Cupid’s Undie Run – a More Cowbell Kind of Event

Imagine running around in your underpants on Valentine’s Day weekend… Now imagine doing it with hundreds of other people. In public. Would you do that? And before you yell, “Heck, NO!“…would you do it for a wonderful cause?

Our own posse member, Phil Holtberg, would. I’d venture to say he’d have run in his birthday suit if it was for a charity he believes in. He’s a giver like that.

Phil is participating in Cupid’s Undie Run NYC on February 13th and he’s hoping for some help from his pals here at More Cowbell.  Read on for all the fun deets!

When I asked him “why this run,” he said:

To give back. To do something good for those in need. I try to pick events each year that are athletic based with a charity cause attached to them.

Seems like each year now as I am getting older I am getting a bit crazier and put my body through hell more and more. The beatings are worth it though as I have raised thousands of dollars during these events, and I am truly humbled and thankful for everyone’s support.

It’s very gratifying to cross that finish line knowing I helped out if even in my own small way. All bumped, scraped, and bruised. Pain never felt so good.

Phil’s fundraising efforts so far:

Warrior Dash in 2013 for the St Jude’s Children’s Research Hospital


Warrior-Dash-2013_1 Warrior-Dash-2013_3

Tough Mudder in 2014 for the Wounded Warrior Foundation

Tough Mudder 1 Tough Mudder 3Tough Mudder 2

Urban Mudder in 2015 for Make A Wish

Urban Mudder 1 Urban Mudder 2

What is the cause for Cupid’s Undie Run?

It helps fund research towards NF – neurofibromatosis. 1 in 3,000 children are born with this genetic disorder. It causes tumors to grow non-stop on the nervous system, often causing deafness, blindness, disabilities and debilitating pain. You know what’s even worse? There is no cure and frighteningly few treatment options.

There are a lot of NF-focused charities out there that have different, venerable missions. Some focus on patient care, the Children’s Tumor Foundation (CTF) focuses primarily on research and finding a cure. Cupid’s is a part of CTF, which has been a four-star rated charity from Charity Navigator for so long, that it essentially puts them in the top 2% of most effective charities in the country.

Anyone who hangs out here at More Cowbell knows Phil’s a friendly guy. He chose the Cupid’s Undie Run based on recommendations from friends. (Plus I think he wants an excuse to go streaking around NYC.)

He said, “I thought it sounded fun, had a great cause to run for, and also I wanted to try out something that combines athleticism along with some hilarity! I mean, c’mon, I’ll be running in my undies! How cool is that? Undies! I bet everyone wants to see me running almost naked. (Okay, maybe some actually don’t.)

“The bad thing is that it’s in the dead of winter, so of course I am worried about shrinkage. I better stuff in a few socks if you know what I mean.”

Ten reasons why this run is completely cool.

Note: If you would also love to run in your underpants, there are events in nearly 40 cities around the world. Their tag line: “We attract heroes, party animals, undie-lovers and the generous-as-hell. We’re fighting NF, a rare and deadly disease that affects 1 in every 3,000 births. We will win. Are you in?”

Donate to the cause and sponsor Phil by clicking here! Every dollar counts.

And since this is More Cowbell, and enquiring minds want to know all manner of things, I asked Phil a few more questions…

Do you have an undie favorite?

Even though I sleep in the nude, I prefer low rise men’s bikini style during the day. I say, “No Way” to tighty whities or boxers. Yuck.

What is your favorite running gear?

Normally just a tight Under Armour workout muscle shirt, basketball shorts, and running shoes. But in this case? It will be undies.

How do you train for these runs?

I am a gym rat. Always have been. Weight training at least 5 days a week. Running nowadays around 3 days a week which normally includes a distance of 3.2 miles so I am basically running a 5K each time.

Funny thing is I always hated running, but to stay in shape and keep my figure in check, it’s a must. Cardio is key considering all the eating, drinking, and partying I do here in NYC. I have learned to actually like running more now – it helps to clear my mind while I listen to my music. Plus, living on the Upper East Side of Manhattan, I run along the water which offers great views.

Also, as age becomes a factor it’s crucial to keep the metabolism revved up as we get older to stay lean and fit. I gotta stay sexy for the ladies!

Whether it be $5, $50 or $5,000… all donations help and go a long way toward helping those in need. Oh yeah, and they’re tax-deductible, too.

*  *  *  *  *  *

And there you go – a dude we love, undies and a fantastic charitable cause. It’s a trifecta of awesome. Here is the link to Phil’s fundraising page:

Would you run in your underpants? (Like in public.) Had you heard of neurofibramatosis? What’s your favorite charitable organization? Enquiring minds love to know these things here at More Cowbell!

~ Jenny

About Phil

Phil Holtberg

Phil Holtberg is an advertising and sales guru with close to 20 years in the biz. With a varied background which includes stints as a certified personal trainer, bartender, small business owner, ad rep, publisher and writer, Phil brings his overall life knowledge, opinions, humor, and everyday experiences to light on his blog, The Regular Guy NYC.

Follow his fun journey via his Facebook page or on Twitter.

About Jenny Hansen

Avid seeker of "more"...More words, more creativity, More Cowbell! An extrovert who's terribly fond of silliness. Founding blogger at Writers In The Storm ( Write on!
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29 Responses to Cupid’s Undie Run – a More Cowbell Kind of Event

  1. K.B. Owen says:

    Awesome, Phil! Hubs and I are in. Donating with Paypal was quick and easy (WAY easier than running outdoors in February in our undies!).

    Good luck! Who knows? Might be a great way to meet the ladies (depending on how many socks you use). *wink*

    Liked by 2 people

  2. Catherine Johnson says:

    Awesome! He sounds like my sister. She’s about to do the London marathon (which I always said I’d do lol) and then a quadrathlon in Sweden.

    Liked by 1 person

  3. Hey Jenny!

    I am totally humbled and so appreciative that you chose to feature me on your blog, and help support my charity cause. Wow – what can I say? I better pick out a smashing outfit and some sexy undies to show off in. Plus, even though it’s winter, doing this for a great cause helps ease the sting of the cold air a bit. As George Costanza experienced shrinkage long ago I hope to not repeat that! 😉

    Thank you! Thank you! Thank you!

    Liked by 1 person

  4. Go Phil Go! And take pictures while you’re at it.

    No, I would not run in my underwear. Not because of the underwear part, because of the running part. But, I do love these obscure charities (obscure to me anyway) so I participate in other ways (such as a monetary donation). So, yay Phil! You run, I’ll pay.

    Patricia Rickrode
    w/a Jansen Schmidt

    Liked by 2 people

  5. davidprosser says:

    Awesome Phil. Well done, it sounds a great cause.

    Liked by 2 people

  6. Jane Sadek says:

    Honey, I don’t run – period! Great addition to the Undies Chronicles.

    Liked by 2 people

    • Hi Jane!

      Funny thing is that I really don’t like running all that much, but it does help me burn off all the beer and bad foods I eat living here in NYC! Gotta look good in my undies!

      Liked by 1 person

    • Jenny Hansen says:

      You sound so Southern here, Jane. I love it! And I don’t run either, thanks to my orthopedic surgeon. When he fixed my hip, he said, “Please don’t screw up my great work on this. Walk! Don’t run.” Music to my ears…


  7. So good of you to post about this, Jenny! I hit the “donate” button on Phil’s blog the first time I read about his undie run! Trust Phil! Every year he devotes himself to raising money for some worthwhile charity and I’m happy to support him. He puts his heart and soul into each of these events. I’m not going to speculate as to the undies he chooses for the run. I’m just going to close my eyes and cheer really loudly for him! Go, Phil!


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