Are Valentines Gift Guides Silly?
9e614e3e0633cb3a8720eb526d349cee original

Gentlemen, no one wants to be the bearer of bad news, but we have reached critical mass regarding heart-shaped boxes of chocolate and cellophane-wrapped roses. And the little teddy bears holding those tiny heart pillows? Their population is surging to unprecedented levels as of late. Also on the rise are those lists known as Gift Guides, something editors whip up to get you to part with your well-earned cash (although if that’s what you’re looking for, no judgement).

There’s no question as to why this is all happening. We all know how to read a calendar. February 14th will soon be here, and despite the uptick in these shiny, disposable trinkets, the message they send to the recipient remains the same, and is as loud and blaring as an air horn at half time: Sorry honey, I was too busy. I have no imagination. I just don’t really know what to get for Valentine’s Day.

The key to being a great gift-giver is to add that subtle personal touch. It comes down to three things: knowledge, nuance, and timing. Take what you already know, add a special twist that makes it personal, and execute like the deep-down romantic mastermind you know you are. Or have the potential to be. Either way, read on.


A solid gifting strategy is to pick a beloved hobby and expand upon it. If it’s something you love doing together, hey, even better. For example, let’s say you like to imbibe some adult beverages from time to time. A cocktail recipe book, or a special set of tumblers can set the stage. Mike, who lives in San Francisco, knew his girlfriend loved rum drinks, especially from a famous local tiki bar they had once visited - Smuggler’s Cove. Mike bought her a recipe book published by the bar (followed by a surprise table for two and a round of mai tais) and it was a big hit. Pro tip: if you’re giving multiple gifts that go together, always give the smaller one first. For example, lead with an exceptional set of wine glasses, and finish with - surprise! - a handsome bottle of a nice red.

Stacy, a recruiter in Philadelphia, actually favors more traditional gifts, like flowers. Stacy recalls a time in the early stages of her relationship with her now-husband, Brad, where he really nailed it. “Brad had been to my office, which at the time was just one big open floor plan. I was working long hours so he had a bouquet delivered to my work instead of my home.” The feeling Stacy had when she saw the receptionist from across the room walking past all of her co-workers on the way to her desk to plunk down the impressive bouquet has stuck with her. “Heads were turning,” Stacy recalls. It also put the kibosh on a couple of flirty co-workers who didn’t know she had a boyfriend. “It pretty much shut them up,” Stacy says. “It said: I’m taken...and proud of it!”


That very same Valentine’s Day, Stacy’s co-worker Adam didn’t fare so well. Adam, fresh out of college, had been on just a couple of dates with a new girl. He was into her, but wanted to send her something simple for Valentine’s Day, just to let her know she was on his mind. Adam had a dozen roses delivered to her office, and excitedly told his co-workers all about it. “Adam was so proud of himself,” Stacy recalls. Then Adam added in the detail of the color of said roses: yellow. “Rookie mistake,” says Stacy, as yellow roses are a symbol of friendship, and nothing beyond that. Adam’s face fell as his co-workers clued him in on this important detail. Needless to say, it was not the outcome Adam had hoped for. He was coming from a good place, but didn’t really know what he was getting into, and it ended up sending the wrong message.

Rachel lives in Cambridge. She’s an entomologist, and received a grant to study insects at one of the top schools in the country. Her favorite subject of all is dragonflies, and all her friends know this for a fact. Rachel even has a tiny pair of gold dragonfly earrings. Come Valentine’s Day, her boyfriend of three years got her a framed print of all the different species of...butterflies. Oof. Talk about missing the mark. Or maybe just not taking the time to understand the subtleties of your loved one’s favorite subject.


Jordan and Chris live in Seattle and have been together since college. Over time, it’s become a tradition for them to go to a few Mariners games together every summer. Giving each other Mariners tickets for birthdays and holidays had become the norm over the years. But Chris threw Jordan a serious curve ball last Valentine’s Day. “I like Rihanna, but Jordan is her number one fan,” Chris explains. “I got an envelope and decorated it with baseball stickers and Mariners colors. The look on Jordan’s face when he opened the envelope and saw what the tickets were really for was priceless. And then we saw Rihanna together later in the year. It was like it came with a built-in date.”

So, let’s review.

  • Mike knew his girlfriend’s tastes, and planned their special night accordingly.
  • Brad was clued in on Stacy’s preferences (and that she enjoyed having her moment in the spotlight) and gave that to her, even though he couldn’t be there in person.
  • Keeping track of little things is worth it. We know a guy who jots down a few words in a note-taking app on his phone when the moment strikes him. It allows him to keep a running list of his loved one’s tastes and preferences that can be called upon later. You don’t want to be the one giving a butterfly present to a dragonfly girl, right?
  • Chris took a well-worn, expected scenario and turned it on its head by putting Rihanna tickets in a Mariners-themed envelope. The element of surprise isn’t always necessary, but the payoff can be huge.

Ah, romance. It’s all around us this time of year. Something else saturating our lives at the moment are messages telling us what the typical gifts are that we’re “supposed” to buy for Valentine’s Day. We’ve never been big fans of convention, and chances are you aren’t either. By all means, show your love, because your special someone is exactly that: special. Not generic, not average, and definitely not basic, as the kids say. So why buy a Valentine’s Day present that was blindly picked by a stranger, or that you got at CVS on your way to dinner? Come on dude, you can do better. After all, matters of the heart don’t just happen by accident. It also takes a little bit of brainpower.

Got a gift-giving story? Tell us about it: [email protected]