Valentine’s 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 Burnin’ Love Dragon), and how best to express their feelings.

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It’s OK to feel overwhelmed by it all, to simply visit — or dial 1-800-Flowers, if you’re old school like that (there’s even an app, 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 Valentine’s gift suggestions that will speak louder than words.

Dating for a few weeks

relationship length Valentine Sweets Box

You’re a few dates in and enjoying the spark of a newfound connection. Then, along comes Valentine’s. 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 Wild About You Valentine Sweets Box. It features 3 ounces each of shortbread cookies, gummy hearts, and yogurt-covered pretzels, plus an adorable leopard plush. Best of all: It’s subtle, funny, and cute. Just like the two of you.

Dating for a year

relationship length Heart Shaped Charcuterie and Cheese Tray

The one-year anniversary of your first date and first real Valentine’s 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), and enjoy salami, cheese, and honey from Savannah Bee Company. The snacks are sexy, and the heart-shaped board will serve as a reminder of your love with each use.

Just engaged

relationship length Personalized Pizza Board

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 and rocker so you can make pizzeria-quality pies in your home oven.


relationship length Blooming Love

You’ve already scored lots of gifts from your registry, and now it’s time to revel in your first Valentine’s 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 with a cute — and loving — saying on it. And while you’re in the loving mood, fill up said mug with a fine brew.

Married for 5 years

relationship length Valentines Day Bakery Tray

Half a decade of marriage calls for a platter full of Valentine’s sweets. Go past the typical box of chocolates and score points with an entire bakery tray featuring an array of cakes, including a heart-shaped cheesecake with dark chocolate ganache, and four types of cookies — chocolate chip, two types of shortbread, and raspberry galettes.

Married for 10 years

relationship length Filet Mignon Dinner for Two

Go gourmet to celebrate 10 years of married Valentine’s with a scrumptious filet mignon dinner for two. This three-course meal includes two 6-ounce, bacon-wrapped filets, Gruyère and garlic red mashed potatoes, black truffle and almond green beans, and a chocolate decadence cake for dessert. And did we mention the 36 appetizers it comes with as well? It’s an easy-to-make and sure-to-be memorable meal to celebrate the day of love.

Married for 30 years

relationship length Sweet Treats Wine Pairing Collection

After 30 years of marriage, you have to go big or go home on Valentine’s. The Sweet Treats Wine Pairing Collection is suitably large, with more chocolate goodies than you can shake a cacao bean at. Behold: a chocolate decadence cake, an assortment of chocolate-covered snacks (pretzels, grahams, caramels, cherries), three types of chocolate bars (milk, dark, and salted caramel dark), and a box of chocolate truffles, along with a bottle each of Harry & David Ross Lane Red blend and cabernet sauvignon.

Married for 50 years

relationship length Monthly Flower Subscription

Half a century of marriage calls for a monthly flower subscription. Tell your lifelong love that you care about them with beautiful, vibrant flowers arranged by local florists and delivered right to your door (vase included!). No matter where you live, you and your spouse can enjoy fresh flowers on Valentine’s, and every other holiday to boot!


Richard Martin is a writer, editor, and strategist who specializes in food, drink, travel, and urbanism. He is the co-founder, publisher, and managing editor of Appetito, an online publication about Italian food and drink, and co-author of a series of books called Preserved, which debuted from Hardie Grant Books in the fall of 2023. He is also executive producer on a forthcoming podcast about restaurants starring Marcus Samuelsson and Jonathan Waxman.

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