THE 14TH ANNUAL SHORTY AWARDS

The Shorty Awards honor the best of social media and digital. View this season's finalists!

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Bad Date Rebate

Finalist in Contest or Promotion, Financial Services

Objective

Venmo is North America’s leading peer-to-peer payment platform—making it easy to send, receive, and request money instantly. People can request money for anything…even bad dates. Now, for the first time, the brand is leaning into this organic behavior, transforming it into a bold, culture-driving moment that puts its users at the heart of the conversation.

 

Bad dates happen to everyone—but what if you could get reimbursed for the emotional damage? The Bad Date Rebate took a viral social trend—requesting money back after a terrible date from your bad date—and transformed it into a brand-backed movement.

 

On Valentine’s Day, we invited users to share their worst dating stories on the storytelling platform –  Instagram –  for a chance to get a rebate, tapping into the universal pain (and humor) of modern romance. The response was instant—stories flooded in, proving just how relatable dating disasters really are.

 

By turning heartbreak into a second chance, Venmo didn’t just acknowledge modern dating culture—it became part of it, stepping in (and paying up) when users needed it most.

 

Strategy

In today’s dating world, bad dates are more common than ever, often leaving hopeful romantics feeling discouraged. But a new trend has emerged—using Venmo to request money back after a disastrous date from your bad date (which got mixed reviews depending on who was on the receiving end).

The trend exploded into the mainstream when Love is Blind contestant Monica Davis used Venmo to request money from her cheating partner. The moment went viral, resonating with audiences as a cheeky stand against broken trust and sparking a larger conversation about accountability in modern dating.

Instead of shying away, we decided to take the movement even further—turning a viral behavior into a brand-backed activation. Enter Venmo’s Bad Date Rebate: a Valentine’s Day initiative designed to help the heartbroken bounce back. By reimbursing users for their worst dating experiences, Venmo didn’t just acknowledge the reality of modern romance—it gave people a fresh start, proving that even in love, a little financial justice goes a long way.

For the Bad Date Rebate, we transformed a viral cultural moment into a financial service offering that resonated with modern consumers. Partnering with:

 

Monica Davis (Love is Blind star, viral Venmo bad date request)

Stef Dag (comedian, Hot & Single podcast host)

Eric Sedeño (NYC socialite, hopeless romantic)

We brought a fun, authentic twist to financial services, amplifying the activation on Instagram through their comedic voices and loyal audiences.

 

The Rollout:

Tease: Venmo and each influencer kicked off with a countdown sticker on Instagram Stories, sparking curiosity and excitement ahead of Valentine’s Day.

Behind-the-Scenes Hype: Influencers filmed candid, real-time selfie videos from the set, maintaining authenticity and anticipation for the campaign launch.

Launch: A collaborative post featuring all three influencers and Venmo officially unveiled the Bad Date Rebate, inviting followers to share their worst date stories in exchange for a chance to win their money back. The response was overwhelming.

Engagement: On Valentine’s Day, the trio reacted to the funniest and most relatable stories, creating a viral push for more submissions.

In the Wild: Stef hit the streets of NYC, surprising fans with on-the-spot Bad Date Rebates for sharing their stories.

The Payout: A few days later, 210 bad date sufferers received $250 reimbursements from Venmo, encouraging them to keep trying in the world of love.

 

The Bad Date Rebate seamlessly connected financial services with real-life moments, turning dating mishaps into financial wins and proving that even heartbreak deserves a refund.

 

Results

Media

Video for Bad Date Rebate

Entrant Company / Organization Name

72andSunny, Venmo | PayPal

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