Pocket-Sized Dates You Can Carry With You All Season Long
The holidays are pure magic… and also pure chaos. Between work parties, Christmas concerts, family gatherings, and endless errands, it can feel like there’s barely time to breathe — let alone squeeze in a date night.
That’s exactly why I loved the idea my sweet friend Jessica at work shared with me the other day. She told me she keeps a handful of “pocket-sized” games and activities tucked inside her purse so she and her husband can sneak in mini date nights anytime, anywhere.
Genius, right?!
So naturally, I had to give that idea a holiday spin. 🎅🏻✨ Imagine you and your spouse laughing together while waiting in line for hot cocoa, asking flirty questions in the car before heading to a family party, or killing time during Christmas shopping with a mini game that reminds you why you’re teammates.
Table of Contents
The Pocket Date Kit: Tiny Games for Big Love
Okay, now let’s get to the fun part — what actually goes in a Pocket Date Kit!
When Jessica first told me she carries tiny games in her purse, I immediately thought, “UM, that is brilliant…and also extremely marriage-goals.” Because honestly? We don’t always have hours to plan a date night, but we do have little pockets of time throughout the day — in the car, in line, waiting for food, hiding from our kids in Target’s candle aisle… you know, the usual.
So I started collecting tiny, toss-in-your-bag games that Nic and I could pull out on a whim. Nothing big, nothing complicated — just small, playful moments that spark connection in the middle of holiday chaos. These little games pack a big punch in the love department, and they’ve quickly become one of my favorite ways to sneak in time together.
- We’re Not Really Strangers – Couples Edition: Pull out a few cards while you’re waiting for your peppermint mocha or sitting in the car before a holiday party. Each question gets you laughing, reminiscing, and connecting — no deep setup required.
- Love Lingual: This mini deck is basically couple’s therapy in your pocket — only way cuter and faster. Perfect for road trips, lines, or cozy fireside chats.
- Travel Qwirkle: A pocket-sized version of the classic tile game! It’s easy to play on a coffee shop table while sipping cocoa or waiting for your kids’ Christmas recital to start.
- World’s Smallest UNO: You can’t go wrong with UNO, especially when it fits in your hand! Keep score across the whole season — loser has to buy the next round of hot chocolate.
- Mini Dice or Tiny Deck of Cards: Toss these in your purse for spontaneous fun anywhere. Play a quick game of “War,” roll for dares, or invent your own “Lucky in Love” challenges. (Example: Roll a 6? You get a kiss.)
- OK Play: This one is ridiculously easy to learn and even easier to carry — the whole thing clips right onto your bag! You can play anywhere: a coffee table, a car hood, a bench outside Target… wherever the holiday chaos finds you. It’s fast, competitive, and surprisingly addictive. If you want a game that’s simple, portable, and guaranteed to spark some playful trash talk, this is it.
- Mini Doodle Pad or Etch-a-Sketch: Challenge each other to doodle something festive — like a snowman, a Christmas cookie, or a portrait of your spouse. Bonus: the worse the drawing, the better the laugh.
- Trivial Pursuit Mini Packs: These little Trivial Pursuit Mini Packs are tiny, clever, and SO much fun to whip out while you’re waiting in line or sitting through yet another holiday recital. Each pack is themed, so you can choose your vibe!
- Games On the Go: This little deck is such an underrated gem! Even though it’s designed for families, it’s perfect for couples who want something fun and low-pressure to play while traveling, running errands, or waiting for the next holiday event to start. It comes with 50 mini games — everything from silly guessing prompts to trivia, word challenges, memory tests, and quick scavenger-hunt style searches.
- Scrabble to Go: If you love word games but don’t want to haul the whole Scrabble board around, Scrabble to Go is such a fun alternative. Scrabble To Go is the cutest little travel version of the classic game we all love — and it’s perfect for tossing in your bag during the holiday rush.
Make It Yours: DIY Pocket Date Kit
One of my favorite things about this whole pocket-date idea is how easy it is to personalize. Yes, you can absolutely toss a few mini games into your purse and call it good — but if you’re anything like me, you’ll want to add a little extra you into the mix. That’s where a DIY Pocket Date Kit comes in.
Think of it as your own tiny “love on the go” bundle — a little pouch filled with the things that make your relationship feel fun, flirty, and intentional. You can customize it with prompts your spouse would love, tiny treats they always grab at the gas station, or sweet little surprises that turn an ordinary moment (like waiting in line for holiday drinks) into something special.
And the best part? It doesn’t need to be complicated or fancy. A small zipper pouch, a couple of printable cards, a pen, and one or two thoughtful touches are all it takes to build a mini kit that feels so personalized. This is such a cute way to sprinkle connection into the busiest season — and it makes every little errand feel like a chance to flirt or laugh together.
Ready to make your own? Here are a few simple ideas to get you started.
- A few printed conversation starters (holiday-themed or flirty!)
- A tiny notebook and pen for writing love notes or “holiday bucket list” wishes
- A couple of candies (peppermints, Hershey’s kisses, or candy canes — you get it 😉)
- Mini dares written on index cards. Things like “Whisper your favorite holiday memory” or “Sneak a kiss under the stars.”
You can even make one for your spouse’s glove box so you’re both prepared for impromptu fun!
10 Quick + Flirty Pocket-Sized Challenges
And because mini games already make this whole idea adorable, I had to add one more layer of fun — quick, flirty challenges you can do literally anywhere.
These are the little “love missions” you can complete while running errands, grabbing cocoa, driving around looking at Christmas lights, or trying to survive yet another holiday event. They’re fast, fun, and guaranteed to make you feel like teammates again (or at least like two people plotting something cute together).
Think of these as tiny sparks — simple moments that turn ordinary holiday errands into unexpected connection.
- Compliment Countdown — Before you finish your next errand, give each other three sincere compliments. Bonus if one makes you both laugh.
- Mistletoe Mission — Find anything that could pass as mistletoe and kiss under it. (Holiday wreath? Tree branch? Totally counts.)
- Festive Flashback — Whisper your favorite holiday memory together — and recreate one little part of it.
- Sneaky Note Swap — Write a tiny love note and hide it in your spouse’s pocket, wallet, or purse.
- Warm-Up Challenge — Hold hands for one full minute, no matter where you are. (Parking lot, checkout line, doesn’t matter!)
- Elf Energy — Pick one random act of kindness to do together before the day ends.
- Flirty Forecast — Predict how the night will end (wink). Whoever’s closer wins a kiss.
- Candy Cane Compliment — Grab a candy cane (or any holiday treat). Share it Lady-and-the-Tramp style.
- Car Carol Karaoke — Sing one Christmas song at the top of your lungs together. Even better if you make up your own lyrics about each other!
- The Gratitude Game — Say three things you’re grateful for about each other before bed tonight.
Happy Holidates!
The best part of these pocket-sized dates isn’t the games — it’s the moments.
The small, ordinary pauses where you look at each other and laugh. The “I see you” moments when the world feels busy but your love stays simple.
So this season, don’t wait for the perfect date night. Pull out your pocket kit, order that peppermint mocha, and make connection happen right where you are. 💕
