Rivendell Theatre Ensemble Presents DO SOMETHING PRETTY Review - Teenage Life On The Brink of Change

TLDR: A reflection of a very specific time period and the attitude about sex and relationships during that time, Do Something Pretty shows a brief point in time for one pair of sisters and two guys in their life. The show is a character driven show that leans into realism to create this view peering into one day in their lives.

Life in the 90s

When times were simpler, right? You’d come home after school, your parents are still at work so it's the perfect time to grab the bag of Doritos and rot your brain to music videos on MTV. Piles of VHS tapes sit by the tube television sitting in this peak 90s suburban home’s living room. Two teens, well one teenager and one tween, sit on opposite ends of the floral print couch not saying anything to each other. One dressed in a Smiths T-shirt, pants held up by a tightly cinched belt, and an oversized trench coat. The other one in cutoff jean shorts, a tank top, and topped off with a side ponytail.

They're both waiting. Waiting for time to pass. Waiting for the other sister to come home. Waiting for something, anything, to happen. And so begins Do Something Pretty. We see a day in the life played out in real time during this seemingly innocuous day.

As Jason and Phoebe (Reilly Oh and Katherine Mallen Kupferer) wait for Phoebe’s sister to come home, we watch their meandering conversation. Phoebe pries more out of Jason and we find out about their current lives at home. She’s nervous about him smoking in the house, but eventually asks to try pot with him for the first time. Evie (Jocelyn Zamudio) bursts home from her fast food job and we're taken further into their history. She and Jas have been friends since forever, but he wants more. She's always had a history of dating terrible men. Phoebe hates being left alone all the time. Jason’s repeating the twelfth grade and Phoebe’s just starting high school. Rushing to get ready for a date sets off the chain of events that causes things to shift and change as they look towards the future.

The Raw Feelings of Being a Teenager

Between these two sisters and the two boys, we feel entrenched in what teenage relationships were like during this time. There’s real vulnerability from the cast as they play these teenagers grappling with change, but also we see the reflection of the attitudes of the time around women, masculinity, sex, and their relationships.

Kupferer as Phoebe plays a believable 14-year-old as she tugs nervously at her clothing or says something that feels naive to us, but we know for her it's coming from a genuine place of being at that age.

We bounce between feeling sorry for Jason to judging him as we see the frustration brewing in him as Oh sits, waiting for Evie. He plays the quintessential “nice guy” perpetually waiting in the wings, and we hope he may turn out different than all the rest.

We’re given a picture of Evie through Phoebe and Jason’s conversations, but as Evie comes home we see more from her than just a partying teenager. She’s working hard to be able to leave this town, yet doesn’t believe she’s the girl worth going the extra mile for.

And through her interactions with Matt (Jasper Johnson), we see the opposite of Jason as he saunters into the house full of LA vibes and casts his own judgements on Jason against his measure of manlihood.

Throughout it all, we recognize these situations and are comparing it to today’s world. We keep thinking, we may not have these exact feelings anymore, but have we actually gotten that much further?

The After Party Thoughts

Plotwise, there’s not a lot of action that happens in Do Something Pretty. And yet there’s so much that happens in this singular chain of events that show us a reflection of life in this specific time period.

Do Something Pretty speaks to a specific experience that perhaps many cis-women will recognize and it might open others’ eyes to an experience they may not have realized happened around them. We see the reflection of the next generation in Phoebe, one that is prone to repeat the same cycle, but we hope she’s able to break it. There's a lot of social commentary packed into this play that’s left up to audience interpretation of what comes next.

For those that are looking for a more action-packed play and aren’t so much into character-based plays, this show may not be for you. However, for those that have lived through the “nice guy” era and like plays that paint a realistic picture of life at a specific point in time, Do Something Pretty would be a good fit fit for you.

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When

Now through June 7, 2026

Where

Rivendell Theatre

5779 N. Ridge Avenue

Chicago, IL 60660

Runtime: 2hrs with intermission

Tickets

$28+

Tickets can be purchased by calling the box office (773) 334-7728 or through the Rivendell Theatre Ensemble website

Photos

Michael Brosilow

Find Allie and The After Party featured on Theatre in Chicago

CAST

Katherine Mallen Kupferer (Phoebe)

Jasper Johnson (Matt)

Reilly Oh (Jason)

Jocelyn Zamudio (Evie)

CREATIVE

Melissa Ross (Playwright)

Jessica Fisch (Director)

Daira Rodriguez (Assistant Director)

Lindsay Mummert (Scenic Design)

Saawan Tiwari (Costume Design)

Sierra Walker (Lighting Design)

Eric Backus (Sound Design)

Sarah Slight (Dramaturg)

Caroline Michele Uy (Associate Dramaturg)

Rita Vreeland (Stage Manager)

Pat Fries (Artistic Producer)

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