Last-minute Valentine’s Gift Ideas for the utterly clueless

It’s coming. That special day of the year that officially signifies romance but usually brings anxiety and disappointment. Yes, Valentine’s Day is coming up, and unless you want to spend it in the dog house, you’d better buy your significant other something nice. More than nice, it has to be special. Here’s what I’ve learned about buying gifts for women over the years.

The secret to buying amazing gifts

The best way to get someone a good gift is to pay attention. They drop hints, sometimes on purpose, sometimes without even realizing it. Here’s an example: Once or twice in the middle of the year, I mentioned to my wife that I thought about getting a Kindle, but that I didn’t feel like spending the money. She bought it for me for Christmas. Was I surprised? You bet I was.

What if your girl has made what she wants so obvious that you feel like if you get it for her, there’s no surprise or creativity involved? I would saying you’re probably better off getting points for your attentiveness than taking the risk of getting her something she doesn’t like because you were trying to be creative. Maybe compromise by getting her what you both know she wants, plus a little something extra that you thought of yourself.

Of course, if you’d been paying attention, you probably wouldn’t be reading articles like this one a couple of days before V-Day. So, as a favor to those who are clueless or have just run out of ideas, I’ve compiled some advice about each of the stereotypical categories of Valentine’s Day gifts for women, based entirely on my own experience. If I can’t save your Valentines Day, maybe I can at least make you laugh.


Buying lingerie for a woman is really really difficult. Beyond the simple fact that her tastes may differ from yours (you like crotchless panties, she likes Victorian lace), you also have the problem of size. Here are some lingerie mistakes I’ve made over the years:

  • Bought lingerie for a girl who wasn’t sleeping with me. The last time I saw it was when she tried it on at Victoria’s Secret. I hope she and someone else enjoyed it as much as I enjoyed learning a valuable lesson and telling this hilariously sad story.
  • Bought lingerie at the last minute at a little store inside Grand Central Station. “It looks cheap and nasty, like something a prostitute would wear” were my girlfriend’s words. Ouch. I don’t even remember what she said about the furry hand-cuffs after that.
  • Decide to hilariously subvert gender roles by buying sexy underwear for myself instead of for her (the gift would be the opportunity to see me in black briefs! Get it?). Somehow, this did not lead to sexy laughter followed by sexy Valentine’s Day sex. Oh well. At least I discovered that briefs are more comfortable than boxer-briefs.

The one mistake I’ve never made, that the sales-girls are always trying to get me to make, is to buy her a padded bra. Are they trying to get me killed? Why don’t I just give her a card that says “I love you, babe, but I wish your boobs were bigger”?

But padding is just the beginning. Buying bras is complicated stuff. Even women aren’t that good at picking the right size, according to experts. Furthermore, most bras are uncomfortable with all those wires and itchy straps (um, I imagine). Unless you find something really nice, and I mean way nicer than any of her ordinary bras (maybe something all lace), and you’re sure it’s going to fit, just skip it. Most women have one or two favorite bras that they wear all the time.

Panties, however, are a different story. She changes her panties every day (or at least she ought to), and they’re tiny so they get lost easily. This means that your average women can always use a new pair of panties. And panties are incredibly easy to buy because unlike bras, they only have one size variable. Find a pair of her panties that fits her well (i.e. don’t grab the one pair that’s always falling off of her), and check the size. You can usually find a 5 for $25 sale, so buy her five pairs and hopefully she’ll like at least one of them. I call this the shotgun approach to gift-giving — you can’t miss. Ask the girl behind the counter to gift-wrap ‘em for you and you’re good to go in the lingerie department. You may want to pick up something else though, like perfume or a box of chocolates, just to round things out so that when her girlfriends ask her what her man got her for Valentine’s Day she doesn’t have to say “Uh,…underwear”.

And one final thing: always err on the side of too small. You may be thinking, “I’m an L, and I’m pretty average, and she’s a little smaller than me, so I guess she’s an M”. Big mistake, buddy. Keep in mind that women’s sizes run a lot smaller than ours do, all the way to XXS, in fact. This shouldn’t be a problem if you checked her size before you left the house.


A woman’s olfactory glands are more advanced than ours, so don’t go thinking you can get away with buying her cheap perfume. Spend the money on something nice, that you both like and that way it’ll be a gift that gives back. If you know what kind of perfume she already wears, get the same thing or something similar. If you don’t have a clue, go to the mall and sample a few by spraying them on cards. When you find one you like, take the card with you and sniff it at various intervals throughout the day. The character of the scent changes over time.

Another thing to keep in mind is that eau de parfum is much stronger than eau de cologne, so if your woman likes to put a lot of perfume on, get her the weaker one so you can both breathe.


Yes, girls like chocolate, it’s true. That doesn’t mean that a box of chocolates makes a great gift. It’s kind of cheap, and she might think “Do you think I’m such a fatty that I’ll eat a whole box of chocolates?” or “Are you trying to fatten me up?”.

Plus, I’m a total chocoholic, so for me to buy my wife a box of chocolates would be just like the episode of the Simpsons where Homer buys Marge a bowling ball with “Homer” engraved on it (“So you’d know who it was from!”).

This seems as good a place as any to tell the story about how I sent my ex-girlfriend a chocolate penis with a nasty note. Ok, I never actually did that. But I considered it.


Flowers are kind of cheap, too. The best time to bring her flowers is when she’s not expecting them. They make a great “Just because I was thinking of you” gift, but if you send her flowers for a special occasion, you come across cheap and lazy-minded. Try a little harder, or get her flowers in addition to something else, like panties, perfume or chocolate.

I also read somewhere that the thing she likes most about flowers is not the flowers themselves, but showing off to her co-workers that she has a guy that sends her flowers, so if your girlfriend is really immature, maybe you should have them sent to the office/salon/boutique where she works.


Jewelry is actually a pretty safe bet provided you have two things: money and good taste. Trying to buy a woman inexpensive jewelry is very risky. I once bought my wife a bracelet that I thought was cool and quirky, but she thought was cheap and ugly (AND it was too big. Double fail).  But I have never gone wrong with diamonds. Every girl loves diamonds. Obviously, some like smaller, tasteful diamonds, and some like the bling. You should know which type your girl is.

If you have good taste but not a lot of money, try freshwater pearls. You can only do this a couple of times though until she figures out that they’re cheaper than regular pearls. Trust me.


I hope that I have pointed out some of the land mines in these cliched gift categories so you can avoid a Valentine’s Day disaster. But seriously, if you can do something special and original that you know will make her happy, do that instead. If not, you can fall back on the ideas above. Happy Valentine’s Day!


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