Valentine’s Day is one of the most popular occasions for gifting chocolate. And, yet, many people pay surprising little attention to what they buy. If it’s in a red, heart-shaped box, and it costs more than $20 it has to be good, right?

Maybe not? Where did you get that box and how much thought did you put into purchasing it? Was it a last minute purchase from a drug store on your way to dinner – because it slipped your mind? If so, it’s not likely to deliver the message or impact you want.

Chocolate is known for its ability to forge strong emotional connections and memories and the best way to gift chocolate, for Valentine’s Day or any other day, is to recognize that and work with it. A nice two-piece box that you thought about can say a lot more than the boxed assortment you picked up in a chain store - even if it’s a chocolate chain store.

Buying chocolate for someone you know

The key point to remember is that the gift is about them, it’s not about you. Never buy something you know the recipient does not like.

Buying a boxed assortment says that you punted on thinking; the choice was more about convenience or quantity or price, not quality. When you walk into the store, go to the case (no case? you are not in the right store), and tell the person behind the counter that you’re buying chocolate for a gift - and that the recipient really likes the following flavors. Then ask what they have that matches what you know the recipient likes. If there are five that might work and the choice is either a four-piece box or a nine-piece box, go for four.

Take your time deciding which four and remember the reasons why you chose the ones you did. Then, when you present the box, tell the story about buying it … being presented with so many options and having to make choices and then connecting your reasons for purchasing with something you know, like, or admire about the person … or connect it to a shared experience.

Or maybe the person you’re gifting to is really adventurous when it comes to eating. A selection that is composed of unusual flavors (which you might not like) could be a big hit as it would acknowledge their desire to explore new flavor combinations.

What you’re doing by selecting a gift this way is showing that you thought about the process and the person who the gift is for - while also revealing what it is about the recipient that either attracts you or that you admire, and you’re looking to establish, or reinforce, a strong emotional connection.

That four-piece box selected with care will get you many more props than a larger boxed assortment – even from the same store — unless, of course, you know that the recipient is a fan of a particular brand of boxed assortment chocolates from childhood. Then by all means gift one of those. What’s important is that the gift reflects your understanding of what the recipient likes and values.

Buying chocolate for someone you don’t know

This advice is mostly for selecting chocolate for someone you’d like to get to know better, and it’s basically the inverse of the advice for buying for someone else.

Approach the case and ask the person behind the counter if they have flavors that are what you like, or that you have a special connection with – maybe something from childhood. Select those and be prepared to tell stories about what the pieces mean to you: why you selected them. By sharing the stories behind the chocolate you tell the recipient a lot about yourself. Hopefully in a way that is totally endearing. This is what you want.

For example, growing up in Southern California, we would gift my mother a box of See’s Victoria English Toffee – a childhood favorite of hers from growing up in LA in the 1920s and 1930s – on Christmas Eve. If I were gifting chocolate to someone I wanted to get to know better I would definitely include a piece of toffee covered in dark chocolate and sprinkled with roasted almond pieces and tell a story about the ceremony around gifting the box, my mother unwrapping it, and then sharing the box around so everyone got a piece.

Still don’t know what to gift?

If the gift is for someone you are romantically involved with (or want to declare those intentions) - you simply cannot go wrong by selecting nicely decorated heart-shaped pieces with a filling flavored with passionfruit. Two - one for each of you. And you’ll find that a nice rosé or Prosecco is a tasty pairing.

A great technique when you’re gifting for a boss or other colleague is to go into the store and ask the person behind the case what the most popular items are - what sells best is also often the freshest. You can ask them their favorites, as well, and I sometimes ask to be pointed out a selection that they think represents the best work they do. Pick an unusual flavor - something you might never buy on your own but that is really popular. You could even buy one for yourself (packed separately) and then suggest you both eat the piece at the same time and figure out whether you like it or not.

And in closing ...

Whatever you do, make it fun. If it involves chocolate and you are not having fun, you’re doing it wrong.