21 Dates To Try This Season

Whether your summer fling ended and you’re starting to date again or you’re already in a relationship, there are lots of fun, festive things to do between now and Winter. Plus, unlike summer, dating in the Fall makes you naturally get closer to your guy or girl, physically, since it’s starting to get cold. There’s something so romantic about talking a walk through Central Park and looking at the leaves changing color, or “having” to keep each other warm when a brisk wind blows your way. Plus, what better an excuse than “it’s cold out” than finding an Oktoberfest or hotel bar to have some mulled wine or pumpkin beer?

Dating in the Fall is romanticized in movies such as Autumn in New York and Labor Day . Offscreen, too, there are so many activities out there that seduce you into going on fun, Fall dates (which are also great on a budget, as some cost absolutely NOTHING!). Not to mention Fall wardrobes—it’s finally boot weather! (Personally, I think some cool, black, knee-high boots make everyone look stylish, whether it’s intentional or not!) So, pull on those boots, grab some fun fall accessories, and go do the below with your date!

1. Apple Picking

Apple picking is not only fun, but you also feel you accomplish something. (For instance, do you know how to tell when an apple’s ready to pick? Twist it and if it comes off the tree easily, it’s all set to be eaten!) I went apple-picking a few weeks ago while home in the Midwest and a couple bags of apples go far! Not only are they delicious raw, but I’ve made applesauce, apple bread, and am trying an apple pie next.

2. Go On A Walk In The Park or Woods

Yes, spend an afternoon in nature and go check out the trees changing colors, then step on some crunchy leaves (just for fun) and lie down in some for an afternoon nap together.

3. Have A Picnic

While you’re at the apple orchard or in the forest, have a picnic. Autumn weather is perfect to sit (or lie) together under the trees, read a book, and talk.

4. Make Caramel Apples

Anyone can make applesauce, but not caramel apples. With the latter, you can get very creative and even invite friends over to make them with you and your date, or to come eat them afterwards.

5. Pumpkin Patches & Corn Mazes

Go find a pumpkin patch, whether it’s near or far. (Oftentimes, the best ones tend to be outside the city, at least in L.A.) Picking out pumpkins together takes way less time than apple picking, but is still a lot of fun! Usually, there are corn mazes, too, which are great to get lost in together, sneak in some making out, and snap some cool pics.

6. Fall Festivals

Fall festivals are the older sibling to pumpkin patches and have a bunch of festive things for you and your date to do. Aside from picking pumpkins and checking out the corn maze, you can also eat roasted corn, play games and win prizes, go on a hayride, drink hot apple cider, etc.

7. Fall-Themed Events

RISE of the Jack o' Lanterns (in L.A., San Diego, and New York)—with over 5,000 hand-carved, lit up Jack o’Lanterns—is a great Fall, and I’m sure there are similar ones in your town, too! Do some investigating and go find them!

8. Carve Pumpkins

When you get home, carve (or paint and decorate) those pumpkins! Also, make a pumpkin pie for dessert after you make pumpkin seeds! You can also have some friends come over and have a pumpkin-carving party, which I always think are fun! You can have a contest for who carves the best pumpkin, give out parting gifts (i.e., a plastic pumpkin full of candy) to your guests, etc. One of my favorite seeds recipes is here (add paprika for some extra flavor) and this is a great pumpkin pie recipe, even if you’re a first-time baker! (You can use canned pumpkin if you prefer. I won't tell!) You can also make pumpkin or cinnamon ice cream (my fave) to go on top of your pie!

9. Haunted Houses & Hayrides

Whose arms are better to fall into than your date’s when a creepy ghoul jumps out at you at a haunted house or hayride? Exactly! Look up the best haunted houses in your city (sometimes, word-of-mouth ones are better than standard ones, as are neighbors' spooked-out houses). Also, check out haunted hayrides, like the Los Angeles Haunted Hayride, which goes all-out to scare you, yet also is creative and has a new theme each year. This year, they are in New York, also.

10. Go On A Ghost Tour

I did this last year in L.A., a Ghostbusters Tour via Ghoula (Ghost Hunters of Urban Los Angeles). A spook-tacular time! (Sorry, could not resist!)

11. Costume Shopping

Costumes, anyone? Not only is it fun to dress up as an alter ego, but you may also find some outfits to wear on nights other than Halloween!

12. Go To A Drive-In Movie

These are becoming more and more popular again, and are a great way to sit close to your date.

13. Have A Halloween Movie Marathon At Home

If the drive-in’s not showing anything you want to see, host a Halloween movie night at your place—either just for you and your date, or invite some friends.

14. Have A Halloween Party (Even Before Or After Halloween).

I know, Halloween night itself is a popular party night, and you may not want to compete with it. So, you can host a pre-Halloween party (or Day of the Dead party on Nov. 1st): have a contest for best costume, have everyone bring a themed drink or dish, transform your apartment into a haunted house, etc.

15. Oktoberfest

More and more cities are having Oktoberfest celebrations (i.e., an excuse to drink beer and wear Lederhosen while a German band plays in the background). If you don’t have one in your city, you can make your own! Just invite some friends over and have each bring a different Fall beer and Oktoberfest-esque food, like soft, oversized pretzels and brats. (Besides, who DOESN’T look good in Lederhosen?!)

16. Have A Fall-Themed Happy Hour

OK, if you don’t want to go full-out Oktoberfest, you could have a simpler party: Happy Hour. Just make sure you have Fall beers, mulled wine, and hot cider on tap (so to speak).

17. Make A Hearty Dinner

Yes, it's time to dust off that Crock-Pot and make a home-cooked meal to stave off the cold. The Frugal Girls have a great recipe for Dr. Pepper (or Coca-Cola) BBQ Chicken and I like the Pumpkin Turkey Chili recipe from, too.

18. Go To A Fall Sporting Event

There’s NO shortage of football games these days! Find a high school, college, or pro one, bundle up, sit close, and go cheer on your favorite team.

19. Camping

Spend the weekend camping, even just one day or without spending the night! Build a fire, make S’mores, tell each other secrets no one else knows...

20. Go Stargazing

I LOVE doing this (even solo). It is not only romantic, but it's therapeutic and makes you feel like one with the Universe. Plus, you may see a shooting star or two, also. Grab a blanket, a thermos of hot “cider,” and your favorite person, and find a dark, remote area to lie down and look up.

21. Celebrate “Day of the Dead” (“Día de Muertos”) On Nov. 1.

L.A. has a wonderful one at Hollywood Forever Cemetery where people display beautiful, creative altars dedicated to loved ones they’ve lost. You can go with your face painted or get it done there. The more you go celebrate the dead, the more you will be reminded to celebrate life. And that's what it's all about, right?

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Images: Pixabay; Natalia Lusinski; Giphy (5-25)