The Awkward Years Date Night Playlist
Turn up your boombox and get ready to dance like nobody’s watching! Put this playlist on shuffle as you go through this date night together – but promise us you’ll stand up and dance with your arms on each others’ shoulders for an unbelievably awkward middle school style slow-jam!
Challenge One: Cootie Catcher!
What to do:
Cootie Catchers, or sometimes known as paper fortune-tellers, were a staple of the 90s middle-school experience for so many! Try out this fun and nostalgic origami game together with the printable below whenever you are looking for a date night idea!
Included are instructions on how to fold your Cootie Catcher, a pre-filled in option, and one for you to fill in with your own ideas!
Just to remind you, here is how you play:
First, select one person to be Keeper of the Cootie Catcher. The Keeper must hold the Cootie Catcher using both pointer fingers and thumbs.
Next, have the Keeper’s partner select a color. The Keeper must then alternate opening the Cootie Catcher according to the letters in the color selected. For example, B-L-U-E would have the Keeper open the Cootie Catcher four times.
Then, the Keeper’s partner must select a number shown. The Keeper must alternate opening the Cootie Catcher according to the number selected.
Repeat once more.
Finally, have the Keeper’s partner select one final number. The Keepr must then unfold the Cootie Catcher to reveal the result selected.
Boom! There is your date night idea!
Challenge Two: Get Out to Play!
What to do:
You made it through a full day of middle school, but we’re going to go even further back to elementary school because we can’t forget about our favorite subject, RECESS!
Challenge your partner to your favorite outdoor recess games and activities from your childhood! Grab some chalk and draw out a hopscotch board on your sidewalk or driveway, or find a local park and see who can make it all the way across on the monkey bars or jump the highest on the swings!
Then head over to your local consignment sports store and pick up a pair of rollerblades, or a scooter then hit the local trail to take in some killer views of your city or town! Bright colored windbreakers and sweatbands are optional but highly encouraged.
Challenge Three: Dressed to the Nineties!
What to do:
Almost every movie from the 90s has that classic montage where the main characters try on a rotating closet of several different outfits, and now it’s your turn to create your very own 90s fashion show!
For this bonus activity, take turns picking out different 90s inspired outfits for one another. You can find outfit elements either at a thrift shop or by digging through your own closet! Then, grab a disposable camera to snap some pictures and document each new look! Who knows, you might find a rad look that becomes your new fave!
For inspiration, visit Pinterest!
Challenge Four: Share the Love… Notes!
What to do:
Middle schoolers today are missing out on the days of passing notes secretly while your teacher’s back is turned to the chalkboard. This month, use secret love notes as your new way to communicate with one another, not everything has to be as speedy as a text!
We’re talking sappy poems, random thoughts, or secret codes – what you decide to put in each note is all up to you! Just do your best to share a sweet message of love to brighten their day or a silly letter to get your partner to giggle or blush. Once you write it, fold it up and place it in a spot that your partner will find it by surprise! The person with the highest grade from the Awkward Years date-night has to write the first note!
Challenge Five: Quarter Machine Mischief
What to do:
Who remembers hanging out with friends after school? Where was YOUR place? The place you and your friends would always go and hang out. Maybe it was the coffee shop the cool kids went to or the local pizza parlor (which always had the sweet arcade room in the back with the quarter machines).
With your partner, discuss your favorite place to hangout was as a middle schooler. Then, plan a date night there!
Another great thing about being a middle schooler was getting into mischief (although, we know you all were perfect kids)! So, we have a mischievous little game for you both to play on your date!
This game involves your popper and skateboard because, of course, a third great thing about being a middle schooler was spending all your quarters on completely useless items (or so you thought).
First, make sure to bring your popper and your skateboard on your date!
Choose one person to go first (Player One). Sitting across from each other, stare directly into your partner’s eyes. Make sure the center of the table is clear.
Still staring into each other’s eyes, have Player Two set the skateboard next to Player One’s left side and prep the popper on their right side.
Player One must start with both hands underneath the table. As soon as Player Two lets go of the popper, Player One must grab the skateboard with their left hand and catch the popper with their right hand before it lands on the table.
If Player One is successful, they get to choose a Dare for Player Two to do. If they are unsuccessful, Player Two gets to ask Player One a Truth question. Then, switch turns.
Each time you can successfully grab the skateboard and catch the popper, you earn one point. Keep playing until someone reaches 10 points!
Family Date Night Activity: 90s Cartoon Viewing Party!
What to do:
Every generation has its share of awesome TV moments, but we happen to believe the cartoons of the 90s are just a little bit better than all the rest. Which animated masterpieces did you argue with your siblings over the remote to watch on a Saturday morning in your pjs?
The cartoons we watched as a kid are not only funny for kids to experience today, but in some cases are even better when you watch them again as adults! For this bonus activity, put together a 90s themed family cartoon viewing. Many nostalgic shows are streaming such as Rugrats, Doug, Animaniacs, The Wild Thronberrys, Hey Arnold, and so many more! For added fun, grab your favorite sugary cereal to share together!
- Hey Arnold! (1996): Watch it on Hulu
- Rocket Power (1999): Watch it on VRV
- Aaahh!!! Real Monsters (1994): Watch it on Amazon Prime
- The Ren & Stimpy Show (1991): Watch it with NickHits on Amazon
- Rocko’s Modern Life (1993): Watch it on Amazon Prime or with NickHits on Amazon
- Doug (1991): Watch it on Hulu
- Daria (1997): Watch it on Hulu
- Rugrats (1991): Watch it on Hulu
- CatDog (1998): Watch it with NickHits on Amazon
- The Angry Beavers (1997): Watch it on Amazon Prime or with NickHits on Amazon
- Johnny Bravo (1997): Watch it on SlingTV
- Dexter’s Laboratory (1996): Watch it on Amazon Prime
- Ed, Edd n Eddy (1999)
- The Powerpuff Girls (1998): Watch it on Hulu
- Captain Planet and the Planeteers (1990): Watch it on Amazon Prime
- The Wild Thornberrys (1998): Watch it on Amazon Prime
- Recess (1997): Watch it on Disney+
- Batman: The Animated Series (1992): Watch on DC Universe
- Animaniacs (1993): Watch it on Hulu
- Tiny Toon Adventures (1990): Watch in on Hulu
- X-Men (The Animated Series) (1992): Watch it on Amazon Prime
- Spider-Man (The Animated Series) (1994): Watch it on Amazon Prime
- The Magic School Bus (1994): Watch it on Netflix
- Street Sharks (1994): Watch in on Amazon Prime
- Freakazoid! (1995): Watch it on Amazon Prime
- TaleSpin (1990): Watch on Disney+
- Darkwing Duck (1991): Watch it on Disney+
- KaBlam! (1996)
- Pinky and the Brain (1995): Watch it on Amazon Prime
- Pepper Ann (1997)
Date Night Dessert Recipe: Green Slime Pudding
Letters from the Founders:
When we were in middle school, there was one thing we both thought would be so cool: to get slimed on our favorite cartoon television station (you know the one). We also always wanted to be a part of a classic food fight. The ones you always saw in the movies. So, with this month’s dessert recipe and activity, we are making our middle school dream a reality…for you!
<3 Michelle and Tyler
Founders, Crated with Love
- One box of vanilla pudding mix
- Whole milk (according to the pudding mix instructions)
- Water balloons (preferable orange or green)
- A turkey baster
The dessert is the easy part. Just make your pudding according to the instructions on the pudding mix box. Only this time, add some green food coloring until you get that desired “slime” color.
You may want to make two batches. You’ll be “tossing” the first.
Once your slime has been created, choose a day to play Slime or Be Slimed!
Start by filling up three water balloons with your slime. You can use the turkey baster to help you.
Next, go outside and stand one foot away from each other. Take one balloon and toss it to your partner. Each time you catch it, take one step backward. Continue tossing it back and forth until someone gets slimed!
Then, restart a foot away with the second balloon. The person who gets slimed twice loses (or wins depending on how you look at it)!
To show your partner some gratitude for getting slimed, the person who does not get slimed twice must plan a 90s date night for their partner!
*This is also a fun game to play with kids for some crazy fun!
Relationship Focus: Appreciating Growth
It’s been a while since we were in middle school: a period in our lives where we saw growth in various areas of our lives. From first loves, to discovering styles and interests, those were some awkward years for sure. But we’ve grown so much!
Reflecting on that growth can be important to appreciating your journey through life. The same can be said for your relationship. It can be so easy to let time fly by without seeing where you both have come.
Take time to reflect on your relationship and the things you’ve overcome together is not only important to appreciate the past, but it can also help you in the present and for the future.
We may have forgotten certain lessons we’ve learned from earlier on in our relationships, or need a little reminder on those things we’ve experienced. Additionally, learning (or relearning) your past can help you and your partner learn new things about each other.