Better Gift-Giving: A Man's Guide

If you think you’re already a gift-giving ninja, you can stop reading right now.

But if you’re like the rest of us guys, you might feel like every birthday or anniversary for your significant other is a mid-term that you always end up cramming for, and usually just barely pass.

How many times have you found yourself racking your brain for ideas just 24 hours before some special date? Or desperately running around from store to store to find something, ANYTHING, that speaks to you and says “I am the super-thoughtful gift she’s going to love.”

Or the worst part: when you end up just settling, and “phoning it in”–just getting her something safe like jewelry or chocolates, when deep down you know you could probably do better. You know you could find something more personal, more special that shows you really thought about her.

Why is it that finding good gifts is so hard for guys?

It’s not because we’re not thoughtful (at least usually). The truth is, we’re just uneducated in the “gifting arts.” Fortunately, gift-giving is a skill that can be learned and honed like any other craft. Here are seven strategies for how to improve your gift-giving chops:

1. Do Your Homework

When you’re getting a gift, remember that it’s all about her. It’s okay to do some research at stores to find some ideas. But if you really want to be successful, do your homework first. Scientist Louis Pasteur famously said that, “Chance favors the prepared mind.” Even if you’ve been together a few years, there are probably all kinds of little details about her that you haven’t noticed and might help your gift search.

Take an inventory of everything you know about her, from the basics to the most obscure: What’s her favorite color? What’s her favorite flower? Know her birthstone. Know her ring sizes (for ALL her fingers–what if you see a totally awesome thumb ring that you think she’d love?).

What kinds of things does she like to do? Is she really active? Is she a bookworm? Even though some of it may seem obvious, sometimes just going over these little details can inspire you to think of an idea. At the very least, it will better prepare you to find recognize that great gift when you’re out searching.

2. Pay Attention

Sometimes great ideas will present themselves to you if you just keep your eyes and ears open. In The Gift-Giving Handbook for the Inept Man, the author notes that “Observation is the most important trait a gift giver can possess.” If you observe her closely, she’s probably giving you loads of potential clues for gifts.

Some women are actually pretty crafty about this–they knowingly plant seeds about stuff they want. But even if not, you can still get ideas from observing. Watch her as she points out things in magazines. Watch her when you’re shopping together. What is she drawn to? What things has she commented on? “Hmmm..that’s kind of cute…”

3. Ask for Help

Of course you can always just ask her for ideas, or do something like check her Amazon wishlist, if she has one. The only problem is, (a) that’s kind of weak, and (b) some of the best gift ideas may not have even occurred to her. Another option is to enlist the help of her friends. Ask them for some ideas–get their perspective.

Or if you want to really do it right, invite one of her friends out shopping with you–have her help pick some things out. It’ll end up being a win-win: you can spend the afternoon together, grab lunch and catch up. And you’ll get some great ideas you probably wouldn’t have thought of yourself.

4. Think of Gift-Giving as a Year-round Endeavor

Let’s face it, most of the important dates in your life aren’t a surprise. Your significant other’s birthday. Valentine’s day. Your anniversary. Christmas. They’re the same time every year. So why do they always seem to catch us by surprise? Why are we always “cramming” at the last-minute? There’s no reason you can’t always be on the lookout for ideas.

Start an on-going list of potential gifts in a notebook or (if you want a more 21st century option) a note-taking app like Evernote. Start a “gift closet” or gift cupboard or drawer, where you can store stuff you come across. Think of it as a savings account for your gifts.

It makes a lot of sense: with a savings account you don’t wait until you need money to start putting money in; ideally, you put money away a little at a time when you can. Then, when actually need it, it’s there for you.

Along the same line, there’s no reason you can’t stockpile cool/touching greeting cards. At first it might seem impersonal to “buy in bulk” ahead of time, but ironically it probably has the opposite effect. By finding cool gifts and cards without an impending deadline, you end up getting stuff that’s way more thoughtful than when you’re down the wire and you just have to grab something.

5. Learn to Edit

Aside from the other benefits we talked about earlier, another benefit of thinking of gift-giving as a year-round endeavor is that it gives you the luxury of being able to edit. There’s a great quote, which I’m going to botch, but it goes something like this: one of the main differences between a great photographer and a regular person taking pictures is that a great photographer takes 500 pictures to end up with 1 or 2 amazing photos, while the amateur photographer takes only a handful of pictures and is disappointed not to have 1 or 2 amazing pictures among the few they’ve taken.

Now, I’m not saying that you’ll need to 500 gifts to find one or two good ones. But when you search for gifts earlier and pick up a few things along the way, it gives you the opportunity to re-evaluate at the end. Then you can select the “best of the best” to actually give to her.

Knowing that you’re planning to edit later will also help you cast a wider net initially, and you’ll agonize less over trying to find the absolute perfect thing right from the start. As long as you keep your receipts (or consider gifting to someone else), you can’t lose with this approach.

6. Always Look for Ways to Personalize

Remember that a gift should be all about her. Something that shows you thought of her. If it seem like you’re getting her the same gift you would have gotten your ex-girlfriend, the card might as well read “insert name here.” Even if you get something fairly conventional, it’s not difficult to add a personal touch.

A few years ago I wanted to mount a TV in my wall, so I got help from a friend who was pretty handy and he helped me cut a whole in the wall and run the wires behind, etc. When it came time to actually mount the TV to the studs, my friend started hack-sawing off part of the metal mount that had come with the TV. I was pretty startled. I’ll always remember what he said: “You know, everything’s always just a starter kit. You’ve always gotta customize.” This couldn’t be more true with gifts.

Just because you’ve found the perfect gift doesn’t mean your job is done–look for a way to make it more personal, even if it’s something you’ve purchased. It goes without saying that if you buy her a book, you MUST inscribe it. There’s nothing sweeter than her pulling the book off the shelf years later and reading the note you wrote her when she got it. Or instead of a regular box of chocolates, get her some monogrammed chocolates. Did you know you can even get personalized M&M’s now? These days, with the power of the internets, you can personalize just about anything for not a whole lot extra. So there’s no reason you should be going with a totally “off-the-shelf” approach.

7. Get Creative

Think beyond the usual: maybe she doesn’t want more stuff. As Ralph Waldo Emerson said, “The only gift, is a gift of thyself.” The best gifts aren’t always the most expensive ones. The most important part of a gift is showing that you’ve taken time to really think about something that she’d appreciate–something that’s uniquely suited for her. Maybe you could give her an experience that would be special to her–maybe a weekend away for the two of you, or the cooking classes she’s always wanted to take. Or you could get really creative and make her something.

You don’t have to be a skilled craftsman or an artiste to make a great gift. In this case, the expression “it’s the thought that counts” rings true. You can keep it simple and make something that really touches her. Write something: a poem, a song…build something, even if it’s just a box for her yoga mat. It might sound cheesy, but you could make her a mix CD or playlist. You could have some fun with this. Maybe she goes to a kick-boxing class, and you could make her an “Ass Kicking Mix” for her iPod.

Another fun idea is making a themed “kit” or basket. When my girlfriend got laid off a few years ago, we joked about her becoming a “lady of leisure” and enjoying her time off sitting in cafes, etc. To commemorate the occasion, I made her a “Lady of Leisure Kit.”

It was a box with a collection of things to help her transition from her job into her new lifestyle: one of her old business cards and a match, a mini-bottle of bourbon and a can of ginger beer, a gift certificate to Peet’s coffee, a gift certificate for a massage, a journal (so she could record her deepest, innermost thoughts like other people in the cafes), and some other stuff that I can’t remember.

Or, if you’re not feeling the creative bug, you can always delegate. Why not have something commissioned by a local artist? It doesn’t have to be expensive. There are tons of (starving) artists you can find who would be willing to create something–maybe a sculpture or a painting–that will literally be one-of-a-kind.

I know all of this might seem a little daunting. Maybe you feel like you just don’t have any natural talent when it comes to gift-giving. I have news for you: you’re right. You probably aren’t naturally talented in this area. Which is exactly why you need to work at it and learn how to get better.

Remember, gift-giving is a skill that can be honed like anything else. All it takes is a little effort and a willingness to learn. And if you take the time to improve your gift-giving chops, you will reap the rewards, I promise. You’ll get more thoughtful gifts, your significant other will be happier, you’ll be less stressed out, and ultimately, it will create what Guy Kawasaki likes to call an “upward spiral.”