2021 Virtual Cupid’s Undie Run Highlights

The best way to spend a pandemic is pantless. 2020/21 was a bad chapter in a dystopian novel, but our Cupid’s fam came together despite these trying times. We fundraised [...]

The best way to spend a pandemic is pantless.

2020/21 was a bad chapter in a dystopian novel, but our Cupid’s fam came together despite these trying times. We fundraised our pants off, $900K to be specific! We couldn’t have done it without all of our amazing teams, participants, donors, event directors, board members, and staff—phew, that’s a mouthful! You get the point. 

We continued to lead with love this year as we completed our first virtual Cupid’s Undie Run. Cherubs from across the nation completed their mile-ish undie run in any way they pleased and showed the world why Cupid’s is a #MileThatMatters, pandemic or not. In such a strange year, we wanted to encourage creativity, that’s why we gave participants the reins to decide how they wanted to complete a #MileThatMatters. And boy, did they show up. Don’t believe us? Check out these recap videos and see for yourself!


Since we couldn’t stop laughing, crying, and ‘awwing’ as we watched you complete your miles, it only seemed fit to award our favorites. Here are the winners of our three categories; Funniest Mile, Most Heartfelt Mile, and Best Cupid’s Spirit.

Funniest Mile: Robert Byers


Entry for “Best Cupid’s Spirit” #cupidsundierun #imwithcupid #milethatmatters #EndNF

♬ original sound – Cupid’s Charity

Most Heartfelt Mile: Erica O’Grady


Submission for “Most Heartfelt Mile” #imwithcupid #cupidsundierun #EndNF #neurofibromatosis #nf #milethatmatters #itakemypantsoffforcharity

♬ original sound – Cupid’s Charity


Best Cupid’s Spirit: Brad Polzar 


Submission for “Best Cupid’s Spirit” #cupidsundierun #imwithcupid #EndNF #milethatmatters #nonprofit #itakemypantsoffforcharity

♬ original sound – Cupid’s Charity

Because we went virtual this season, we were able to host a LIVE nationwide event, something we’d never dipped our toes into before! As a community, we gathered in our respective cities in our bubbles of friends and family to drop our pants and tune in for the show on February 13th, 2021. 

Through the screen, we mixed cocktails with professional mixologist Robby Nelson, we were also joined by Bravo TV’s Top Chef All Star Nini Nguyen, former Superbowl champ Omar Bolden, and more! It most definitely wasn’t your average Zoom call. Our ongoing game of “drink whenever you hear the word unprecedented” might have left us with a bit of a headache the next morning, but it’s all a part of the Cupid’s Undie Run experience! After all of our hard work fundraising, everyone deserved to celebrate with a cocktail . . . or two! Plus, we successfully tossed a pair of undies across America and to our pals Down Under! Check out the video below to see how we slung our skivvies from state to state.

Thursdays became our favorite days

Leading into our Virtual Cupid’s Undie Run, Thursday evenings became somewhat of a ritual for Cupid’s as we gathered for several Thirsty Thursday Happy Hours. We were joined by a superb team of celebrities to help us celebrate. 

For starters, Robby Nelson of AMASS Botanics led us through a mixology class, not once but twice, so that we were fully equipped with cocktails to last us throughout quarantine. The lovely Bravo TV’s Top Chef All Star Nini Nguyen, taught us step-by-step how to make dumplings from scratch, all while sipping a nearby cocktail. Rapper and musician Kelley James made music right before our eyes. If you typed it into the chat, Kelley would surely incorporate it into a song! To finish things off, former Superbowl champ Omar Bolden led an at-home workout where he turned your cocktail into a weight so we could burn a few extra calories. 

Thursday Thursdays began as a way to engage our participants and encourage others to join, but they quickly became our favorite hour of the week. Getting to see familiar faces while learning new skills made for a nightcap we couldn’t forget. 

Looking forward to Cupid’s Undie Run 2022

We’re making plans to get back to hosting Cupid’s Undie Run in person all across the country in February 2022 and we can’t wait to see you there. Registration is open now if you’re ready to start planning your way out of the Covid cave you’ve been living in. See you soon, cherubs!

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