May is a curious month for communications teams. Within roughly 72 hours, brands can find themselves navigating a beloved fan holiday, the most-watched fashion event on the planet, and a cultural celebration that demands real sensitivity. Each one rewards a completely different approach, and the brands that win in May are the ones that recognize this rather than treating every holiday as another excuse for a themed graphic.
Below is a practical, phase-by-phase PR playbook for all three, built around the same three-stage framework: lead-up, day-of, and post-holiday retention. Because here is the thing most brands miss: the goal is not the spike. The goal is what the spike turns into.
Star Wars Day (May 4)
“May the Fourth be with you” has evolved from a fan pun into a genuine commercial moment, with Disney, LEGO, retailers, and even financial services brands building campaigns around it. Because Star Wars fandom is multigenerational and emotionally charged, this is a holiday where authenticity beats polish every time.
Lead-Up (T-minus 3 to 4 weeks)
Start by auditing your licensing situation. If you have any official Star Wars partnership, even a minor one, this is the time to confirm asset rights, approval timelines, and what language Lucasfilm will and will not allow. If you do not have a license, your strategy shifts entirely toward fandom-adjacent content: nods, references, and culture rather than logos and characters.
Two weeks out, begin teasing. Tease cryptically. Star Wars fans love decoding things, so a Holocron-style countdown, a Morse-code Aurebesh hint, or a redacted product reveal performs better than a straightforward announcement. Brief your customer service team on common questions, expected order volume, and on-brand voice for the day, because nothing punctures the magic faster than a robotic chatbot reply on May 4th.
This is also the window to lock in creator partnerships. The Star Wars creator ecosystem is deep and tiered, and micro-creators with 20k to 100k followers often deliver better engagement than celebrity tie-ins, because their audiences trust them as fans first.
Day-Of (May 4)
Your social team should be live and reactive, not scheduled and silent. The biggest mistake brands make on May 4th is queuing up one branded post at 9am and walking away. Successful brands act like they are at the party: replying to fan content, jumping into trending conversations, and rewarding clever comments with custom replies.
Drop something with real value. A limited edition product, an exclusive bundle, a free download, a charity tie-in with Star Wars: Force for Change. The day rewards generosity. Brands that try to ride the hashtag without offering anything tangible get called out quickly.
If you are running paid media, dayparting matters. Engagement spikes between 7am and 11am as people post their morning “May the Fourth” content, and again in the early evening as fans share rewatches and family activities.
Post-Holiday Retention
Here is where most brands drop the ball. They post on May 4th, see the engagement, and move on. The retention play happens in the seven to ten days after.
Send a follow-up email to anyone who engaged, purchased, or signed up that day, but do not pitch them more product. Pitch them more story. Behind-the-scenes content, the team’s favorite Star Wars moments, a recap of fan submissions you loved. You are converting a transaction into a relationship.
Build a UGC compilation by May 7th and credit every fan you feature. Tag them, message them, send them something small. These are the people who become repeat customers and word-of-mouth amplifiers next year. Add anyone who opted in to a “fandom” segment in your CRM, and keep that audience warm with relevant content year-round, not just next May.
"Star Wars fans don't want to be marketed to, they want to be invited in. The brands that win on May 4th show up as fellow fans, not as advertisers wearing costumes, and the ROI doesn't show up in that day's revenue. It shows up in who's still talking about you six months later."
Met Gala Monday (First Monday in May)
The Met Gala is the rare cultural event where the entire internet is paying attention to the same thing at the same time, and the conversation moves at a speed most brand teams are not built for. The PR opportunity here is not really about being at the gala. It is about being part of the cultural commentary surrounding it.
Lead-Up (T-minus 4 to 6 weeks)
The theme drops months in advance, and your team should already know it cold. Read the curatorial notes from the Met’s Costume Institute, not just the press release. Understand what the dress code actually means versus what people will assume it means. The brands that nail Met Gala commentary are the ones whose teams can explain why a look works, not just whether it does.
Build a war room plan. Identify who on your team will be live during red carpet hours, who is approving copy in real time, and what your escalation path looks like if a conversation goes sideways. If your brand has any tangential relevance to fashion, beauty, design, or culture, you should have pre-approved response templates ready for likely scenarios: a viral look, a controversial look, an absent celebrity, a surprise guest.
For brands actually involved (designers, jewelers, beauty sponsors, hotel partners), the lead-up is a press push: exclusive sneak peeks to a small handful of trusted outlets, behind-the-scenes content for owned channels, and tightly coordinated talent comms. Hold something back for day-of. Do not give everything to the previews.
Day-Of (Met Monday)
Carpet coverage typically runs from late afternoon Eastern time into the evening. Your team should be fully staffed during that window, with social, PR, and creative working in the same room or the same Slack channel.
The play is real-time commentary, not real-time selling. Brands that try to slap a product link onto a celebrity look look transparently opportunistic. Brands that offer genuine fashion analysis, witty observations, or thematic connections get reshared. There is a meaningful difference between “Zendaya’s look reminds us of our spring collection” (bad) and “Zendaya’s silhouette is a direct reference to a 1954 Dior gown, here is why that matters for the theme” (good).
If your brand has no organic fashion connection, consider sitting this one out at the brand level and letting your executives or relevant team members participate as individuals on LinkedIn or X with informed takes. Forced participation is worse than non-participation.
Post-Holiday Retention
The Met Gala generates roughly 48 hours of intense conversation, then a long tail of think-pieces, best-dressed lists, and trend reports that runs for two to three weeks. This long tail is where the retention work happens.
By Wednesday, publish your own recap content. A trend report tying the gala back to your industry, a “looks we loved” feature, a piece on the underdog designers who dressed someone unexpected. Long-form content here gets shared in industry newsletters and reaches an audience your day-of social posts never will.
For brands with email lists, segment anyone who engaged with your gala content into a “culture-forward” audience and adjust their content cadence accordingly. These are people who care about cultural moments, not just product drops, and they respond to a different content mix.
Finally, debrief internally within the same week. What worked, what did not, who responded fastest, where the bottlenecks were. The Met Gala is a stress test for your real-time capabilities, and the lessons translate to every other live cultural moment your brand will encounter the rest of the year.
"The Met Gala is a stress test for your real-time muscles. The brands that get reshared aren't the ones selling against the carpet, they're the ones saying something genuinely interesting about it. Taste travels further than promotion, and on Met Monday it travels at the speed of a group chat."
Cinco de Mayo (May 5)
This is the holiday where the most important PR strategy is often deciding not to participate, or participating in a way that is meaningfully different from what most brands have historically done. Cinco de Mayo commemorates the Mexican army’s victory at the Battle of Puebla in 1862, and while it has become a broader celebration of Mexican-American culture in the United States, it has also been heavily commercialized in ways that frustrate the communities the holiday actually belongs to.
Lead-Up (T-minus 4 to 6 weeks)
Start with an honest internal conversation. Does your brand have a genuine connection to Mexican culture, Mexican-American communities, or Mexican products and ingredients? If the answer is no, the most credible PR strategy is to either skip it or participate as a respectful guest rather than a host.
If you are participating, the lead-up is about partnership, not production. Identify Mexican-owned businesses, Mexican-American creators, and community organizations you can work with in ways that are paid, credited, and creatively led by them. This is not a sponsorship logo on someone else’s content. This is genuine collaboration where the cultural authority sits with people who actually have it.
Brief your team thoroughly. Make sure everyone touching the campaign understands the difference between Cinco de Mayo and Mexican Independence Day (September 16), can pronounce the names of any partners or products correctly, and knows which visual and verbal references are clichéd or stereotypical. The list of things to avoid is well-documented and not subtle: sombreros as decoration, fake mustaches, “Cinco de Drinko” puns, mariachi imagery used without context, anything that flattens a culture into a costume.
Day-Of (May 5)
If you have built a real partnership, the day-of execution should largely belong to your partners. Amplify their content, drive traffic to their businesses, share their stories. Your brand’s voice should be in service of theirs, not on top of theirs.
For food, beverage, and retail brands with authentic Mexican products or heritage, this is a day for storytelling. The history of a recipe, the supplier in Oaxaca, the family that has been making mezcal for four generations. People are paying attention on May 5th, and substantive content about Mexican craft, food, music, and history performs well precisely because so much competing content is shallow.
Do not push promotional discounts that frame the day as a party trope. “Margarita Monday” specials, taco bundles tied to clichéd imagery, and similar campaigns generate short-term sales and long-term brand damage with consumers who increasingly notice the difference.
Post-Holiday Retention
The single most important post-holiday move for Cinco de Mayo is to not disappear from these communities on May 6th. Brands that show up once a year and vanish reinforce the exact criticism that the holiday is exploited rather than celebrated.
Continue the partnerships you started. Feature your collaborators in May, June, and beyond. If you launched a product with a Mexican-American creator, keep selling and promoting it past the holiday window. If you donated to a community organization, share the impact in Q3, not just on May 5th.
Update your CRM with what you learned. Customers who engaged authentically with substantive content are different from customers who came for a discount, and they should be in different segments with different messaging strategies. The first group is a long-term retention opportunity. The second group will leave the moment a competitor offers a deeper discount.
For brands that decided not to participate this year, document why, and revisit the decision next year with the question of whether you have built the relationships and earned the standing to participate meaningfully in 2027.
"Cinco de Mayo isn't won on May 5th. It's won on May 6th, June 6th, and the following May, when communities can see whether the relationship was real or rented. The most strategic move a brand can make here is often to participate less, but to participate honestly, and to keep showing up after the hashtag stops trending."
A Final Thought on May
These three holidays, falling within roughly 24 hours of each other in some years, are a useful diagnostic for any communications team. Star Wars Day rewards fandom and generosity. The Met Gala rewards speed, taste, and cultural fluency. Cinco de Mayo rewards humility, partnership, and the discipline to play the long game.
Brands that do well in May are not the ones with the biggest budgets. They are the ones who understand that each holiday is asking them a different question, and who answer the question that was actually asked. The retention payoff comes weeks and months later, in the audiences you build, the partnerships you sustain, and the trust you earn by not treating every cultural moment like the same opportunity wearing different costumes.
