Valentine's Day Advice

I'm getting lots of requests in Reader Mail to share my wisdom around Valentine's Day. I'm a guy surrounded by women, and I've got a bit of a reputation for being a great gift-giver, so what do I suggest...?

1. Do something...ANYTHING. Ignoring February 14th is not an option. The day exists. Start by accepting this simple fact. "It's a greeting card holiday"; "It's all about retailers and florists moving product"; "I don't need to do something one day a year to show you I love you". True as these statements might be, these are called 'excuses' when you use them, and these are called 'setting yourself up for disappointment' when your loved-one does.
2. Get/make a card. This is the one gift-giving event where the card is more important than the gift. A great card with a crappy gift is what your loved-one loves about you ("What a moron, but he/she is sure thoughtful"). A great gift with no card might as well have come from a gift exchange at the office ("Wow. Nice gloves. I wonder who they're from?") Furthermore, write something sweet and mushy on the card. Whatever you write, it should be unusually sappy and vulnerable-sounding. If the card merely repeats what you say every day than it might as well have been pre-printed. Even terrible poetry written with sincerity is better than "I LOVE YOU XOXOX", if you're already at the point in your relationship where those 3 words have become as commonplace as "Good morning!" or "Would you mind making me a coffee?"
3. Sign the card and put your loved one's name on the front of the envelope. This avoids any confusion about the from-whom and the to-whom. It can also avert disasters in the case where ambiguity might be involved or multiple-loved ones are receiving cards (e.g. Husband/Wife card is a little sexy, and other family members are also receiving cards). A little doodled heart on the envelope is a nice touch. When you sign the card, don't use your last name (I hope I don't need to explain why).
4. Take a chance on the gift. It doesn't have to be expensive, but it has to demonstrate thought and effort. Think hard about your loved-one. Try to remember something that he/she mentioned 4+ months ago that you could only possibly remember because you love them so much. Try to get something he/she wants but that you couldn't possibly know he/she wants. Avoid kitchen appliances, weight-loss or fitness paraphernalia, wrinkle-removing lotions, or anything else that can be taken the wrong way. Keeping all that in mind, take a risk on something that you genuinely believe reflects your deep affection. Even if it's stupid, stupid-genuine works.
5. Avoid the easy way out. It's easy to say "no gift, but I'll take you to dinner" or "no gift, but I'll make you a nice dinner" or "he/she really liked last year's pedicure gift card so I'll do that again this year". Valentine's gift-giving is not like golf, where consistency in your swing is what wins the round. It's more like kick-boxing where you're trying to keep your opponent off-balance and vulnerable through deception and mis-direction (I know nothing about kick-boxing, by the way, but I'd guess that deception and mis-direction is probably better than doing the same thing over and over). 
6. Be very cautious when it comes to Valentine's gifts/cards for multiple loved-ones of equal standing. Let's say you have three daughters, for example. They all need to receive exactly the same thing from you, personalized in exactly the same way. This can mean three doggie cards, with three different doggies that are somehow directly relevant to each of your three daughters, but the doggies must be equally cute. And you must give exactly the same number of "X"s and "O"s if you're doing the XOXOXO thing. If you're drawing a little heart on one card, put one on each card that is precisely the same size. If you're saying "I love you, <name>", keep font-size and swirling letters as equal as possible. Buy gifts that are directly equivalent if not exact. Keep prices consistent. Understand that all of these variables WILL BE compared and somebody will feel shafted if anything is off-kilter.
7. Be excited. Do you love your loved-one? Are you about to make him or her happy? Isn't that the most important thing you can do on this planet? You should feel excited. You should have butterflies in your tummy (I don't think I've ever said "tummy" before in a post, but "tummy" is the kind of word that resonates around Valentine's Day). If you're doing this right, you should feel out-of-your-comfort-zone and very vulnerable. Don't hide it. Don't suppress it.  Embrace it! You are Kevin Costner in Tin Cup, firing ball after ball into the pond because you're trying for that perfect shot. Don't pull up. Go for it. You're not going to win the Masters, but you're certain to win his/her heart.