A Cynical Guide To Valentine’s Day

A vacation is also a gift to yourself

I won’t lie. I love Valentine’s Day. It’s not because I am some hopeless romantic or benevolent lover who finds pleasure in making other people happy. In fact, the day itself can be tedious and the commercial aspects are rather tacky.

But Valentine’s Day is a game. And like all things in life, I don’t want to lose. So, I’m going to take control, eviscerate her expectations, transcend all benchmarks, and vanquish any would-be suitors with a ferocity that makes her think that I actually care.

Here are some fairly simple, yet effective things I’ve learned for ensuring a victorious Valentine’s Day.

Stay at home on the big day.

  • Prix fixe menus are bullshit. If I wanted a complimentary glass of champagne, I’d board my flights five minutes earlier.
  • And a set menu probably won’t have any prices on it. Especially if it’s a new relationship, she really should know.
  • Instead, line up a thoughtful, home-cooked meal at your place. Focus on the booze (saké is a great wingman), a meal within your culinary comfort zone, and a classic romantic comedy.
Yellowtail sashimi with jalapeños and ponzu sauce is a personal favorite

Celebrate the fancy restaurant meal the night before, or the night after.

  • It’s less crowded and you won’t get price-gouged.
  • You get to avoid the 2,000-calorie, 8-course prix fixe meal that turns into the most ironic cock-block in history three hours later
    when she just wants to go to sleep.
  • If you work in fíñäncé, you can probably expense it.

Always send flowers to her office.

  • Under normal circumstances, sending flowers to her office is a terrible idea. It’s like a giant neon sign that tells all of her
    colleagues that you screwed up.
  • But on Valentine’s Day, women are hyper-competitive. Make sure it’s either alive, or comes in a decent vase. Nothing is worse than forcing her to lug home some thirsty bouquet on an evening when Ubers are scarce.
Reinvent the Valentine’s Day bouquet
  • Send her something she can keep in the office for more than just a few days. I’d recommend orchids or a hand-crafted garden box.
  • Not only is it a great daily reminder of you, it’ll help ward off any office competition.
  • However, if you think she might be cheating on you, send her flowers anonymously. If she never mentions them, dump her.

Opt for a romantic vacation instead of jewelry.

The Hotel Jerome in Aspen is the getaway of her dreams — great food, booze, skiing, and romance
  • Jewelry is great. But save that for Christmas, birthdays, and for when you really screw up.
  • A vacation is a gift that you get to enjoy too. And during the trip, she’s going to be much more inclined to demonstrate her appreciation.
Christopher Cloos is hot right now — 0 to 350 retailers in the last 14 months
  • Instead of simply giving her a printed itinerary, present it with something relevant to the trip, like a sexy leather passport holder or some really cool unisex sunglasses from one of the hottest, emerging Scandinavian brands.
  • Skip a a destination you might have visited with a previous lover. It’s harder to relax when you have to pretend like you’re not re-living some old memories.

No spa certificates. Period.

  • First of all, gift certificates are for poor people — a scam to dupe lazy people into giving errands to their loved ones.
  • Secondly, it’s not-at-all thoughtful. Going to the spa shouldn’t be treated like some special occasion. She should be making spa visits on a regular basis, mostly for herself, but also for your benefit.
  • It’s shouldn’t be too hard to come up with some ideas for any stage of a relationship. I like the seductive confinement of a heavyweight down comforter which also helps to alleviate anxiety and insomnia, a Bvlgari cocktail clutch, or some sexy, chic denim jeans that are more comfortable than sweatpants.
Mott & Bow jeans are the real deal — style, comfort, quality, and value

Don’t even think about proposing.

  • It’s vapid and obnoxious, especially if done in a public setting.
  • The odds aren’t in your favor — the average marriage that started out as a Valentine’s Day proposal lasts less than two years.
  • However, there is an upside to getting engaged on Valentine’s Day. At least you won’t need a prenup. You’ll get your Xbox and cargo short collection and she’ll keep her Instagram drop shipping startup.

There you go! Get out there, shower, manscape, put on your finest, freshest boxer briefs, and kick some ass…

And always remember, your performance on Valentine’s Day will be seen by other women. Use this stage as an opportunity to line up other prospects.