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Valentine?s Day Advice for Men

By Pete

Gentlemen, gather ’round! Lend me your ears!

Actually, never mind the whole ears thing, I’ve got two perfectly good ones of my own.

Valentine’s Day is coming up¹ and it occurred to me² that there’s a lot of bad advice out there and this day, for some reason, seems to breed stress and uncertainty. I thought I’d pass along some of the tips I’ve learned in my many years of dealing with women.

Full disclosure: I am single and, therefore, will not be using any of this advice, but it’s good, I promise.

First, understand that all women are crazy. Not all of the time, and to varying degrees, but at the core of every woman is a little nugget of bat-shit insane that you will have to deal with at some point. Stereotypes aside, Valentine’s Day does not activate every woman’s latent crazy, but if you don’t know her well enough to be sure, you should assume that it will.

This advice is probably all wrong for women who place a lot of emphasis on the amount of money that you spent, the kind of car you drive, and what your salary is (hereinafter: “materialistic bitches”). If you’re with one of these, the key is to buy her something that looks (and, ideally, is) worth roughly equivalent of the GDP of a small country. Also, it should be something that she can show off to all of her other materialistic bitch friends³.

If this is your first Valentine’s Day, the most important rule is this one: DO NOT OVER DO IT. Seriously. Many men will tell you this is because it gets her expectations up and next year will be a let-down. This is not really the case⁴. The real problem with going big in year one is that you are a man. Your natural inclination is for competition, improvement, and progress. Next year, as Valentine’s Day approaches, you will become increasingly stressed because: “Holy crap! How am I ever going to out-do last year!?” Eventually you’ll realize that you can’t (or you will, and then the year after will be a bigger mess) and you’ll feel bad.

Save yourself the trouble! Don’t think of it as “sandbagging”, think of it as “managing [your own] expectations.”

You might wonder, “Pete, shouldn’t I be managing her expectations, too?” You’re right to ask, but I’ll let you in on another little secret: by and large, women’s capacity for logic and reason when it comes to anything that they are even remotely emotional about is damn near zero. This is one of their more endearing qualities and, let’s be honest, it’s the reason the reason that so many of you actually have significant others. It’s also the reason why I’ve been able to consistently “out-kick my coverage” in relationships over the years.

This becomes a huge advantage when it comes to Valentine’s Day because it masks subtle differences in the quality of your performance over the years. The key here is “subtle”. If last year you showed up with a limo, whisked her off to her favorite restaurant, and then serenaded while you held hands and walked on the beach in the moonlight . . . a funny card and a box of $2.00 chocolates from CVS will not be acceptable.

Here’s the thing. Yes, your girl would be thrilled to have a made-for-TV Valentine’s day complete with all of the cutesy, romantic trappings. Most women, though, have been dealing with real men for long enough that they know this is unlikely to occur, and they have conditioned themselves to be perfectly happy as long as whatever it is that you do demonstrates, at least to them, that the following three things are true:

1. You spent some time thinking about it and therefore, by extension, her. If your Valentine’s Day overture looks like you picked it up on the way over to her place because you had forgotten about it prior to that, you have failed.

2. It is a genuine representation of your feelings. By now, she is probably used to your constant endeavors to get into her pants. She probably even thinks it’s kinda cute. What she will not find cute are grand romantic gestures that seem contrived or calculated in an attempt to get a little action. This is especially true early on.

3. You care about her (and all of that other emotional crap). This is the big one. We can have a lengthy debate about how fair it is that there’s a whole holiday dedicated to showering our women with affection while we men are still struggling to get people to take Steak & BJ Day seriously. If you’re smart, you’ll pass on the debate at least this month. Really, in a woman’s mind⁵, all she really cares about is that whatever you do convinces her that you still think she’s wonderful.

Now, trying to figure out what you can do to get that message across can be quite daunting, and you know I wouldn’t leave you hanging, so here are some tips. Your mileage may vary.

Do not send her an e-card/email/text. Do not. Do not. Do not. If you’re to the point in the relationship that you should recognize Valentine’s Day and her role in your life, you are already beyond e-cards. That’s not to say that emails and texts and such cannot be a small piece of a larger initiative, but one text message, sent from the bar at 9:00pm that says “luv u” is not sufficient.

With respect to flowers: a few of her favorite flowers⁶ will probably be more impressive to her than three dozen roses.

Write in the damn card. For the love of god, do not just open the thing and write “Love, Jim” on the bottom and call it a day. I don’t care how sappy the actual card is, she doesn’t really care about that. She doesn’t care what some underling at Hallmark thinks. She wants to know what you think. You don’t have to write a novel or a sonnet. You don’t have to be particularly eloquent. Hell, it doesn’t even really have to make sense. A few sentences about how fantastic you think she is will go a long, long way. Coming up with what to write will probably take you longer than the rest of the planning combined, but don’t stress too much, you almost can’t screw this up⁷.

Do not fight with her. Seriously. You don’t have to concede when she says your mom is a bitch. You don’t have to agree that Auburn is a superior football program to your beloved Crimson Tide. But your options are limited in disagreement. The sentence “I’m not sure I see it that way” followed by deftly changing the subject can save your life. This is not the day to make your stand.

Try to be creative, but don’t kill yourself in the effort. If you’re reading this post for advice, you are not the kind of guy who is going to come up with something amazing and creative every year. Some years you are just going to have to do the flowers and dinner thing. You should try to change it up from year to year (god help you if she gets in her head that there’s a formula), so if you did roses and a fancy dinner last year, maybe this year you should get a different kind of flower (her favorite, maybe?) and cook for her. Or do something nicer for lunch and then do something really low-key in the evening. Bottom line: the execution here is more important than how creative you are. You can do cliche as long as you do it well.

Pro-tip: If you have done cliche two years in a row, get out your outlook calendar and add a reminder for October. Set aside some time in advance to come up with something creative and “cute” to do next year. This type of thing is so, so much easier when you don’t have the stress of the actual day bearing down on you.

Finally, the most important thing you can do to make the day a success is chill the fuck out. Relax. Few relationships are won or lost on Valentine’s Day. There is very little you can do that you cannot make up for and virtually nothing you can do that will guarantee you a free ride until next year.

Remember: not only is your girl not sitting around and comparing your Valentine’s Day effort to last year’s, or her last boyfriend’s, odds are that she’s actually completely incapable of doing so given her emotional attachment. She’s not keeping a little scorecard: “Flowers: Advantage, 2008. Card: Advantage, 2009. Dinner: Push.”

She just wants to know that she’s an important part of your life and you like having her around.

And, really, if you follow all of this advice and she’s still not happy? That girl has issues and unless she’s waaay above the Vicky Mendoza Diagonal, you don’t want any of that.

Good luck, gentlemen. You can do this, I have faith in you.

Now go make it happen.

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1. Tomorrow, if you’re somehow unclear on that.

2. After getting an email with the subject “Reminder: Send a Valentine’s Day eCard today”.

3. They run in packs, you know.

4. Materialistic bitches notwithstanding.

5. This is a figure of speech. Nobody really knows what goes on in there.

6. If you do not know what her favorite flower is, you really need to figure that out, and soon.

7. Almost. Don’t push your luck. “You’re almost as hot as your sister,” no matter how impressive that is, will not go over well.

Full post as published by PeteHoliday.com on February 13, 2009 (boomark / email).