Is It Okay To Pop A Joke In A Cover Letter?

I'm about to find out.


Is it okay to:

  1. Pop a joke in a job application cover letter?
  2. Make a sarcastic remark without adding “Only joking!” at the end?
  3. Send an acerbic text message sans emoji?

All of the above. Obvs.

Look, I have a problem. I’m nearly 40, I’ve got a mortgage, I drive the most boring car in the world and I only have a second wine if I’m at an important event (read: open bar). But underneath my sensible cardigan I am ridiculous. Silly as a wheel.

It’d be okay if I lived in a cave and didn’t have wi-fi. But I don’t, and I do. As a result, many of my interactions with other humans are inappropriately cray-cray. I can’t help myself. Here’s a list of my recent faux pas:

I don’t want to use emojis. I know what they’re for. I get it. But I like to end my messages with a full stop and nothing more. No wink. No thumbs up. No boom-flossing frogs. Here’s a message I wrote last week:

How was your holiday? When’s the slide night? Oh no unfortunately I can’t make it, I’m busy.

And here’s another one:

I won’t be able to go see Mamma Mia with you tomorrow night because it will probably be a bit shit.

Verdict: Fine. My messages are mostly for close friends who like me just as I am.

Only letters and punctuation. My text messages are an emoji-free zone. (Image: Getty Images)

My publisher rejected a manuscript I’d worked on for a year. He was very kind in his email -- that’s the type of person he is -- so the rejection was disguised as a compliment. I will just paraphrase: You’re terrific, so many lovely things, blah blah, oh btw the plot was too predictable, you will never be Helen Fielding. I replied:

I'll put a tiger in chapter 30.

Verdict: Kind of okay? And if not, I could always actually put in a tiger.


I was introduced to one of my husband’s family friends at a birthday party. She asked me if I’d been to visit my brother-in-law yet (he moved to Sweden eight years ago). “Oh no,” I replied. “I don’t like him.” Then I changed the subject.

Verdict: Not great. My in-laws caught wind of the conversation and I got in trouble. My husband had to put them straight. I’m still not sure if they believed him.

Visit my brother-in-law? God no, I hate him. (Image: Getty Images)

I was having dinner with my family at a local pizza joint. While we were waiting for our meals, the kids took themselves off to the designated children’s area to draw on the chalkboard. When I went over to announce the arrival of their small Hawaiians, the father of one of the other chalkboarders said, “Your kids are well behaved,” and I replied, “That’s because I beat them,” and continued on my way.

Verdict: Well, social services never turned up.


I was awarded third prize in a competition. (I know -- third, what’s that about?!) I couldn’t make it to the ceremony, so the organiser asked me to write a short speech that she could read out on my behalf. Sure, I said, what about this:

I'm shocked and thrilled to receive this award. I'll be donating all the money to charity. Only joking -- I'll probably spend it on cheese, unsalted peanut butter and a new pair of fingerless gloves. Actually, I might take my children to the dentist.

Verdict: Bad. After the ceremony, I looked at the award website to find a reference to my amazing prize winning literary masterpiece scroll through photos of the event. There was a list of the winners … and I wasn’t in it. It was like I’d never won anything and didn’t exist.

Where the f is my award? (Image: Getty Images)

Last week, I applied for a job. In the cover letter, I thought I should briefly explain why I wanted to stop being a freelancer and start working in an office. I wrote:

Although I love the flexibility that comes with being my own boss, I would prefer to have set hours, friendly colleagues and a desk that doesn’t double as a Lego construction area.

Verdict: Don’t know yet, but surely I’ll get the job. Surely.

I asked a friend how inappropriate, on a scale of 1 to Unemployment, he thought my cover letter was. He’s a manager and has done plenty of hiring and firing. “Well,” he said, diplomatically, “what you’re really doing is testing to see if you want to work for them. Seeing if they share your sense of humour.”

Of course. He’s right. That’s exactly what I’m doing. My inappropriate communication isn’t silly; it’s a test. Basically, if you can only understand my messages if there’s a winking octopus at the end, you’re an idiot and I can’t be your friend. Only joking!