What started off as a discussion on Valentine’s Day quickly morphed into a full-fledged debate replete with divine revelations as well as detailed sermons from some of our most verbose colleagues. It became clear that often what’s neglected in the multitude of blogs, papers and self-help guides tailored around Valentine’s Day are tips telling guys what not to do in order to prevent this day from turning into a disaster.

1 – Do not propose to your girlfriend

As a society, we’re ingrained with the mentality that Valentine’s Day carries a little extra weight even though it’s just one day out of 365(.25) other days. Though that seems a bit reductionist, think about it – all you get are high expectations, especially on the part of women, which sets the bar higher for men to do something that’s so eye-catchingly special, that it actually makes an impression on his significant other and stands out for its originality amongst the rest.

See the thing is that women kind of half-expect something special on Valentine’s Day, so if you want to surprise them, you’ll need to go above-and-beyond in originality to counter their expectant nature and still dish out a surprise.

The first thing a women does when proposed to, is tell her friends about it. All her friends. The next she does is show off her ring, which you obviously want her to appreciate because you only spent your last 3 months of salary, not to mention search effort, travel time and stress finding that one perfectly cut stone to adorn her slender digits. So you want to make sure that when she does tell her friends, and she does show off her ring, she’s the only one doing it.

Chances are someone she knows might also be proposed to on Valentine’s Day, so if she has to compete with her friends for short attention spans in making her good fortune known, she’s probably not going to appreciate it. If everyone’s comparing rings at the same time, then what’s worse is that you’ll (yes, the blame will fall on you) be “blamed” for somehow detracting from her moment of specialty. If you are going to propose (or if you’re not), avoid Valentine’s, but be sure to gift her with something she values – perfume, chocolate, flowers, and scented candle are seasonal favourites. If you are tight on budget, be sure to take advantage of comparison shopping sites to save a few bucks in this quest.

But if you do choose to propose to her on Valentine’s Day (though we fervently wish that you don’t), the onus is on you to make it a blisteringly memorable event that outperforms even the best of all her friends’ stories. Good luck!

2 – Do not do nothing

This one’s for the married couples out there. There have been too many instances when the wife has usually said something on the lines of “Don’t do anything for Valentine’s Day this year honey [insert possible reason – RRSP payments etc]”. Should you listen to her? A resounding NO!

Do something – take her out to dinner, watch a movie – because if you don’t, she’ll be mad. If you’re married, you want to make an extra special effort to remind her that you do, in fact, remember the special days (thereby hinting to her that you will make a special effort to remember the wedding anniversary). Remember, to you it may only be one day in 365(and 0.25) but to her, it means something more, so you want to make it special for her, and chances are, like most women, she’ll end up talking about it for a week, so make it good. Again, pamper her with gifts and presents, but not too many. And while you’re at it, make them meaningful and not gimmicky. A brand new smartphone, bottle of perfume, or even the new Apple iPad would all be welcomed, while chocolates and flowers would all be standard, and expected.

3 – Do not screw up on timing

For example, don’t buy and deliver flowers to her in private. Always go for the public route. If you’re shy and don’t want to deliver it to her in person, at least make sure that it’s there for her in public, so that everyone knows she’s loved and cherished.

A colleague compares women to marinated meat. If you want to be prepared, you don’t hastily marinade (i.e. prepare) the meat (your “other”) right before you want to prepare a meal (i.e. treat her to a wonderful time). You have to instead prepare her…um I mean the meat… in advance. Start earlier in the day, take your time to flatter her and pamper her. Make her feel good. Have flowers delivered to her in her workplace so that she feels special (this also makes sure that she’s in a good mood even after she comes back home) and then do whatever it is you’ve planned to make the day special.

Don’t buy her flowers at the end of her day. First of all she’s going to be miffed that you didn’t do anything to cheer up her work day, and if she finds you hastily mollifying her when you come home, you’re going to look disorganized and careless, which in turn will convince her that you don’t really care about Valentine’s Day…you can see where this might lead.

Timing and patience is key if you want to make it good. Butter her up throughout the day, and be sure to send her just the right number of presents and treats. Not too much because then it’ll look tacky, but not too little that she appears neglected when she relates her experience back to her friends afterwards.