A Year of Dating Disasters | Jennifer Theby-Quinn stars in The Twelve Dates of Christmas at Westport Playhouse

Photo of Jennifer Theby-Quinn by Peter Spack

We have had to endure some rough times lately. The Westport Playhouse is looking to lift your spirits with the one-woman show The Twelve Dates of Christmas. Jennifer Theby-Quinn stars in the one-woman production (written by Ginna Hoben) as Mary, a recent dumpee, who spends the next twelve months on an emotional rollercoaster.

I felt like my Christmas came early when I was given the opportunity to interview Theby-Quinn, a decorated veteran of the St. Louis theater scene. Here is our conversation about her career, the production, and work-life balance.

Are you originally from St. Louis?


That begs the questions which high school you attended.

Ha! I went to St. Joseph’s Academy, an all-girls prep school run by Sisters of St. Joseph’s of Carondelet. Then I went to college at St. Louis University. I have an undergraduate degree in Theater Performance and an undergraduate degree in Theological Studies. and I have a Master’s degree in Theology with an emphasis in New Testament Biblical Literature.

Ooh, she educated. Do you remember your very first theatrical production you were ever in?

Yes! The first production I was ever in was freshman year of high school, so I was late when it comes to a lot of, like, professional folks who start doing stuff with community theaters when they’re really young. I didn’t start doing anything until high school. So I started my freshman year, I did Jesus Christ Superstar.


Right? You have to do it. I did it at De Smet Jesuit High School. I did shows there for a couple years and then I hopped over to CBC and worked with Tom Murray for a little while before college.

Do you remember your first paid gig?

That’s a great question!

The reason I like to ask this is because my husband is an artist. He has done art for years for his own pleasure. When someone offers to buy one of his items, his eyes light up not due to the money, but because someone is appreciating his work.

I’m also a vocalist, so I started working gigs in college. I remember during my sophomore year of college Oregon Catholic Press, which is a recording studio, flew me to Chicago to record something for a label for them. That happened when I was 19. I did some other gigs with World Library Publications where we ended up performing in the RCA Dome. That was when I was in college.

I didn’t take my equity card until right before the pandemic. I camped out in non-equity land for a long time because I was working so much. But my first paid theater gig was probably when I was in college.

Speaking of the pandemic, how did that affect you personally as a performer?

Oh, it was horrible, devastating.

We were three-quarters of the way through a run of Flanagan’s Wake. We were having a great time. It’s an Irish Wake set in a pub and it’s just a hoot. The shutdown was right before St. Patrick’s Day, so we had a special show lined up for the holiday. We had some really huge houses. We were getting some really great traction. Our improv was just starting to really cook because we’d been in the space long enough and in the show long enough and then we went from a Saturday night show to a day off on Sunday to a phone call on Monday saying, “Hey, we’re done.”

I was booked for like three months after that, and then I had booked for the summer, and then I had booked for the fall, and then I had booked the following winter. So I had like a year’s worth of work just to go up and smoke. That was not just income, but health insurance. And all of the other things that come with work.

The thing I love about the theater is that the theater endures and I would imagine you guys have come back twice as strong.

We’re coming back. Audiences are coming back. Theaters have had to adjust because the financial picture is different now than it was when we shut down. But you know, we’re creative people. This is what we are here on the planet to do: to create things. We are creating theater in new ways and reaching audiences in new ways, which means we’re reaching new audiences. People that maybe have never been in the theater before or haven’t experienced it the way that we’re ready to do it now.

I know you have been involved with St. Louis’ Shakespeare community. What was your favorite Shakespeare in a role that you ever got cast in?

Ooh, That’s so hard. I love Much Ado About Nothing. That is just a show that’s very near and dear to my heart. I did it two years in a row. I did it with St. Louis Shakespeare. I played Margaret and loved it. Someone from the festival saw me do it and asked if I would come and do it at the festival. She’s just such a brassy, sassy, broad, and I fit really nicely into the brassy sassy broad category.

What are some of the St. Louis theater companies you have worked with in the past?

I most recently worked with Upstream Theater. I’ve worked with Moonstone Theater, I was in their inaugural production last fall. I’ve done a couple of educational departments, so I did some ITC [Imaginary Theatre Company] stuff with The Rep. I’ve also worked with The New Jewish Theater a lot before they dropped their equity status. I’ve also worked with R-S Theatrics a bunch of times. I also worked with Metro Theater Company. I love what they do as a company.

You are no stranger to the Westport Playhouse.

That’s where I did Avenue Q for about four and a half months. I like the black box theaters, and you can’t really get much more intimate than the Westport Playhouse.

Photo of Jennifer Theby-Quinn by Peter Spack.

Let’s talk about The Twelve Dates of Christmas. How did this play cross your path?

That’s a great question for Lee Anne [Matthews – Artistic Director of the Westport Playhouse]. I have no idea where she got it. She called me one afternoon, probably two months ago and was like, “Hey, what are you doing during the holidays? I’ve got something for you to look at.” So she sent me the script. I read it in, you know, a single sitting, and I was like, “That’s sweet.” It’s kind of like a mishmash of stand-up and a Hallmark movie.

Have you ever done a one-woman show before?

Yes. I did a one-hander [“Iphigenia In Splott”] with Upstream Theater Company last winter. Totally different kind of genre that was much more in the world of—I don’t wanna say a political piece, but it was much more heart-wrenching. You go on this journey with a young woman who is from Wales, she’s poor, she’s uneducated. She finds herself in some pretty dire situations and you’re just along for the ride, right? It was like a kind of a rip-your-heart-out, emotional rollercoaster for a couple of months.

I did that in January and February with Upstream, so I have a sense of “You know, I know how to do this, at least in a sense.” Having done it before, I expect this to be totally different because it’s a totally different style. This is much more sweet and silly. She’s just a little bawdy, a little cynical.

But she’s also been dumped on Thanksgiving day by her fiancé. Then you kind of go through the year with her—a year’s worth of holiday disasters. And then you just go with her on a yearlong journey and you end up back at the holiday season the following year. There’s great little turns, little things you expect and things that you don’t expect. It’s just a very, very sweet holiday show.

My biggest question about a one-person show is how you even be to mentally prepare for this kind of role.

It’s definitely an endurance sport. It’s a marathon, not a sprint. I do a lot of homework. I started working on the show about a month ago and I work every day. I have a line learner app that I record the show into, and then I just put my earbuds in. I am listening to the show on repeat pretty constantly. That’s really helpful for auditory repetition.

I also have a very strong support system. My husband is really amazing. He holds the script for me and when I say, “and then,” and it’s actually “after that,” he lets me know. So he’s really great at helping me get things on my feet. Then once we start rehearsal, I will start putting things in my body and locating them in physical space, not just mental space, not just vocal space. Those things will help to solidify the storyline. We also have a three-month old now, so, yeah.


Thank you very much! Time is short across the board.

Wait. You have a three-month old and you are trying to memorize a one-woman show. Are you a sadist?

Maybe. Maybe I might be, Yeah, I don’t know. I guess we’re gonna see.

Photo of Jennifer Theby-Quinn by Peter Spack.

Let’s talk about the energy of the show. When you’re the only person on stage, how delicate is that balance of energy to you as a performer?

It’s incredible. It’s something that I’ve been thinking about a lot because with the show I did with Upstream, it was the kind where the character walks in, kind of grabs you, and you are on the rollercoaster, whether you wanna be on the rollercoaster or not.

With this one, comedy is different. Comedy is harder. Not everybody thinks the same things are funny. Some people will watch me and think, “Oh my God, she’s hilarious.” And some people will watch me and be like, “That woman’s annoying.” And then there’s like 1,001 different options in between.

So playing to different audiences every night means different audiences are gonna think different things are funnier. It’s a little bit like taking the temperature of the room every time you step out there. The first couple of moments are just me trying to figure out who are these people? Where are these people? Are they hungry? Did they go to the bathroom? Did they wish they grabbed another glass of wine? Did they just get dumped? Or are they thinking about dumping someone? Do they love the holidays? Do they think the holidays suck?

All of those things affect the energy in the room. Large houses aren’t always better than small houses. Sometimes they are, sometimes they’re hard to wrangle. Sometimes the small houses are like, “We are with you.” They’ll fill a space with their energy and their laughter, but, I have to hope that anyone who comes to a Christmas show during the Christmas season called the “The Twelve Dates of Christmas” has to be kind of just game for a good time.

Is there a point in this show where you know that, “I hit this point, I’m good.”

I don’t know the answer to that. I don’t have the energy arc yet. There is a point in the story where everything kind of culminates, but it is very late in the story. It goes from kind of laughing and silly to something that’s very poignant. I believe that scene will be very affecting. I suspect that people will identify with one of the people that I’ve dated earlier on and be like, “Oh yeah, I dated him too,” you know?

Time for some quick answer questions. Ready?

Of course!

Who is your favorite St. Louis actress?

Amy Loui. Oh my gosh, she’s fabulous. I can’t watch her without learning something. If I could be half the performer she is, I would be a happy camper.

Who are some of your favorite directors?

Julia Flood at Metro Theater Company is a visionary. The way that she treats theater for young audiences is unlike anything I’ve ever experienced. Patrick Siler and I have really great chemistry. We understand each other on a really weird level, and it makes working with him very fun and interesting. Edward Coffield. I mean, I’ve worked with Edward more than anyone else in the city. I love him.

What’s your dream role?

Oh my God. I don’t know. I mean there’s just, there’s just so much out there, you know? I would really like to play Lady M[acbeth] in the Scottish play. Yeah, I think I have the cojones to do it. That’s a badass right there. And you know, a husband to manipulate, a king to murder.

I also love to give some love behind the stage. So what theater company has been one of your favorite experiences to work with? All around from, you know, the dressing rooms, to the grips, to the sound people.

Upstream is phenomenal. The New Jewish Theatre is phenomenal. St. Louis Theater people are awesome. They’re just really great people.

The Twelve Dates of Christmas plays the Westport Playhouse from November 25th through December 23rd. Shows are 7:30pm Wednesdays through Saturdays, and 2:00pm on Sundays. Tickets are $34. You can purchase tickets through www.thewestportplayhouse.com. | Jim Ryan

Content notes: Age restriction : 16+ / Adult language

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