14 Strange Requests That Assistants Received at Work

Being an executive assistant often means wearing a hundred hats—planner, therapist, miracle worker... and occasionally, mind reader. But while most tasks stay within the realm of sanity, some bosses and VIPs push the boundaries of what a “reasonable” request actually is. From absurd errands to eyebrow-raising personal favors, these executive assistants have seen it all—and lived to tell the tale.

• I worked for someone who vacationed every year in the Caribbean for 15 days (I think he had a timeshare). He called me and asked if I would pick him up toilet paper and FedEx it to him, since they didn’t like the toilet paper in the timeshare. I asked what brand. He said he didn’t care, and I replied everyone has a TP preference, in the end, his was Cottenelle.
  I also had to send a package by FedEx each day with copies of any important mail, the daily newspaper and other items. I think him and his buddies would compete to who had the better “girl” working for them. He was very old school, and this was the 90s. He was a good guy. © Bobkst320 / Reddit
• I was working for this married man who definitely didn’t act married. One day, his wife stormed into the office and demanded I call him. When I did, he whispered, “Don’t move a muscle. She’s got one heck of a temper.”
  I wasn’t sure why I needed to stand still, it wasn’t like I’d done anything wrong. But he definitely had. “Get rid of her,” he cried, his voice trembling, “She’s got a temper, remember.”
  “I understand, sir,” I said calmly, and put down the phone. He could see us through his office window, but he couldn’t see the left side of my desk, so I did something I knew he wouldn’t see coming.
  I discreetly slid her a note with a name scribbled on it—the name of his mistress. They got divorced, I got fired. Worth it.

• A colleague told me they supported a woman who hired her boyfriend as a consultant. They then would travel around together, and she’d approve all his crazy expenses.
  By the way, she had a husband who wasn’t privy to any of this information. © BuffetofWomanliness / Reddit
• She regularly traveled to the West Coast and back to the East Coast, and somehow never figured out that coming back you can't get from LA to Raleigh by lunchtime. It was always a problem when I booked her flights, she wanted to be back earlier but refused to do a red eye. I came this close to snarkily asking her if she wanted me to invent her a time machine on top of all the other miracles she expected. © ThunderChix / Reddit

• I had to get my boss a passport for a trip that was supposed to happen in a week—did all the paperwork, phone calls, and leg work to do it… He never even ended up going on the trip!
  And when it arrived, I told him to put it in his safe. A week after putting it in his safe he found his old one in his briefcase (well, his housekeeper found it I should say!). But to be fair the old one was expired so we would’ve had to get a new one anyways. © Historical-Promise-4 / Reddit
• Asked me to make flash cards with each staff member's name on one side and their picture on the other. For 80 staff members. She wanted to learn who everyone was. My co-workers laughed at me when they walked by and saw what I was doing.
  She had lots of other kooky requests, and didn’t fit in with the company culture very well. She even brought her cat to work and left it in her office one day. Anyway, she was let go 6 months after she started. © Frosty-Cupcake-7820 / Reddit

• Find out who has the best Reuben sandwich between here and a neighboring city about 40 miles away... This was in 1986, so there was no looking at Google reviews of about 100 restaurants between the places. He was a lawyer. © Signal_Violinist_995 / Reddit
• I was an EA/PA to a legally blind gentleman for over 3 years. To say my job was unorthodox is an understatement. Let’s just say that "no job is too small" takes a new meaning when you work for someone that literally can’t see. He also used to accidentally email or text me instead of his dates during his bachelor phase.
  My favorite story though is when he lost his passport before an international flight. Luckily, I had a days notice and live in Manhattan. He paid for me to stay in a hotel by the passport agency.
  I woke up at 4am to get in a line that was already down the city block, waited in that line all day, and then had to vouch for his identity since he didn’t technically have another form of identification. (Luckily, I have a great memory for random stuff and knew his personal info off the top of my head).
  Passport in hand, he made his flight and had a great time! Months after I left that job, he texts me that they found the missing passport! © Illustrious-Bid1158 / Reddit

• Feeding his two donkeys! © Swim_the_Sea / Reddit
• While going through the IVF process, she had me inject her with hormones to help increase her egg production. © chikpea16 / Reddit
• Wash his Mercedes with a special soap. Walk his dog. Watch his kids. Clean up his home after a meeting there.
  Have my desk next to his so I could work and listen to all his meetings. Take on the job responsibilities that his HR lover had so they had more time together... © sassy_chick67 / Reddit

• Being asked to coordinate a chicken nugget eating contest by my CEO at 1-hour notice for my entire office. Had to order thousands of nuggets. McDonald’s thought it was a prank call when I ordered. Then had to lug them back to the office myself.
  My CEO made me time them, stuffing their faces, and told me I wasn’t yelling "times up" loud enough. Then had to clean up all the rubbish after. © luce82143 / Reddit
• I was working a horrible contract position. Every day, the boss would tell me what he wanted me to get him for lunch. Often he wouldn’t give me the money for it.
  One day he did pay me back, but he handed me a large ziplock bag with a little over $20 in nickels, dimes, pennies and quarters. © StraightPotential1 / Reddit
• Mail out his mistress’s divorce papers... © Forsaken-Two-912 / Reddit

Behind every polished executive is someone quietly juggling chaos—and doing it with a straight face. These executive assistants have definitely earned their superhero capes.

And while some jobs come with wild requests and terrible bosses, others are just fuelled by pure, contagious passion. Check out these 20 stories about people who love their work so much, they can’t stop doing it—even outside office walls. It’s proof that work doesn’t always have to feel like... well, work.