groups in the United States who value them, while most people may not care about monuments, many do—what does this mean to them? How does it affect community morale?

Will Dempsey: Representation matters. In a political climate marked by tension between LGBTQ+ communities and the current administration, the removal of the Pride flag at Stonewall was widely interpreted as symbolic erasure rather than routine policy enforcement.

This followed controversy in Philadelphia, where elements of a National Park Service exhibit at the President’s House site, detailing enslaved people held by George Washington, were removed after an executive order addressing federal historical interpretation. A federal judge later ordered the exhibit restored, and the panels were reinstalled after legal and public pressure.

The Pride flag being re-raised at Stonewall—whether through official reconsideration or civic protest—carries symbolic weight. Stonewall’s history centers on resistance to marginalization. The act of restoring the flag signals that many people, inside and outside the LGBTQ+ community, continue to support inclusion and public recognition. It also underscores that those in power do not necessarily reflect the broader national consensus.

Nations have complicated histories because much of human history fails to meet contemporary universal ethical standards, such as human rights and humanitarian law. Commemoration is not about sanitizing history; it is about marking moral progress and safeguarding hard-won gains.

The debate reflects differing interpretations of what monuments represent. Some do not see Stonewall as a positive symbol of civic inclusion. That position differs significantly from debates over Confederate monuments, yet both controversies hinge on how national identity and historical memory are publicly expressed.

Jacobsen: Some people might perceive these issues as similar, even though the historical contexts and communities involved are very different. At the federal level, there has been a push within the United States government to purge or block references to content officials categorize as “woke.” Some examples, highlighted in media commentary, included automated removals of terms such as “gay,” which reportedly led to references to historical events like the Enola Gay being flagged because of keyword filtering.

We are now seeing another round of this. Reports from outlets including NBC News, Politico, and the Associated Press indicated that the Pentagon flagged approximately 26,000 images and posts for deletion as part of a broader effort to remove diversity, equity, and inclusion content from Department of Defence platforms.

What is the messaging here? How is this being received in community commentary, particularly regarding the Pentagon?

Dempsey: Transparently, much of the community’s online discourse is currently focused elsewhere, including attention on the Epstein files. Some view actions like this as a distraction from other issues they consider more urgent.

That said, there is a longer historical lens through which this is interpreted. Many in the LGBTQ+ community have long felt that federal institutions have attempted to marginalize or erase them—from the Reagan administration’s response to the AIDS epidemic to various policy debates since. Actions perceived as removing language or representation can be read within that broader historical narrative.

While it may be recognized as a setback—similar in symbolic terms to the Stonewall flag issue—there is also a pragmatic understanding that not every setback can receive equal energy. Within the community, trans rights and access to trans healthcare are often seen as more immediate priorities than language filtering controversies.

There is a long history of triaging advocacy efforts: recognizing that setbacks will occur and deciding strategically where to invest energy.

Jacobsen: February is recognized in the United States as National Eating Disorders Awareness Month. There has been increasing advocacy highlighting the struggles of gay men who may experience bulimia, body image pressures, or body dysmorphia. How effective are awareness months like this? And how are they incorporated into social workers’ regular practice?

Dempsey: Awareness months are not always deeply integrated into day-to-day clinical practice, which speaks to both their limits and their function. They tend to raise visibility rather than structurally reshape care.

In our office, we do see elevated rates of body dysmorphia and disordered eating among gay men, and particularly among trans women. As our practice has grown and we have gathered more internal data over the past year or two, we have observed increased rates of disordered eating among transfeminine clients.

These issues are real and clinically significant. Awareness campaigns can help normalize conversations and reduce stigma, but sustained interventions depend on ongoing access to competent care rather than a designated month of recognition.

Awareness months create opportunities to open conversations. They remind us to check in with one another at a communal level and, professionally, with clients about what they may be experiencing.

Body image pressures have been apparent in the gay community for a long time. There is a historical context tied to the HIV/AIDS epidemic and the way physical appearance became heavily scrutinized within parts of the gay male community. That history continues to shape contemporary body standards.

As more transfeminine people come out, transition, and gain broader—though still incomplete—social acceptance, they are increasingly subject to the same societal expectations placed on women’s bodies. Even incremental shifts in visibility can intensify exposure to those norms. That may help explain why we are continuing to see parallels between transfeminine individuals and patterns of body dysmorphia, similar to what gay men have experienced for decades.

Jacobsen: Let me shift the angle slightly. Goldman Sachs recently dropped race, gender, and LGBTQ+ criteria from its board diversity requirements. At the same time, the 2026 Film Independent Spirit Awards highlighted achievements such as Eva Victor winning Best Screenplay and Arian Moayed receiving recognition in acting categories.

In one context, the corporate world, formal diversity criteria are being removed from board evaluations. In another, the arts, representation emerges through talent, achievement, and awards. In corporate governance, what happens when intentional representation criteria are removed? In the arts, when individuals from historically underrepresented communities win major awards, what effect does that have on long-term representation and community visibility?

Dempsey: If I understand correctly, the question centers on representation in different contexts—intentional diversity initiatives versus achievement-based recognition.

Debates around diversity, equity, and inclusion often frame this as intentional representation at the table versus “earning” a place without structured consideration. In reality, there has to be a balance.

Without intentional efforts to diversify leadership spaces, historical patterns tend to reproduce themselves because those patterns are rooted in longstanding privilege and access disparities. At the same time, individuals who hold leadership positions or receive awards still earn them through competence and effort. Representation does not negate merit.

Critics of diversity initiatives worry that positions are handed out. That framing overlooks systemic barriers that have historically limited access. Ensuring access and opportunity does not mean lowering standards.

In short, intentional inclusion and earned achievement are not mutually exclusive. They can, and arguably should, operate together to create fairer and more representative institutions over time.

There needs to be safeguards to ensure that whoever is setting the proverbial table is intentional in how people are selected—due diligence matters. Leadership should actively ensure that diverse communities are represented and that their voices are heard, while avoiding the practice of offering a seat solely for symbolic purposes. There is a delicate balance between intentional representation and maintaining merit-based standards.

As conversations around diversity, equity, and inclusion continue to evolve, this tension remains central, particularly in spaces where diversity has historically been limited. Once political tensions have settled, there could be broader, thoughtful societal discussions about how to approach this responsibly and sustainably.

Jacobsen: I can feel us both losing energy, so we will call it a night. 

Dempsey: Sounds good. Take care of yourself. I am genuinely glad that you are alive and well. Stay vigilant. Sleep well.

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