In “Ultimate Gift Guide, we’re bringing you all the best advice on gifting, whether you need something to share for the holidays, bring to an event, or gift just because.

Valentine’s Day is such a wonderful celebration of love and romance, yet it is also one of the most complicated holidays for gift giving. Lovers young and old are faced with all sorts of calculations when choosing a gift, such as how long they’ve been dating, whether to go traditional (a dozen roses or a box of chocolates) or more creative and quirky (like the Quill You Be Mine Plush Porcupine), and how best to express their feelings.

It’s OK to feel overwhelmed by it all, to simply visit 1-800-Flowers.com — or call 1-800-Flowers, if you’re old school like that (there’s even an app now, too!) — choose a bouquet, and call it a day. But for those who want to find that perfect token of affection, a way to say “I love you” that has added meaning, we put together a guide of gifts based on the length of the relationship. Whether you’re three dates in or celebrating a lifetime together, here are eight suggestions that will speak louder than words.

A photo of relationship length with a platter full of chocolate covered pretzels.

Dating for a few weeks

You’re a few dates in and enjoying the spark of a newfound connection. Then, along comes Valentine’s Day. So much pressure! You need to find a gift that says, “I’m liking where this is heading” without appearing too clingy or needy. In other words, play it cool with the We Go Together Like Chocolate and Pretzels Gift Box. It features 10 ounces of Belgian milk, dark, and white chocolate-covered pretzel twists and other colorful chocolate-dipped treats. Best of all: It’s subtle, funny, and cute. Just like you.

A photo of relationship length with a heart shaped charcuterie board supporting a wedge of cheese, some salami and crackers with the same ingredients in bowls surrounding it.

Dating for a year

The one-year anniversary of your first date and your first real Valentine’s Day together are of near-equal importance. For the latter occasion, you need a gift that’s more about romance and togetherness, such as a heart-shaped charcuterie and cheese tray. Curl up by the fire, open a bottle of wine (or a trio from California ), and enjoy cheese, salami, and flatbread bites. The snacks are sexy, and the heart-shaped board will serve as a reminder of your love with each use.

A photo of relationship length with a personalized pizza board.

Just engaged

Get ready to start nesting, filling your soon-to-be marital home with memorable items, such as a personalized pizza board. The pizza peel can be customized with three lines of text in three font options, so craft a message that showcases your love for each other — and your favorite topping! (“Olive juice” anyone?) The set includes a pizza crisper so you can make pizzeria-quality pies in your home oven.

A photo of relationship length with a personalized mug that says love on it.

Newlyweds

You’ve already scored lots of gifts from your registry, and now it’s time to revel in your first Valentine’s Day as a married couple. Don’t overthink it. Make sure you at least pick up a dozen red roses. The savvy spouse won’t stop there, though: Add an oversized 30-ounce coffee mug featuring your love’s name written into the word “LOVE.”

A photo of relationship length with a board full of different kinds of cookies and chocolate covered nuts

Married for 5 years

Half a decade of marriage calls for a platter full of Valentine’s Day sweets. Go past the typical box of chocolates and score points with a dessert charcuterie board featuring an array of colorful and heart-shaped cookies, gummy candies, chocolates, and more. You’ll be amazed at how sweet the “more” treats are.

A photo of relationship length with a plate full of four small lobster pot pies and two small chocolate cakes in ramekins next to them.

Married for 10 years

Go gourmet to celebrate 10 years of married Valentine’s Days with a tasty lobster pot pie dinner for two. This three-course meal includes two seven-ounce lobster pot pies, two four-ounce crab quattro formaggio on the half shell, and two chocolate molten dulce de leche soufflés for dessert. It’s an easy-to-make and sure-to-be memorable meal to celebrate the day of love.

A photo of relationship length with a box full of pears, chocolate, and Moose Munch next to a bottle of wine and several bowls of the same ingredients.

Married for 30 years

After 30 years of marriage, you have to go big or go home on Valentine’s Day. The Grand Valentine’s Day Gift Box with Wine is suitably large, with an eye-popping array of treats that includes pears, Moose Munch popcorn, chocolate candies, cookies, stickers (yes, stickers), and a bottle of Harry & David 2019 Royal Crest Red blend wine. There’s even a canvas tote, in case you want to take your Valentine’s Day celebration on the road.

A photo of relationship length with a plate full of whole and cut fruit.

Married for 50 years

Half a century of marriage calls for a subscription to the organic fruit of the month club. Tell your lifelong love that you care about them with healthy, nutritious fruit grown organically, including HoneyBells (February), pineapples (April), strawberries (May), plums (September), and more. No matter where you live, you and your spouse can enjoy fresh organic fruit on Valentine’s Day, and every other holiday to boot!

Author

Richard Martin is a writer, editor, and strategist who specializes in food, drink, travel, and urbanism. He is the editorial director of Marcus Entertainment, a new media company from Marcus Lemonis, and the co-author of a forthcoming series of books called Preserved, debuting from Hardie Grant Books in fall 2023. He is also executive producer on a forthcoming podcast about restaurants, starring Marcus Samuelsson and Jonathan Waxman.

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