5 Fun Fall Dates to Take Yourself On
There is something wonderfully romantic about fall—and absolutely none of that romance has to depend on having someone sitting across the table from you.
You can buy yourself the coffee.
You can take yourself somewhere beautiful.
You can wander through a bookstore for an unreasonable amount of time, drive around looking at leaves, order the dessert, take the pictures, and go home whenever you damn well please.
I think we sometimes treat doing things alone as the backup plan. I'd love to go there, but I don't have anyone to go with. Or, Maybe I'll wait until somebody wants to do it with me.
But what if you stopped waiting?
Taking yourself on a date isn't sad or lonely. It's an opportunity to build a life you genuinely enjoy living—even when nobody else is available to entertain you.
And fall happens to be the perfect season to start.
Here are five inexpensive little autumn dates to take yourself on.
🍂 1. The Coffee + Bookstore Date
Put on an outfit that makes you feel cute, grab your bag, and take yourself out for coffee.
But don't just run through the drive-thru.
Go inside.
Order something you actually like, find a cozy little table, and sit for a while. Bring your journal or a book. People-watch. Write. Read. Stare dramatically out the window while pretending you're the mysterious main character in an indie movie.
Then head to a bookstore.
You don't even have to buy anything.
Wander slowly. Read the backs of books. Browse the poetry section. Look at beautiful art books. Find the strangest title in the store. Make a list of books you'd like to borrow from the library later.
If there's a used bookstore nearby, even better. Give yourself a tiny budget—maybe $5 or $10—and see what treasure you can find.
Little extra: Write a note inside your journal about the day: where you went, what you drank, what you found, and how you felt.
Make a memory out of an ordinary afternoon.
🎃 2. The Pumpkin Patch + Fall Photography Date
Go to a pumpkin patch, farm stand, farmers market, or anywhere else that looks ridiculously autumnal.
Wear your favorite fall outfit.
Walk around slowly.
Look at the pumpkins. Take pictures. Drink cider if it's affordable. Browse whatever little market or shop they have. Enjoy the ridiculous number of decorative gourds.
And yes, take pictures of yourself too.
Prop your phone against something. Use the timer. Take the cheesy pumpkin picture.
You don't need another person standing beside you for your life to be worth documenting.
If pumpkin patches near you charge admission, make your own version. Visit a farm stand, farmers market, park, or even a garden center with a beautiful fall display.
Little extra: Buy one small pumpkin and take it home as your souvenir. Put the date on the bottom.
Now it's not just a pumpkin.
It's the pumpkin from that lovely afternoon you took yourself somewhere.
🍁 3. The Fall Wandering Date
This one is almost completely free.
Pick somewhere pretty and wander.
Go to a park, walking trail, historic neighborhood, little downtown area, cemetery, lake, college campus, or country road.
The only rule is that you're not rushing.
Bring your headphones and make yourself a fall playlist beforehand—or leave them at home and listen to what's around you.
Take pictures of interesting things.
Collect pretty leaves.
Sit on a bench.
Find the reddest tree.
Look at old houses.
Watch squirrels frantically conducting their autumn business.
Stop somewhere and drink coffee from a thermos.
Let yourself have absolutely nowhere else you're supposed to be for an hour.
Little extra: Turn it into an artist date. Photograph colors, textures, doors, shadows, leaves and little details that could inspire future artwork or journal pages.
You aren't just going for a walk.
You're collecting inspiration.
🥧 4. The Thrift Store + Homemade Dinner Date
Give yourself a tiny amount of spending money—$5, $10, whatever works—and go treasure hunting.
Visit your favorite thrift store and take your time.
Look through the books.
Dig through the mugs.
Try on something ridiculous.
Look at the abandoned artwork and wonder who owned it before you.
Search for something that feels perfectly autumnal: an old hardcover book, vintage scarf, little basket, candleholder, cardigan, mug, picture frame, or strange little object that speaks to you.
The goal isn't really shopping.
It's treasure hunting.
Then go home and make yourself dinner.
It doesn't have to be fancy. Make soup and grilled cheese. Pasta. Chili. Baked potatoes. Breakfast for dinner.
Put your food on a real plate.
Light a candle.
Turn on music.
Pour your drink into a pretty glass.
Then watch a cozy fall movie while you eat.
Little extra: Use whatever you found at the thrift store that same evening. Drink from the mug. Read the book. Wear the sweater. Put the flowers in the vase.
Your $3 treasure becomes part of the date.
🌙 5. The Moonlight Artist Date
This one might be my favorite.
Stay home.
But make staying home intentional.
Take a shower or bubble bath. Put on your favorite pajamas. Make coffee, tea, cocoa, or whatever little drink makes you happy.
Turn off the overhead lights.
Light candles or turn on fairy lights.
Put on music.
Then get out your art supplies.
Paint.
Collage.
Color.
Write poetry.
Work in your art journal.
Make something terrible.
Make something beautiful.
Make something you don't intend to show anyone.
Later, step outside for a few minutes and look at the moon.
Really look at it.
Notice the temperature. The smell of the air. The sound of everything settling down for the night.
Then come back inside, curl up somewhere comfortable, and read or watch something you love.
No scrolling.
No waiting for messages.
No wondering what everyone else is doing.
Just you, your little home, your creativity, and an autumn night.
🍂 Learning to Romance Your Own Life
There's something powerful about realizing you don't need to wait for somebody else to begin enjoying your life.
You don't need a partner to visit the bookstore.
You don't need a friend to go see the leaves.
You don't need somebody sitting across from you before you're allowed to order coffee and stay awhile.
And you certainly don't need a special occasion to light the candles and use the pretty dishes.
Take yourself.
Buy yourself the $4 coffee.
Wear the cute outfit.
Photograph the day.
Bring home a leaf.
Write about it in your journal.
Create little traditions that belong entirely to you.
Being comfortable alone doesn't mean you don't love other people or enjoy their company. It simply means your happiness isn't sitting somewhere outside of you, waiting for another person to arrive.
There is a whole life happening right now.
And sometimes the best person to explore it with is yourself.
So pick a day, put on your favorite sweater, and ask yourself the same question you'd ask someone you adored:
Where would you like to go today?
