We’ve heard plenty of reasons why people struggle to find gifts they feel good about giving, but we’re certain anyone can learn to give a great gift with a little encouragement. It is true that certain occasions, likunique giftse Valentine’s Day, can put more pressure on the giver. Depending on your outlook, it’s the gifting holiday that inspires delight, dread, or excitement for Discount Chocolate Day (February 15th, for those marking their calendars). Like it or not, Valentine’s Day gifting says something. Given the incredible market devoted to helping givers find the gift that says exactly what they mean, it seems the conundrum is all too common.

Curious about how to counsel would-be gift givers as the 14th approaches, we turned to Rachel Greenwald, an author, speaker, and dating concierge who has successfully matched hundreds of couples and knows more than a thing or two about nurturing relationships. We asked Rachel about gift-giving etiquette during what can be an emotionally loaded, couple-focused holiday, and she shared her favorite tips for giving gifts that emphasize thoughtfulness over tradition and attention over expense.

Rachel Greenwald, dating concierge and relationship expert

Ideas For Creative Valentine’s Day Gifts

What’s a gift-giver to do when a major gifting holiday falls during the early days of a relationship–are both people obliged to give something special, and how can they possibly do so if they’re still figuring out what makes their recipient tick?

  • Romance isn’t dead, it just needs an update: “I don’t advocate for tradition–it’s cheesy and trite! I’d rather see people skip the flowers and candy and use their imaginations.”
  • On pricy presents: “Don’t make the gift all about money. An expensive gift can feel impersonal, and it’s much more flattering and meaningful to give a gift that shows you’ve been paying attention and listening well.”
  • How to tune in to what makes your partner tick: “It’s about picking up on the little details and quirks of personality. Most people, whether it’s a new relationship or the couple has been together for years, want to know that their partner is listening and aware of their likes and dislikes. Instead of material goods, it can truly be a gift to give someone your attention.”
  • What makes a thoughtful gift regardless of occasion: “Think about how to play up that you’re listening and responding in your relationship. It doesn’t have to be a fancy gift–doing something creative with their favorite treats is a great idea. For instance, think of their go-to movie theater candy. Instead of a dozen roses, maybe you’d surprise them with a ‘bouquet’ of boxes of Milk Duds. It’s a way to create exchanges of thoughtfulness unique to the two of you.”

Cheers, Valentine!

What Makes A Thoughtful Gift For Your Significant Other?

What does thoughtfulness really mean to a gift recipient? Is it determined by tangible and material gifts, or does it all come down to the giver’s actions and attitude?

  • Learn their Love Language: “We often talk about the book The 5 Love Languages by Dr. Gary Chapman, about the 5 ways people give and receive affection: Words of Affirmation, Acts of Service, Receiving Gifts, Quality Time, and Physical Touch. It’s about understanding how someone receives gifts–and feels loved–and realizing that it varies! Two people might speak very different love languages, and that will influence their idea of a thoughtful gift.”
  • Customize a gift as only you can: “Once you figure out someone’s love language, it should be easy to customize your gifts. For instance, if someone’s primary love language is Quality Time, you might surprise them with plans to do something together, just the two of you. You might be different; you might feel most loved when receiving a gift you can open, that someone picked out specifically with you in mind.”

Full Hearts Valentine’s Day Gift

Grand Romantic Gestures Versus Truly Meaningful Gifts

  • You don’t have to go overboard to make a gift special: “When I imagine the typical idea of “grand romantic gestures,” they don’t really make me think of thoughtful gifts. Thinking of the big showy over-the-top displays, like skywriting or flashmobs (editor’s note: or the man who stopped traffic on a Texas freeway for his marriage proposal), they tend to be less special than something simple and personal. I’d say the gestures that pack the most emotional punch are the smallest and most meaningful. They’re the things that show you’ve been paying attention.”
  • Think outside the box–literally: “One proposal I particularly loved that actually could have been a great gift for any other occasion like a birthday or anniversary was by a man who went around with his iPhone taking simple photos for his future wife. He captured pictures that summed up her personality for him–her likes, her favorite candy or most-watched YouTube videos, causes and charities that were important to her and even some of her quirkiest dislikes, like people who crunch their popcorn at the movies–it was just a day in the life of all the things she cared about. He put them in a Shutterfly album for his proposal. It was so special because it could only have been shared by this particular couple, and proved that he knew her best.”

Caramels & Candlelight

There you have it, gifters! There’s still plenty of time to embellish your go-to bouquet and box of truffles for this Valentine’s Day. Take Rachel’s advice to heart and spend a little time considering your recipient–what makes them smile? Where do they love to spend their free time? What one book, movie, song, or food never fails to delight them? Answering even just a few of these questions is a great first step toward finding a special gift for absolutely anyone.

custom gift builder

To learn more about Rachel Greenwald and her books, Have Him At Hello and Find A Husband After 35, visit her website.