The cutest fall first date ideas

You already know about fall fun: homecoming, new classes, pumpkin spice, coziness, football games, changing leaves and the like. But maybe you've met a special someone in biology, are on the lookout for a hoco date or ran into someone cute on varsity. Tbh, fall is *the* season of new crushes—and the perfect time for first dates! 

You'll need some creative fall date ideas to impress your crush that will *actually* help you two for a connection. That's where we come in...

1. Halloween movie and baking night

Grab some ready-to-bake Halloween cookies and turn on a classic movie. There are so many ways to spice up the classic pumpkin cookies—you can bake them on top of chocolate chip cookie dough or all together as a cake. Halloween classics like Hocus Pocus or The Nightmare Before Christmas make a super spooky backdrop.

@recipes No “tricks” with these cookies! Just a sweet ✨treat✨! 🤗🧡🍪 Are you gonna recreate these 2 Layer Halloween Cookies this fall season?🤩 #pillsburycookies #chocolatechipcookies #halloween #fall #season #dessert #recipes ♬ original sound - Viral Recipes

@sweetly.jamie Pumpkin Print Cookie Cake! A sharable festive dessert for fall/halloween!🎃 #easydessert #falldessert #halloweendesserts #cookiecake ♬ This Is How We Do - Katy Perry

2. Fire pit and s'mores night

Cuddling by the fire is a nostalgic and cozy way to bond with your crush. For peak connection, bring a card game or ask each other We're Not Really Strangers-inspired questions. This will help spark amazing convos so you can learn more about your boo. Bonus points if you bring apple cider to keep the fall vibes going. 

3. Farmers market run

What better way to get to know your crush than by visiting your neighborhood farmers market? You could grab coffee, fresh fruit, pastries or even a full breakfast in the crisp, cool air. This date's giving wholesome, hometown Hallmark movie vibes.

4. Coffee shop and park

Now's the perfect time to find out your crush's favorite fall coffee! This is a great casual option if you need more time getting comfortable with each other. Picking a local spot and heading to a park for a mini coffee picnic will also score you *indie* points over a Starbucks or Dunkin'.

Photo by Asal Lotfi on Unsplash

5. Sweater swap 

Is your love language gift-giving? While a first date might not be *quite* the time yet for a sentimental gift exchange, this date idea might be the closest it gets.

Head to the mall and set up a sweater challenge: Each of you has to try on what your date selected for you! Maybe you'll pick out a hilarious sweater, something genuinely cute or a sweater that pushes them out of their comfort zone. This adventure will likely produce lots of laughs and something to remember each other by 'til the second date.


6. Pumpkin painting 

Tbh, pumpkin carving is the fall equivalent of ordering chicken wings with BBQ sauce on the first dinner date—kinda messy and kinda gross. That's why we heart pumpkin painting.

Work together to paint one pumpkin because it will challenge you to complete a creative task together and collaborate (that's great for budding couples, BTW). Compatibility test: check. Romantic: check. Fall vibes: check. 


7. Fall farm outing 

Schedule: They pick you up to drive to the apple orchard, you sing along to "Starlight (Taylor's Version)" in the passenger seat, you arrive, you immediately get apple cider doughnuts, you talk and get to know each other while you eat, you pick apples from the trees together, you snap a pic showing off your basket of apples, they drive you home, you talk the whole ride and maybe you get a kiss goodbye. Isn't that just the perfect fall date? 


8. Ballet date 

Feeling fancy? Go to the ballet together. Lots of companies put on their holiday ballet productions during November, so check your local theater's lineup. If you're the kind of girl that's looking for a formal occasion as an excuse to go glam, this is your chance to! And if your idea of romance is straight from the books (picture: dresses, ballrooms and dancing), then this might be your modern-day solution. 


Follow @girlslifemag on Instagram for more fall inspo!

Need some second-date ideas? We've got you covered:
💞 Alphabet date ideas you need to try 
💞 9 out-of-the-box date ideas
💞 10 low-key date ideas

Slider image: @itsnataliecass
Top image: @halleeee.sand


by Madelyn Willoughby and Kayla Conroy | 10/7/2023