Question: How do men feel about this day? In your mind, what does a man do on this day to impress a lady, and how can he fail miserably?

Al Batrosse

To be honest all men I know count the days like dollar signs through Valentine’s Day. First there is the pre-V-Day Winterlicious dinner. With drinks it costs approx $100. And it may lead to hints about trying another restaurant you missed at Winterlicious come V-Day. (Winterlicious cleverly ends Feb. 12th). The meaningful and thoughtful gift is a huge pain in the ass unless she has casually shown you something that she really likes at some previous point.

To impress? I say the Valentine dinner has to be made from scratch at home with some care. And there should be a lot of good booze and you should listen to your favourite songs and dance on the couch.

Failing miserably is my middle name. Simply buy a whacked out Valentine’s Day gift, say Cheap Trick box set, then completely overreact to her visible disappointment. Bonus points for telling her that "her little work buddy" can go buy her a perfect gift.

John Smith

The premise of the question pretty much sums up this day: guys HAVE to impress a lady on Valentine’s Day. Women don’t (and probably shouldn’t) have to do anything except putting some effort into looking good. I could go into what’s the best date to plan, present to get, etc. but since this isn’t hedoesthecity.com let’s use this forum on the 14th to see what your big day means about how much your date cares about you. I think that’d more interesting to the readers, right? Right.

First off, know this: guys don’t care about Valentine’s Day. We don’t sit around with our friends talking about our plans beforehand or dissect the evening afterwards so it just doesn’t resonate with guys in the same way it does for girls. Soooo…Everything your date does, he’s doing it for you (tangential Bryan Adams reference completely intended).

I tend to think that girls like to be taken out so I kinda disagree with Mr. Batrosse but perhaps your guy is broke and you can’t fault him for that. Whether it’s a nice restaurant or he cooks, the main thing is effort. If he puts some thought into it and makes the night special he’s probably a good guy and he likes you.

Did he dust himself off and put on some clothes that weren’t on his floor? Good.

Did he plan ahead to get a reservation at that restaurant you’ve said you wanted to try or choose a complicated recipe that involves a food processor and cheese cloth? Nice going.

How ’bout the sheets? Were they clean? Now we’re talking.

If he takes you to a Chinese place with glaring, fluorescent lights because "everything was booked" or orders a pizza because "we don’t need a special day to celebrate our love" he’s probably not that into you but at least you can round up your girls to go see that terrible movie and talk about what a dick your EX is.

Vinny Valentino

Valentine’s Day is like taking the car in for its annual checkup. The date arrives like the careful spin of the odometer every year reminding you to check under the hood and see if everything is OK. Valentine’s, if anything else, makes you take stock of your relationship. If you are sweating and worrying about this date you know there is something wrong under the hood. Ah the dread! Ah the money that will have to be spent! You should not have ignored that rattle all this time. So this kind of anxiety hangs over Valentine’s: doing the perfect ‘thing,’ getting the right gift, not getting Winterlicious reservation weighs on you. But… doesn’t this gut wrenching make you realise – hey maybe – you’re driving in a lemon! Time to Craigslist.

If, on the other hand, you show up early to the dealer hand him the keys with a smile on your face — it’s because you know you’ve added oil when it’s needed, been easy on the brakes and washed off the salt. Because you’re cruising with some top-knotch chrome. Your day at the garage is easy, worry free. Much as Valentine’s SHOULD be. You can take home the dealer’s complimentary scented tree air freshener home to your girl and she’ll love you like chocolate.