Your mission
The Porch Portrait Reveal
Carve a portrait of your secret friend, keep it hidden until Halloween, then line every pumpkin up glowing on the porch. Everyone has to find their own face and guess who carved it.
Bonus challenge: Hand out goofy awards like Spitting Image, Most Dramatic Eyebrows and Looks Like Someone's Uncle.
Gather your friends, swap photos and carve each other's faces into pumpkins. You trace a printed photo straight onto the skin, then scrape and cut the shapes. On Halloween, you light them all up on the porch and watch your best friend's grin start glowing orange.
Picture a row of pumpkins on the porch where every one is somebody you know. There's your roommate's crooked smile, your sister's big eyebrows and your buddy mid-laugh, all glowing in the dark. Everyone draws a friend's name, picks a photo of them and turns it into a carved portrait. You never draw freehand. You trace the printed photo, so if you can follow a line, you can do this. Then the pumpkins wait for Halloween and one big reveal.
Carving a friend's face means looking closely at them for a whole evening: the dimple, the eyebrow, the way their smile tips to one side. It's a goofy, sweet kind of attention. When they spot themselves glowing on the porch, they laugh like someone who feels seen. It's the funniest compliment you'll ever carve.
Top gear to make this quest great.
Pull it off
Each person needs their own canvas, and a flat side keeps the face from looking stretched.
Small saws make tight curves around eyes and smiles much safer than a kitchen knife.
They make the faces glow without a flame near costumes on a busy porch.
As an Amazon Associate I earn from qualifying purchases. Prices may change.
If you can tape paper to a pumpkin, you're halfway there. Essential: one smooth pumpkin per person with a nice flat side for the face, a pumpkin carving kit with mini saws, a scraper and a poking tool, a black-and-white printed photo of each friend, tape, and battery pumpkin lights. Handy extras: a clay loop tool, which makes scraping soft shading easier; flour, to make your traced dots easy to see; and newspaper, because the guts get everywhere.
A good quest stays a good story. These are general notes; your gear's manual, the venue's rules and local law come first.
First comes the secret part. Everyone writes their name on a slip of paper and draws one from a bowl. That person is your subject. Find a clear, front-facing photo of them, turn it black and white, and boost the contrast until the face is just dark shapes and light shapes. Print it as big as your pumpkin's flattest side.
Time to get that face onto the pumpkin. Cut a hole in the back or bottom, then grab the scooper from the CHRYZTAL kit and dig out all the slimy guts. Scrape the inside of the front wall to about an inch thick. Tape your printout on and poke little holes along every line, about a quarter inch apart. Peel off the paper and there's your friend as a dot-to-dot!
Here's the trick that makes it a portrait. The dark parts of the photo stay as skin. The medium parts get the orange skin scraped off so they glow softly. The suiwotin clay tools are perfect for this: each end has a flat wire loop with a sharp edge, so you can shave off skin in thin curls without poking through. The brightest bits, like teeth or the shine in an eye, get cut all the way through. Saw slowly with small up-and-down strokes, always moving the blade away from your hand.
Want to see it come alive? Switch off the lights, pop a battery light inside and step back a few feet. If a cheek looks too dark, scrape it a little thinner. If something looks right, leave it alone. Keep your pumpkin turned away from your subject so the surprise stays safe until Halloween.
It's Halloween, and the gallery opens tonight! Tuck a Homemory flickering tea light into each portrait. Just slide the switch on the bottom and it starts to flicker like a real candle, and each one runs over 200 hours, so your faces can keep glowing night after night. Line every portrait up along the edges of the porch steps and gather everyone out front. One by one, each person hunts for their own glowing face and guesses who carved it. Then everyone steps back together to take in the whole row.
Before the trick-or-treaters arrive in force, celebrate your gallery. Hand out silly awards like Spitting Image, Most Dramatic Eyebrows and Pumpkin Most Likely to Wink. Then take a group photo with everyone crouched behind their own glowing face. Afterward, keep the pumpkins somewhere cool so they last a few more nights.
You turned your friends into a glowing porch gallery, one carefully carved face at a time. Snap the group shot and challenge another crew to carve your faces next year.
You bring the curiosity. We've found the tools.
Pull it off
Each person needs their own canvas, and a flat side keeps the face from looking stretched.
Small saws make tight curves around eyes and smiles much safer than a kitchen knife.
A set of mini saws, a scraper and a poking tool.
Get on Amazon · $17.98 — Pumpkin carving kitwhat to look for & our pick →
They make the faces glow without a flame near costumes on a busy porch.
Flameless LED tea lights or pumpkin lights.
Get on Amazon · $19.99 — Battery pumpkin lightswhat to look for & our pick →
They shave off thin layers of skin so cheeks and shadows glow softly.
Small wire-loop scrapers made for sculpting clay.
Get on Amazon · $7.39 — Clay loop tool setwhat to look for & our pick →RELATED GEAR GUIDE
Tabletop RPG Starter Kit: 10 Picks That Earn Their Table Space
Practical picks, real prices · Social & Community
As an Amazon Associate, IRL Sidequests earns from qualifying purchases at no extra cost to you.
Prices and availability are subject to change. The price shown at checkout on Amazon at the time of purchase will apply.
Hand-selected quests our team thinks you'll love
Your people are out there, probably within three miles of your house.
Stop scrolling, start connecting. Strategic field guide to finding genuine communities through skill-sharing, interest groups, and face-to-face meetups.
That cracked sidewalk planter doesn't need to stay dead—fill it with wildflowers at 2AM and watch neighbors smile for months.
Learn guerrilla gardening tactics to green up forgotten urban corners with native plants, seed bombs, and nighttime planting missions.
Getting better at talking is weirdly fun with friends
Round up six friends, drag some chairs into a circle in your yard, and spend 90 minutes getting genuinely better at talking to people. One skill, eight-minute pair rounds, a soft chime to switch partners, and a lot more laughing than you'd expect.
Not this one?
Tell the generator how much time you have, who you're with, and your mood — it picks from 500+ quests like this one.
Try the real life side quest generatorOr browse the full list of real-life side quest ideas or side quests to do with friends.