Why the big deal around Valentine’s Day? I mean it’s just ONE DAY out of the year. Maybe you are dating a woman who hasn’t painted a clear picture for you on what she thinks or how she feels about the holiday. Maybe it is something you’ve never really been into because you didn’t have to be. So what do you do?

First, you must understand that Valentine’s Day is not for us. It is for her. Seems simple right. Wrong. No real man cares all that much if his girlfriend or wife sends him anything for Valentine’s Day. But to her, Valentine’s Day is the 4th most important recognition of the year (after her birthday, Christmas and anniversary). The difference from those other holidays is that she expects you to be spontaneously romantic without having to prompt you. She might hint or tell you what she wants for her birthday or Christmas and your anniversary is actually about the both of you. Valentine’s Day is the moment you can still show her you are her man in the most romantic of ways.

If you are fortunate enough to be in a relationship with someone close to February 14th, here is something to think about: regardless of whether or not you know her real feelings about V-Day, would rather you act on the observance or not? Choose not to act and it could cost you.

So you might be thinking “Maxwell, she said Valentine’s Day is no big deal to me”, so that means I don’t have to make a big deal out of it.  Hear ye, hear ye – she is lying to you. Do you hear me? LYING TO YOU. Anytime a woman says something is “no big deal”, it is a big deal. It is a humongous deal. “No Big Deal” from a woman is a time bomb that will detonate the moment you start to believe her. She says it to you so you don’t feel pressure to go crazy. But it is far from a license not to act. You better do something or you will feel the pressure of not acting every subsequent V-Day for the remainder of your time with her.

A jewel for you: whether she will cop to it or not, a woman hates to be at work seeing her co-workers get stuff delivered to them on Valentine’s Day IF she has concerns about whether or not you’ll do anything for her on that day as well. That is not to say that you have to send something to her job for V-Day but it’s not a bad PR move if you do. (Actually, send something on occasion just to let her co-workers know that she is accounted for)

Here is something else for you: she wants to know you put some thought and effort into V-Day. Balloons are okay. Roses are cool. So is candy. Dinner and a movie is nice but if you do that all the time (like on your date nights), it isn’t special. This is your chance to mix it up and do something different. Take Valentine’s Day as an open opportunity to do something new, fun and most important – unexpected.

For example, instead of a movie, take her to a play for a change of pace. Instead of dinner, take her for a romantic picnic in the park (OK, if it is too cold – you may want to think hard about that one). Instead of a card, give her a handwritten love letter. Instead of going to a club with a DJ, take her dancing with a live band. There are multiple ways to keep things from becoming stale on V-Day. Trust, the more thought you put into it, the better.

It is wise to consider starting to planning for V-Day before the 12th of February. Wait until the last minute and if she is perceptive (she is a woman in a relationship with you – she is always paying attention), she will know and you will feel it. Depending on what you want to do, you might need 2-3 months just to get what you want for her. You don’t have to spend gobs of money to make it a great day if you plan well in advance. If you want a nice hotel suite, you probably know that well in advance of February 14th. Wait until the last minute and you will pay for the day in more ways than one.

If you’re not a naturally romantic guy, that is okay. She is with you for you and because she wants to be with you. But don’t get it confused –  V-Day is the one chance you get to step out of your “romantic comfort zone”. As stated earlier, V-Day is not about us – it is about her. Don’t screw it up by being less than thoughtful.

So is Valentine’s Day really a conundrum? I would say no if you choose not to make it one. The only conundrum to ponder is where you will wake up on the 15th if you choose incorrectly by not taking her feelings about the occasion seriously.

A man's deepest fear shouldn't be that he's inadequate; it should be that he is not pushing himself to be what he is meant to be - Max