How to Ask Out Your CEO on a Date

How to ask out a CEO

CEOs are the envy of the natural world—supremely hardworking, supremely talented, supremely gifted, supremely successful, and supremely rich.

Regardless of whether they look like a clump of manure after a rainstorm, complemented by the personality of an outraged walrus, some employees may want to date one of these things (the CEO, not the manure).

This is a complex matter regarding much tedious legalese and chin stroking pontifications. As such, we’re on hand with legal advice on the ins-and-outs of attempting to date a supreme overlord.

The Employment Law Behind Asking Out a CEO (chief executive officer)

A chief executive officer is a form of employment. Like any job, there are certain tasks involved in doing it. These include:

  • Yelling at people.
  • Pointing dramatically at graphs.
  • Muttering “profit margins” every 35 seconds.
  • Instantly dismissing people to look tough and important (then facing unfair dismissal claims in the aftermath).
  • Earing a six-figure salary.
  • Constantly claiming to work harder than everyone else.

Inferior employees are encouraged to keep their distance from a CEO, thus ensuring they don’t interfere with the gravitas of the aforementioned CEO and his/her bombastic drive towards earning more profits.

However, some employees may be insane enough to try and ask out a chief executive officer

Making advances on a CEO is legislated by The Asking Out a CEO at Work Act 1974 (additionally, see flirting at work laws and The Flirting in the Workplace Act 1974). Here’s a case study to make this situation more understandable.

“Jeff the janitor had a thing for his millionaire CEO Bob. Jeff would scrub the office floors (even the carpeted ones) extra hard with his mop to try and win the affections of Bob. He mopped better than anyone else had ever mopped.

Sadly, Bob wasn’t interested in lowlife scum such as janitors.

Unfortunately, Jeff didn’t take this into consideration. One morning, while mopping really, really, REALLY hard at the carpeted bit of the office’s floor, Bob strode purposefully out of a meeting and passed the gobsmacked Jeff. Bob ignored the janitor. Jeff blurted out, ‘Fancy a pint tonight, mate?!’

In the aftermath of this calamitous exhortation, Jeff never worked as a janitor ever again. It’s believed he now is in prison (as a security guard) and has since found someone as pathetic and inferior as he is to go out with and happily marry etc.”

Jeff’s tale should be a warning to the rest of humanity. CEOs are essentially superhuman and akin to Batman.

Should an employee ask Batman out on a date? No, they should not. Think of all those bats everywhere! Plus, you know, we think Christian Bale is married anyway.

But the point is CEOs work 24/7, never sleep, probably are robots (or aliens), and they’re only ever going to be interested in people as rich as they are. Alternatively, if the employee happens to be extremely good looking by happenstance, figures they may as well try asking out your CEO anyway.

Chat Up Lines to Use on a CEO

Even the lowliest, poorest, and most pathetic employee may still have a crack at asking out a CEO. The Asking Out a CEO at Work Act 1974 contains a list of chat up lines employees are legally permitted to use on a CEO.

These chat up lines are, specifically:

  1. “Get your coat, you’ve pulled.”
  2. “Aside from being sexy, what else do you do for a living?”
  3. “Do you like raisins? How do you feel about a date?”
  4. “If I could rearrange the alphabet, I’d put ‘U’ and ‘I’ together.”
  5. “Do you believe in love at first sight? Or should I walk by again?”

The above five are legal and can be used repeatedly, or in combination, with each other on a CEO. However, users of these lines should note they aren’t guaranteed to succeed.

In fact, using the lines may result in the chief executive officer of your dreams giving you a look of:

  • Revulsion.
  • Disdain.
  • Disgust
  • Hatred.
  • Dismay.

If any of the above occur, a date is unlikely.

However, if by some miracle one of the chat up lines does succeed, employees should be aware of the procedures and policies involved with regard to taking a CEO on a date.

What to Do on a Date With a CEO

CEOs are used to living the high life. As such, an employee’s standard dating tactics of going to the cinema or eating at McDonald’s want wash here.

Employees will need to splash out and/or make a grand gesture. Suggestions for this include:

  • Booking a first class ticket to Paris to dine out at a Michelin starred restaurant.
  • Renting a supercar and turning up to take the CEO joyriding.
  • Renting a private jet and flying to the Bahamas for a beach date.
  • Burning money before gross poor people whilst laughing hysterically in an attempt to impress the CEO with your wealth.

Keep in mind, even the above tactics will likely fail with a CEO as they’re so used to avarice and luxury. Even the best, most glamorously fashioned intentions will probably fall flat and be construed as feeble and peasant-like.

As such, employees on a date with a CEO should head into the date expecting to fail miserably.

Again, that’s unless the employee happens to be extraordinarily good looking. In which case they should simply flutter their eyelids and hope for the best. A trip onto the CEO’s private jet is only a debasing low-cut top (or tight pair of leather trousers) away!


  1. Alternative strategy – dress up as a great white shark at work so your CEO will be loath to refuse your advances! Of course, this means you’ll have to enjoy the future sexy times and wedding day with the CEO as a great white shark, but that is a small price to pay to live a life of luxury.

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