The Wall Streeter's Guide To Not Completely Ruining Valentine's Day ... Again

It isn’t that bankers are particularly insensitive people. It’s just that they’re very busy — and the way they see it, it’s only Valentine’s Day obviously, so their date will get over it, right?

Wrong.

Even if screwing up Valentine’s Day doesn’t end with tears and regret, it makes a big check mark on the “reasons-why-I’m-so-over this-relationship” tally.

To avoid this, Business Insider reached out to veteran Wall Streeters to get a sense of what they’ve done horribly, horribly wrong on Valentine’s Day and how they’ve tried to rectify it.

Pro tip: You can’t recover from having your assistant ask your date out for you.

When the bankers ran out of ideas (it was quick), we turned to our friends at Inside Hook, a men’s lifestyle newsletter for gentlemen of a certain calibre — the calibre that does not ruin Valentine’s Day. In fact, the Inside Hook man ends up in the Valentine’s Day Hall of Fame.

You want to get into the Hall of Fame.

First things first: Experiences trump things.

Taking your date out for an awesome outing will trump presents any day. Things get lost, get old, get eaten -- experiences are memories that last forever (if they're any good).

Inside Hook has a solid Valentine's Day guide complete with some ideas to get you started. Business Insider can attest that the NYC guide is very handy, and even if you're not in any of the cities Inside Hook covers -- New York City, San Francisco, Chicago, or Los Angeles -- at least you'll know that Valentino makes a killer leather clutch.

'Don't take a vegetarian to a steakhouse.'

Stop, you're killing her.

You want your date to enjoy the evening, yes? Then know their taste.

This requires attention to detail, a skill many Wall Streeters have in their professional lives, but not always their personal lives.

Notice your date doesn't order desert? Well then your date probably won't like the box of Godiva you picked up.

Never seen your date wear a pair of earrings? Well then you date's ears probably aren't pierced.

Pay attention.

Last minute planning is expensive -- avoid it at all costs.

You could end up here. But hey, maybe that's what you're into.

One trader told Business Insider that his inability to remember to make a simple dinner reservation resulted in a last-minute thousands-of-dollars-in-jewelry shopping spree for his girlfriend.

Why? Because it takes thousands of dollars worth of jewelry to make your date forget that you forgot.

Change venues.

Just as drag queens and Oscar hosts wow audiences with a quick costume change, so too can you wow your date with a quick venue change.

'I've found that whether it's a casual thing or a serious relationship, women dig a planned venue change during the evening,' says Inside Hook editor Danny Agnew. 'Shows that you're a fella who put some thought into it. That you're not just a guy who makes a plan, he makes plans. Plural. So having kind of a blueprint of a few different things to do in an evening is key.'

Don't order take-out and pretend you cooked it.

We're only mentioning this because someone actually did it. Naturally, it was a disaster.

If your date has known you (a Wall Streeter) for more than a week, they know that you don't have time to make dinner.

If they've been dating you for a while, they know whether or not you have the skills to make the dinner, regardless of time.

The only person who has ever gotten away with that trick is Mrs. Doubtfire, and her whole persona was a fraud.

Keep this in mind.

Don't let your assistant call to make the date.

This also happened. This Wall Streeter was promptly dumped.

If your assistant calls to make the date, it makes the entire evening impersonal. Your date will likely hang up on said assistant and then turn their anger on you.

So unless that's the kind of role playing you guys are into, send a text or an e-mail instead, at least it'll be from you.

If it's 6:00 and you have nothing, don't panic. Here's a plan.

In the event that you do find yourself without a gift or a plan, do not panic. Here's a plan that will get you where you need to be in one hour, from Inside Hook CEO Jonathan Keidan.

This is what you do:

Google a simple pasta recipe. Go to your local bodega (or Whole Foods... whatever you've got). Get the recipe ingredients, candles and flowers.

Cook (try). Use the candles and flowers to create some ambience ('Do not give her the flowers, they are bodega flowers,' says Keidan). Put on some music -- try a Pandora station for a band like The xx.

Then. Take sticky notes, jot down some thoughts about how you feel about your date. Put them in places where your date will find them.

'It's about the effort and intention,' says Keidan. 'You can't be like 'this is what I could come up with,' you have to be like, 'this is for you.''

The most important thing is that you own it. Got it?

Do not under any circumstances freak out and turn to scotch. I know scotch is your friend, but you're going to need to stay alert to make this work.

Good luck.

And if you're single, you can do what you always do. ..

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