What do you get when you combine a bald retired financial consultant, a pink poodle skirt, and a love for philanthropy? You get Robert Shaffer as Pinky Penmark, of course!

You may know Shaffer as the “bald guy in a pink dress” who makes audience members laugh during Bingo nights at Punky’s on Central Ave in St. Petersburg. But there is so much more to his story.

OUTCOAST sat down with Shaffer (AKA “Pinky Penmark”) to learn about the history of Pinky, Shaffer’s community work, and how a childhood moment set him on the path to retirement at age 46.

Where did you grow up? 

Technically, I grew up all over Central and South Eastern Ohio. My father was in retail management and he was transferred several times in my elementary school days. We finally settled in Circleville, Ohio–Home of the Circleville Pumpkin Show, “The Greatest Free Show on Earth,” it’s called. We moved there when I was in 5th grade. Fortunately, my father was able to keep us there through 12th grade so my brother and I could graduate high school in Circleville.

To date, Circleville and St Pete are the two places I have lived the longest in my life. Circleville for 9 years and St Pete for 10 years now.

Share with us a memorable childhood moment. 

There are a lot of good ones, and my mother is going to hate me for saying this, but the most memorable one was during my Sophomore year in high school. That fall, a friend of mine and I were suspended from school for three days for experimenting with a little “Mary Jane” (marijuana) during a football game and while wearing our band uniforms.

Being suspended was not the happiest moment to live through, but it’s the single biggest catalyst that changed the direction of my life, my studies, and the sports in which I participated. Following that incident, I left band, got involved in the school newspaper, and developed my love of writing. I would have been a completely different person than I am today if not for that “Mary Jane Moment.”

You have a Bachelor’s in Journalism. Did you ever work in this industry?

Actually, I did not. I went to Ohio University because it is the best “j school” this side of the Mississippi. I loved to write, but my focus changed my junior year in college and I concentrated more on the PR and marketing courses within my journalism major. However, I did work for the college newspaper for two years doing a lot of feature writing. I even got to meet and interview Todd Rundgren, one of my favorite musicians and vocalists at the time. I recall thinking, “I’ve really arrived!”

Where did your career take you after college?

I sold my soul for many years and hobnobbed with the mostly-white, straight, male and very privileged banking class as a financial consultant with Merrill Lynch in order to flip the script and make a difference in my wiser years. I wasn’t crazy about the person I was then, but I knew I had to make good money so I could live and participate in a much better life later on. I engineered my exit to conveniently occur right before their takeover by Bank of America. I was only 46 and have never looked back.

Robert Shaffer, second to left, at Sarasota Pride (Image provided by Shaffer)

Tell us about your community work since retirement.

None of the things I do feel like work. Since retiring, I have been lucky enough to focus on the things I can do to make sure that my community and this world are better for generations that follow. I’ve long strived to make a difference in the LGBTQ+ community in which I find my sense of home and family.

I’ve volunteered with ASAP, now EPIC, since I first moved to St Pete. As part of my volunteer work with EPIC, I sit on the AIDS Walk Tampa Bay (AWTB) committee, helping to organize the annual walk that benefits EPIC.

I also spent two years volunteering for St Pete Pride and became the Operations Manager, which means I did a little bit of everything, but a lot of nothing. Laughs. It was fun and we made a difference. It was challenging also, which made it even more gratifying.

I’m now involved in the newest LGBTQ+ week of events, Come OUT St Pete. Somehow, I have morphed into the Pinky Penmark character, too, which affords me a great opportunity to work with a different local nonprofit every week. And it gives me a microphone, meaning I have the opportunity to talk with people loudly about current events and my take on the state of the world, nudging people constantly to do even more for others and lift up our community.

What led you to the Print Industry?

My transition to the print industry was totally by accident and by becoming friends with Jane Byers, the owner of Perfect Copy & Print, Inc.

A few years ago, when I was still the Operations Manager for St Pete Pride, a “shortish”, bubbly woman came up to me during an SPP vendor meeting and exclaimed, “I need four t-shirts”!! She really had no idea what sizes she needed though, so we chatted as we figured out which t-shirt designs and sizes she wanted. I remember feeling like we had this instant feeling of kinship.

Fast-forward two years, Jane has a print shop, I have a writing background, and Jane is needing some reliable and capable help because, until then, she had really been a one-woman show at Perfect Copy & Print for three years. I had the time, the inclination, and a little interest left over from college. I really liked Jane and our relationship grew organically from there. And here we are today.

Tell us about your role with Perfect Copy and Print.

At Perfect Copy & Print, “all hands on deck” refers to Jane and me. Every day is completely different because we handle everything, including marketing, sales, accounting, production, operations, social media, community involvement, cleaning the office, and taking out the trash. It’s never a dull moment or boring day at work.

Do you still write? If so, what is your favorite subject to write on?

My favorite topic to write on is, “What the hell is wrong with these people?!” I have always been curious about the basis for people’s beliefs and values that are so different, or even opposite, of mine. We all shake our heads when we hear odd opinions, attempts to marginalize minorities, or crazy political banter. So, I write to work out why people, groups, or political parties feel, act, or do what they do. Their actions aren’t random.

For me, writing removes my anger from situations and helps me find a path forward that might best bring change. In that moment, I can pretend to understand my opposition. Please note that this does not mean I have empathy for their actions or beliefs.

Tell us something that most people don’t know about you.

Outside of my home, I am extroverted, constantly engaged, and I talk to a lot of people in a week about a lot of topics. Very seldom is it that you find me with little to say.

But, when I get home and shut the door behind me, I don’t even want to answer the phone. I often very happily cocoon myself at home for several days at a time.

Pinky Penmark
Pinky Penmark at the Tampa Bay Ray’s Pride night in June 2017. (Image provided by Robert Shaffer)

How did your character, Pinky Penmark, evolve?

My mother graduated high school in 1959, so she was my catalyst for the decade in which Pinky “lives.” Mom always talked about wearing her poodle skirts on Saturday nights after she spent the day starching it over and over in order to achieve the maximum volume for her skirt. As a boy, I didn’t understand why I couldn’t wear one of these neat-sounding poodle skirts.

Decades later, Jane and I were making plans to go to the Metro Health and Wellness Annual Gala in September. We heard that the theme for the gala was going to be a 1950’s sock hop. Of course, I did the only thing I could do. I immediately called a friend at Metro to announce that wearing a poodle skirt had been a life-long dream and this was my opportunity to do to. I told my friend to expect me at the Gala in full poodle skirt ensemble.

Over the next week, I created the character of Pinky, Jane helped me put together an outfit, and Miss Pinky Penmark was ready for the Ball. We had a heck of a time at the Gala and the following day “Pinky” went on a shelf in the back closet because she was never intended to be more than a one-night creation.

A few weeks later, we held the AIDS Walk Kickoff Party at Punky’s and the next day I called Brian Longstreth to thank him for making Punky’s available to us for this event. To my surprise, Brian told me he was in need of a new Bingo Host and he thought that Pinky should be the one to do it. At first, I was thinking, “oh, heck no, I can’t do that,” but I met with Brian and he sold me on the idea by insisting that I book the events and work with the charities to promote the fundraisers. Brian knew it would be hard for me to turn down an opportunity to work with a new nonprofit every week. It worked. Two weeks later, I dusted Pinky’s first outfit off and became the new Host of Bingo4Charity at Punky’s Bar & Grill.

When did the bingo charity events at Punky’s start? 

I began hosting Bingo4Charity at Punky’s Bar & Grill on November 30, 2016, though Bingo4Charity at Punky’s has been around since Punky’s opened in late 2015.

How many charity events do you host a year as Pinky?

Well, there are 52 Bingo4Charity nights at Punky’s in a year. Then there are Dining Out for Life events. Plus, during the months leading up to the Tampa Bay AIDS Walk, I do promotional events for them. Throw in Come OUT St Pete events and add to that my newest endeavor, the Mid-term Elections in 2018, and I have no idea what that total would be, but it’s a lot. Pinky’s just a little crazy like that.

Which of these has been your favorite?

I am going pass on picking a favorite because I am constantly meeting so many new, fun, and like-minded people through Pinky’s shenanigans, but I will say that running around Tropicana Field as Pinky during Pride Night at Tropicana Field in June was surely one for the highlight reel.

Which event has raised the most money?

In my tenure, it’s a close tie between Pet Pals Animal Shelter and The Kind Mouse Productions. However, just a few weeks before Pinky began hosting Bingo4Charity, my fellow AIDS Walk committee members organized the 2016 AWTB Kickoff Party followed by Bingo4Charity benefiting AWTB. Those combined events raised the most in one evening that I am aware of. That event is upcoming again on November 8th at 6pm at Punky’s Bar and Grill.

I’m sure you’ve seen it all at these events. Care to share any fun stories?

You’re right. There are lots of funny stories in the 40 or so Bingo4Charities I have hosted, but the funniest moments involve the combination of righteous indignation and embarrassment people display after coming forward with, what they believed was a winning game card, only to learn that they made an error and are missing a number. These players will often actively attempt to bargain with me to allow their error to slide, and it always leads to some good fun Bingo shaming of them by myself and the crowd.

Pinky Penmark
Pinky Penmark decked out in her black poodle skirt and purse.

Does she always wear the pink dress? How many dresses does Pinky own?

Right now, Pinky has three pink dresses, one pink poodle skirt, three black dresses, and one black poodle skirt. Of course, the black pieces are decorated with pink accents. Pinky also has numerous sweaters, jackets, boas, and pieces of jewelry. She also has seven pairs of glasses, a Pinky name tag, and a few pairs of saddle shoes. Wow, that’s quite a collection in less than a year.

I’ve noticed that you keep the bald look during your performances. Any reason why?

A few reasons. Pinky is a character, not a drag queen personality. I would never compare myself to the artistry of the drag queen community. I lay zero claims to the creativity, dedication, artistry, and talent of those ladies. I don’t do makeup either. To me, makeup would mean that I would also have to do hair, and to me, the line between a character and a drag artist would then become a blur for the audience. Pinky’s not up there with them. And I don’t mean that in a self-deprecating way. Pinky is just Pinky. She’s a little odd and unique.

When you aren’t at the print store or dressed as Pinky, what are you up to?

Beating my head against the wall as I try to create ads, posts, calendars, and event covers for Bingo4Charity in Photoshop. Those things take me an unbelievable amount of time because prior to Pinky I had never used Photoshop or an Adobe Design product.

We are all excited about Come Out St. Pete. Can you fill us in on some details?

Our local LGBTQ+ community has become so visible, so strong and so large that when a group of us were gathered together by Brian Longstreth, we concluded that St Pete is able to support, and actually needs, another weeklong series of LGBTQ+ activities to remind us that living visibly as our true selves is the only way to maintain the momentum we’ve enjoyed in recent years during the vast expansion of LGBTQ+ civil rights.

The series of events called Come OUT St Pete are centered around National Coming Out Day on October 11th. There will be family events, kid events, picnics, movies in partnership with TIGLFF, a march, the Taste of Grand Central, and much, much more. A full listing of planned events is on both the Come Out St Pete and Pinky Penmark Facebook pages, as well as on both websites: www.comeoutstpete.org and www.pinkypenmark.com.

Where can we see Pinky next? Outside of Punky’s Bingo, where else does Pinky go/perform?

For the next six weeks or so, I am slowing it down a bit, so through the end of September, you will only see Pinky at Bingo4Charity on Wednesdays. After that, we will be in full swing promoting Come OUT St Pete and as a result, for the first two weeks of October you will see Pinky all over town and see very little of Robert.

A few weeks later, Pinky will be hosting the Tampa Bay AIDS Walk 2017 Kickoff Party on November 8th. From that point, up until the walk on December 9th, Pinky will be at the Saturday Morning Market and Barnes and Noble, on a regular basis, to promote the walk.

And of course, every Wednesday night, Pinky will be doing her thing at Bingo4Charity.

Pinky has a huge announcement come January 2018. She’s come up with a way she hopes will keep people educated, informed and engaged with the midterm elections without them feeling a sense of the political burnout so many of us are feeling presently.


To learn more about Pinky Penmark, click here.

Pinky will also be a guest of honor at OUTCOAST’s Stories of Pride Kick-Off Experience on October 24th. To purchase tickets, click here.