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Valentine’s Day date ideas for every kind of person

For some, Valentine’s Day is a time for romance, roses, and grand gestures; for others, it’s a day like any other—or an occasion frankly best forgotten. No matter how you feel about this much-debated holiday, chances are you’ll find yourself considering how to spend it. 

That’s why this week’s Ask Anna is dedicated to date ideas. Whether you embrace the love or not, I’ve conjured up a variety of Valentine’s dates to suit every type of person and every kind of budget—from enthusiasts to haters, from the budget-conscious to the ballers, and beyond. 

Valentine’s Day Enthusiasts

For those who have been waiting all year to unleash their inner Cupid, why not go all out with a themed scavenger hunt? Leave clues around your city—or just within your home—that lead your beloved to a series of romantic locations (such as your first date, first kiss, anniversary locales, or any place that’s meaningful). You could also make the locales part of the date—a dessert place, a romantic stroll, a massage, etc.

Extra credit: Include a small gift (or poem or a list of your favorite things about them) at each spot.

Alternatively, bring the fine dining experience into your own kitchen with a private dinner. Whether you opt to hire a professional chef for the evening (yes, it’s a thing! Google “personal chefs near me.”) or choose to cook a special meal together, the intimate setting can make for a memorable night.

Extra credit:  Set the whole mood with a nice table cloth, lighting, music, pleasing scents, and your date’s favorite beverages.

Valentine’s Day Haters

Not a fan of all the mushy stuff? That’s perfectly fine! Throw an Anti-Valentine’s Day party. Invite friends over for a night of games, death metal music, and revelry, where the only rule is “no romance allowed.”

Or, if there’s a smash room or place to break things safely near you, consider scheduling an hour with friends to beat the crap out of something. Or, for the lo-fi version: Buy a cheap piñata.

Or you can settle in for a dark comedy movie marathon. Choose a lineup of films that satirize, twist, or downright eschew traditional romance narratives.

Extra credit: While the lovebirds are out there naming stars after their beloveds, you could go the opposite route and name a cockroach (or vegetable or rodent) after your ex. For as little as $5, the San Antonio Zoo will do this and feed the vermin to a zoo animal.

The More the Merrier

Whether you’re poly, prefer to double or triple date, or have a tight-knit friend group, arranging a Valentine’s Day group date can be a fun and unique way to celebrate. You can make it themed, like an homage to friendship, or simply enjoy together. Here are few group date ideas:

Cheap thrills: Head to a dollar store (or a big-box store like Target) and find cheap gifts for everyone in your party. Set whatever rules you want—No more than $5? Something soft? One gift for every sense?—then open them together over coffee.

Host a cookie swap or baking party. Decide on a few desserts to make together, or do it potluck-style and have each person bring a sweet of choice, then come together to enjoy a feast. You could have a theme like “Great British Bake-Off Attempts” or favorites from childhood.

Extra credit: You could also do this with any food or beverage of choice—wine, beer, sake, sparkling water, appetizers, and so on. Each person or couple could bring a bottle or dish for a tasting.

Host a Valentine’s Day themed trivia night where every question is about love or Valentine’s Day. This could be about famous literary couples, historical traditions, or, for extra fun, your own group.

Have a DIY Valentine’s Day card-making party. Each person can bring different supplies, and you can compete to see who can create the most beautiful or creative card.

Extra credit: To make it more challenging (and eco-friendly), you’re not allowed to buy any supplies, but can only use materials you already have around the house.

On a Shoestring Budget

Money shouldn’t be a hindrance to celebration. If it’s not freezing, a simple picnic in the park, with snacks and hot beverages, can be a charming way to spend the day. If it is freezing, create a picnic in your living room, with pillows, blankets, bubbly, and your favorite foods.

If you’re looking for something more nocturnal, try stargazing. Grab a blanket, a thermos of hot cocoa (spiked or not), and gaze at the stars together—whether on the roof, or somewhere nature-y that gives you a better view.

Extra credit: Peruse the local papers or community websites to find low-cost events, such as concerts in the park, art openings (that often have free wine), community theater previews, high school or college sporting events, or lectures and book readings.

The Swanky Affectionados

For those with skrilla to spare, go full baller with a helicopter, private plane, or balloon ride over your city. 

Or, splurge on a decadent spa day or a night at the upscale theater (opera, ballet, or symphony). Bonus points: Buy their outfit for the event as well and hire a car to chauffeur you around. Preening, pampering, and cultural enrichment can make for a grand gesture that’ll be remembered long after the chocolates have been eaten.

Extra credit: None needed. You took them on a helicopter! But okay, go nuts and hire a private chef, too. (See above.)

Homebodies United

If you can’t leave the house (or don’t want to), create your own themed dinner and movie night where you choose a country and make a traditional dish from that place, then watch a movie or listen to music from there as well. An example of this would be an Italian movie and homemade pasta or sushi and an anime film.

Write or dream together: Collaborate on writing a short story, poem, or even plans for the future, like a couples bucket list or future vacations. This activity can reveal new facets of your creativity and thoughts. Plus, research shows that simply looking at travel websites gives us the happiness boost  as actually traveling, minus the food poisoning or flight delays.

Engage in a friendly cook-off challenge. Pick out a recipe that neither of you have tried and cook your way to a new tradition. Or, pick one recipe and have one person do the main, and the other do the sides or dessert.

Extra credit: Find a DIY project to tackle together. Whether it’s organizing a junk drawer or painting the bathroom or finally hanging up the kids’ school photos, it’s a productive and fun way to spend time together. Be sure to reward yourself during and after.

Adventurous and Outdoorsy Types

If the weather agrees, plan a hiking trip that culminates in a stunning view, ideally coordinated with the setting sun. There’s nothing quite like a shared vista to inspire feelings of awe—and love. If it’s cold or snowy, there’s always ice skating, wintry walks, indoor botanical gardens, exploring a night market, or sledding.

Water lovers might enjoy an afternoon of kayak or paddleboard rental for a duo adventure out on a lake or bay, adding a splash of sportive engagement to the day’s romance. 

Extra credit: If there’s bioluminescence anywhere near you, consider splurging for this memorable experience.

Long-Distance Lovers

Thanks to technology, distance doesn’t have to dampen Valentine’s Day. Plan a virtual date night with a food or beverage kit that you can make together (while apart) over video call. Or, with some creativity, you can try many of the other dates suggested here.

Or send a surprise care package to your partner filled with all their favorite goodies (snacks, cozy socks, a music playlist, a book of poetry, etc.)—a personal touch that says “distance means so little when someone means so much.”

Extra credit: Do both.

First Valentine’s Together

Make memories by doing something meaningful or brand new to both of you—like visiting a quirky local museum or attraction or visiting a “makeout spot” (most towns have one and you can often find out where online). You could also try out a new-to-you activity like a dancing, pottery, or archery class. Fill your day with a series of “firsts” to make it unforgettable.

Extra credit: Hire a photographer (like Shoott) to do a couple’s photo shoot with you while you’re on your date.

Flying Solo

Who says you need to be partnered up to treat yourself right? Dream up your perfect date and then make it happen. Is there a restaurant you’ve been wanting to try? A hobby you want to learn? A super cheesy movie that not even your friends want to watch? TREAT YOURSELF.

Or, volunteer at an animal shelter or an old folks home and spend some time with those who need an ear or a cuddle (respectively). 

Extra credit: Take some advice from Miley Cyrus and send yourself flowers or a boozequet (a boozy bouquet).

Valentine’s Day doesn’t have to be a one-size-fits-all affair. It’s a flexible occasion that can be shaped and celebrated in countless ways. Remember, the idea behind the day is to celebrate love in all its forms, and that can be with your partner, friends, family, or even yourself. So, don’t feel boxed in by tradition—make this V-Day authentically yours.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books!

This column originally appeared on The Chicago Tribune.

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