“Laughter is the shortest distance between two people.”

– Victor Borge

Humor is a great way to build any relationship, whether connecting with new people or creating new business relationships.

It can be a very powerful tool for any Salesperson. Humor has the power to break down barriers, lighten the mood, and bring people together in a way that other things can’t. 

It breaks the ice, builds rapport, and can make their pitch more memorable and increase the likelihood of a positive outcome.

People are more likely to remember something that made them laugh or smile, 

Being humorous requires effort as it’s a creative skill. But with crazy technology such as ChatGPT, you can now become the most humorous person out there. 

Here are a few types of humor emails that you can use to get connected strongly with your prospects.

  • Personalized humor
  • Storytelling
  • Wordplay
  • Self-mockery
  • Observational humor

“Laughter is the sun that drives winter from the human face.” – Victor Hugo

Leverage these ChatGPT prompts, and send humorous and the most relatable person that everyone enjoys talking to.

1. Personalized humor

Prompt 1

Give an email that shows the SDRs go too far to get prospects’ attention. I’m reaching out to a potential client. Make it hilarious.


Subject: Do you believe in love at first sight, [Prospect]?

Hey [Prospect],

I was scrolling through my LinkedIn feed and stumbled upon your profile. It was like love at first sight (at least for B2B purposes).

I must confess, I went a little overboard to get your attention. I may have put up a billboard with your face and contact information and sent a singing telegram to your office. But hey, I figured if I was going to shoot my shot, I might as well aim for the stars.

Your experience and skills are exactly what I’ve been searching for to take my business to the next level. Can we grab a quick call sometime this week to chat and explore how we can collaborate?

Looking forward to hearing back from you!

[Your Name]

P.S.: Please don’t file a restraining order against me. I promise to keep it professional from here on out!

This email can put a smile on the reader but not every prospect would find it amusing.

In order to use humor effectively, it’s important to consider the context that is appropriate and relatable to the audience.

By tailoring the humor to the specific context, it’s more likely to be well-received and has the desired effect.

Focus on Personalisation

As the famous comedian Ellen DeGeneres says, “When it comes to comedy, knowing your audience is half the battle.”

If you want to be truly humorous, focus on connecting with your audience. You got to personalize your emails with something that is closely connected with your prospects.

You can get this information from prospects’ social profiles like Linkedin and Instagram.

Here’s an example of cold emailing a prospect who is a Tacolover:

Prompt 2

Give an email that shows the SDRs go too far to get prospects’ attention. I’m reaching out to a potential client. Make it hilarious. The prospect is a Taco lover.


Subject: Can I bribe you with tacos, [Prospect]?

Hey [Prospect],

I hope this email finds you well and hungry for some delicious tacos. I mean, who doesn’t love tacos, am I right?

Anyways, I couldn’t help but notice your LinkedIn profile and I have to say, your experience and skills are truly impressive. I think you could be a perfect fit for our company, and we could be a perfect fit for your appetite.

So, if you’re interested in discussing this further over some tasty tacos, let me know! I’ll even throw in some guacamole to sweeten the deal.

Looking forward to hearing back from you,

[Your Name]

The same email above can be improved when reaching out to connect well with a Mexican Prospect –

Prompt 3

Write an email that shows the SDRs go too far to get prospects’ attention. I’m reaching out to a potential client. Make it hilarious. The prospect lives in Mexico.


Subject: ¡Hola amigo! Let’s Taco ’bout your business

Hola [Prospect],

I was searching for businesses to work with in Mexico and I stumbled upon your profile. I’m not going to lie, I’m a huge fan of Mexican food and the fact that you’re based in Mexico City just made my day.

I’m an SDR with a sense of humor, and I believe that a good laugh can make a business relationship stronger. That’s why I’m reaching out to you with a ridiculous proposal. Let’s taco ’bout your business! I promise I won’t make any more cheesy puns.

But on a serious note, I believe that we can do great things together. I’ve done some research on your company and I think our solutions could really help you achieve your goals. Can we schedule a quick call to chat further?

Looking forward to hearing from you, and maybe even sharing some tacos in the future!

[Your Name]

While personalizing your cold emails it’s best to have common ground that you can connect with your prospect to create a sense of belonging rather than sending out the hope this email finds you well.

Some of the topics that you could leverage to build personal connections with the prospects are –


Almost everyone needs to eat, and many people are interested in trying new foods or learning about different cuisines.

According to a study by Hunter Public Relations, 69% of Americans consider themselves “foodies” and enjoy trying new food experiences.

Movies/TV shows

According to a survey by Nielsen, 90% of US adults reported watching TV shows and 87% reported going to the movies.

This suggests that a large percentage of people may be interested in discussing their favorite shows or movies.


People generally enjoy talking about their travel experiences, and many aspire to travel more.

According to a survey by TripAdvisor, 60% of US respondents planned to take a leisure trip in the next 6 months.


Music is a universal language that can connect people from different cultures and backgrounds.

A survey by MusicWatch found that 90% of US respondents listened to music every week.


Many people are passionate about sports and enjoy following their favorite teams or athletes.

According to a survey by YouGov, 57% of US adults reported being interested in sports.


While many people may own pets and love them, this topic may not connect with everyone.

A survey by the American Pet Products Association found that 67% of US households owned a pet in 2020.

You also pick more non-prominent topics like Fitness, Culture, Wine, Outdoors, Gaming, and Arts as well depending on your target prospect.

Here’s a great example of getting the attention of a potential customer who had his dog on some of his LinkedIn posts –

Prompt 4

I’m reaching out to a potential client who is a dog owner. Can you help me craft an email that will grab their attention and show that we share a love for dogs? Let’s make it playful and suggest that their pet could be our office mascot.


Subject: Woof Woof! Can [Prospect]’s pet be our next office mascot?

Hey [Prospect],

I hope this message finds you well, and that your furry friend is doing great too! I came across your profile on LinkedIn and I couldn’t help but notice the adorable picture of you and your pet. What a cute duo!

As a fellow pet lover, I thought I’d reach out and see if there might be some potential synergy between our companies. I’m not sure if your pet has any business expertise (although I wouldn’t be surprised if they do), but I’m sure they’d make a great addition to our team as an office mascot.

On a more serious note, I came across your company and was impressed by the amazing work you’re doing. I think our companies could work together to create something even more amazing.

Would you be interested in a quick call to discuss potential collaboration opportunities? And if your pet wants to join the call, that’s totally fine with me.

Looking forward to hearing back from you and your furry friend!

[Your Name]

2. Storytelling

Humans are wired to respond to stories, and a well-crafted narrative can captivate attention and create a memorable impression.

When a story is used in a cold email, it can help to break down the barriers that often exist between a salesperson and a potential customer, making the interaction feel more human and less transactional.

The Heath brothers, who have written several books on the topic of communication, including “Made to Stick: Why Some Ideas Survive and Others Die” emphasizes the importance of using storytelling to make ideas memorable and engaging.

Use these ChatGPT prompts to build more memorable and engaging conversations with your prospects.

Prompt 5

Write a humorous cold email that incorporates storytelling, and you provide project management software. Reaching out to a potential customer. Pain Point: Difficulty with remote team collaboration.


Subject: A Tale of Remote Team Collaboration Woes

Hi [Prospect],

I heard a tale recently of a team that was struggling with remote collaboration. They had team members all over the world, and communication was a nightmare. They tried everything from carrier pigeons to smoke signals, but nothing seemed to work.

One day, they discovered a magical tool that changed everything. This tool allowed them to collaborate seamlessly, no matter where they were in the world. It was like they were all in the same room, except without the awkward small talk and stale donuts.

This tool is none other than [your product name]. It’s designed specifically for remote teams, and it will make your collaboration headaches disappear faster than a magician’s assistant.

So, are you ready to add some magic to your team’s collaboration? Let’s schedule a demo and make it happen.

[Your Name]

Prompt 6

Write a humorous cold email that incorporates storytelling. Reach out to a potential customer who owns a small business and struggles with keeping track of their finances. Offer them a financial management tool that can simplify their bookkeeping and accounting processes.


Subject: The Tale of a Small Business Owner and the Not-So-Scary Finances

Dear [Name],

Once upon a time, there was a small business owner who was scared of one thing: finances. Every time she opened her accounting software, she felt like she was entering a haunted house. The numbers were scary, and she always felt like she was in over her head.

But then one day, she met a financial management tool that changed her life. It was like a knight in shining armor that helped her slay her financial dragons. With just a few clicks, she could track expenses, manage invoices, and even generate reports.

Now, the small business owner lives happily ever after, without the fear and stress of managing her finances. And we want to share this fairy tale with you. Our financial management tool is the ultimate solution to your bookkeeping and accounting woes.

So, if you’re tired of feeling like you’re in a haunted house every time you open your accounting software, let us be your knight in shining armor. Let’s simplify your financial management tale and make it a happy ending.

Best regards,
[Your Name]

Prompt 7

Write a cold email promoting a social media management tool, but tell a humorous story about a time when social media backfired on you or someone you know, and how the tool could have helped avoid the situation. Make the story engaging and relatable to the reader.


Subject – A social media disaster

Have you ever had a social media post that you regretted immediately after hitting “send”? I certainly have! 

One time, I posted a photo of my cat in a cute outfit, but I accidentally tagged the wrong company instead of my friend who was supposed to see it. Let’s just say, the company was not amused.

With [Product], you can schedule your posts in advance, avoid embarrassing typos, and even track your analytics. It’s like having a personal assistant for your social media!

Let me know if you’re interested in learning more.

[Your Name]

3. Wordplay

Wordplay can be an enjoyable and effective way to grab a potential customer’s attention in your communications.

It involves using puns or clever phrases to emphasize your point and keep the reader engaged.

For instance, a catchy subject line like “Working hard or hardly working? Our tool can help” could be an excellent approach to capture someone’s interest.

By combining humor, creativity, and linguistic flair, wordplay can be a compelling tool for establishing connections and promoting your ideas or products.

When using wordplay in a cold email, it’s important to strike the right balance between being clever and being clear. Note the following points before using wordplay in your emails,

  • Know your audience – Wordplay can be tricky, so it’s important to know who you’re communicating with and what language will resonate with them.
  • Use humor appropriately – Humor can be a great way to break the ice or grab someone’s attention, avoid using humor that is inappropriate, offensive, or in poor taste.
  • Test your messages – Just like with any other cold email campaign, it’s important to test different variations of your subject lines and messages to see what works best. 
  • Keep it brief – Wordplay can be a great way to spice up your email subject line or opening, but it’s important to keep the rest of your email focused and to the point. 

Check out these chatgpt prompts to discover ways to incorporate wordplay in your emails –

Prompt 8

Write a humorous cold email that wordplay, and you provide marketing automation software. Reaching out to a potential customer. Pain Point: offer your all-in-one automation platform.


Subject: Don’t Be a “Multi-Tool” Victim – Get All-in-One Automation!

Hello [Name],

Are you tired of juggling multiple tools to manage your marketing campaigns, only to end up with a messier-than-ever CRM and ATS? It’s like trying to play a game of Jenga, but instead of blocks, you have to balance tools and data, and it’s not nearly as fun.

But fear not, because [Product Name] is here to rescue you from being a “multi-tool” victim. Our all-in-one marketing automation platform will streamline your workflow, saving you time and hassle. Plus, with our easy-to-use interface, you won’t need to be a tech whiz to get started.

Don’t let manual updates drag you down. Let our marketing automation tool help you jumpstart your success. Want to see it in action? Let’s automate a demo!

[Your Name]

Prompt 9

Write a cold email as a salesperson promoting a writing tool, but include a pun in your message about the importance of good grammar.


Subject line: Don’t comma-nd me!

Hey [Prospect],

Are you tired of second-guessing your writing skills and constantly questioning if you’ve used that comma in the right place? It’s time to put an end to those woes and say hello to our writing tool!

With our tool, you can confidently create masterpieces that will have your readers hooked from the first sentence. No more comma-kaze, confusing homophones, or dangling modifiers – our tool will ensure that your writing is error-free and engaging.

Trust us, your readers will thank you for it. So why wait? Sign up now and take your writing to the next level!

Best regards,
[Your Name]

Prompt 10

Compose a cold email promoting a customer relationship management tool, but use a clever turn of phrase to highlight the benefits of keeping in touch with customers. Pain: missing out on opportunities because of managing customers in Excel or google sheets.


Subject – Keep your customers close and your CRM closer

Hi [Prospect],

Do you feel like you’re missing out on sales opportunities because you’re struggling to keep track of your customers? Are you tired of trying to manage your customer relationships in Excel or Google Sheets?

You need a CRM to keep all your customer information in one place, so you never miss an opportunity again. 

As the old saying goes, “out of sight, out of mind.” Don’t let your customers slip through the cracks. With our CRM tool, you can keep your customers close and your sales closer.

Don’t let outdated methods hold you back. Let us help you take your customer relationships to the next level.

[Your Name]

4. Self-mockery

Self-mockery can be a great way to create a humorous tone in a cold email while also showing a bit of vulnerability.

Here are a few important things to keep in mind when you self mock in your cold emails –

  1. Be authentic – Don’t try too hard to be funny or self deprecating. 
  2. Keep it lighthearted – The aim of self-mockery is to generate a lighthearted and amusing tone in your cold email without making yourself the target of the joke. Therefore, it’s essential to maintain a positive and light tone throughout your email.
  3. Tie it to the purpose of the email – Make sure that your self-mockery ties back to your product or what you want to convey in the cold email in a clear and meaningful way.

Prompt 11

Imagine you are a salesperson selling a meeting scheduling software. Write a hilarious cold email that involves making fun of yourself in a lighthearted way. 


Subject: A bad joke and a good software

Hey [Prospect],

I have to confess something. My jokes are terrible. Like dad-joke level terrible. But don’t worry, I won’t bore you with them.

Instead, I want to tell you about our software. It’s user-friendly and will help you schedule meetings in a snap. Plus, it’s so efficient, you’ll have more time to tell your own bad jokes (or good ones, if you’re one of the lucky ones).

If you’re interested, I’d love to schedule a demo and show you how our software can make your life easier. And don’t worry, I promise to keep the jokes to a minimum.

[Your Name]

Prompt 12

Write a cold email as a salesperson selling a language learning app, but with a twist – make fun of yourself in a lighthearted way.


Subject: Learn a new language (even if I can’t)

Hey [Prospect],

Before you think I’m a polyglot, let me clarify: I’m not. I’m more of a “bonjour-hola-ciao” kind of person.

That being said, [Your Product] is a perfect app for people like me who need a little extra help with language learning. 

It’s user-friendly and comes with a range of features to make learning fun and engaging, from interactive lessons to language exchange communities. Plus, it’s affordable, so you won’t break the bank while you learn a new language.

If you’re interested, let me know, and I promise to brush up on my language skills before I give you a personalized demo.

[Your Name]

Prompt 13

Assume yourself as a salesperson and write a self-mockery involving cold outbound email selling time management software to a prospect who is also a salesperson like you.


Subject: Time is Money (But Let’s Be Real, I’m Always Running Late)

Hey [Prospect],

I hope this email finds you well, and that you’re not buried under a mountain of tasks (like I often find myself).

As a fellow salesperson, I know that time is one of our most precious resources. But sometimes, it can feel like there’s just not enough of it to go around.

That’s why I’m excited to introduce you to [Software Name], a time management software that’s so easy to use, even I can manage it (and trust me, if I can do it, anyone can).

As someone who’s struggled with time management in the past, I can personally vouch for the effectiveness of [Software Name]. It’s been a game-changer for me, and I know it can be for you too.

If you’re interested in learning more, I’d be happy to set up a demo and walk you through all the features. Just let me know, and we’ll find a time that works for you.

[Your Name]

5. Observational humor

Observational humor is a type of comedy that takes everyday situations and finds humor in them. It’s often characterized by witty comments, clever one-liners, and unexpected observations about the world around us.

When it comes to writing cold emails, incorporating observational humor can be a powerful way to engage your reader and make your message more memorable. Here are some tips on how to incorporate observational humor into your cold emails:

  • Start by identifying a relatable situation or experience that your prospect may have encountered. This could be something like the challenges of remote work, the frustration of dealing with overflowing email inboxes, or the struggle to stay productive while working from home.
  • Once you’ve identified the situation, try to find the humor in it. What are some unexpected or amusing aspects of the situation that you can point out? What are some clever or witty observations you can make about it?
  • Use your humor to build a connection with your prospect. By acknowledging the challenges they’re facing and finding a way to laugh about them, you’ll be able to build rapport and make your message more engaging.
  • Make sure to keep it light and positive. The goal of observational humor is to create a sense of lightheartedness and fun, not to offend or upset your reader. So, make sure to steer clear of anything that could be taken as insensitive or inappropriate.

Prompt 14

Compose a cold email in which you promote marketing automation software to a potential customer. Try to inject some observational humor into your message by making a witty comment about the challenges of email marketing.


Hi [Prospect],

I hope this email doesn’t get lost in the sea of messages flooding your inbox. As a fellow salesperson, I understand the pain of email marketing. It can feel like trying to find a needle in a haystack – but with our marketing automation software, you’ll be able to find that needle with ease.

Our software can help streamline your email campaigns, increase engagement rates, and even automate follow-up emails. Plus, you’ll never have to manually send another email again!

Let’s schedule a quick call this week to discuss how our software can benefit your business. Trust me, your inbox will thank you.

[Your Name]

Prompt 15

Write a cold email as a salesperson promoting a collaboration tool to a potential prospect, but try to incorporate an observational joke about the difficulties of remote teamwork to add some humor to your message.


Hey [Prospect],

Does collaborating with your remote team feel like a twisted mess? It’s like trying to do yoga poses while holding a laptop, and it’s not pretty.

But don’t worry, our collaboration tool can help you and your team work together with ease. Say goodbye to twisted limbs and hello to seamless communication, file sharing, and real-time collaboration.

Let’s set up a call so I can show you how our tool can make your life a little less awkward and a lot more productive. No yoga mat required.

[Your Name]

Prompt 16

Compose a cold email promoting a productivity tool, but add an observational joke about the difficulties of working from home to make the email more engaging.


Subject: Get More Done While Wearing Sweatpants

Working from home has its perks (no commute, pajamas all day), but let’s face it, staying productive is a whole different ball game.

The distractions are endless: a cat who won’t stop meowing, a dishwasher that needs unloading, or that never-ending pile of laundry staring at you from the corner of your eye.

That’s where [Productivity Tool] comes in. Our tool will help you stay focused, organized, and on top of your work, no matter what life throws your way. Whether you’re battling your cat for your keyboard or drowning in laundry, our tool has got your back.

Let’s schedule a demo so I can show you how [Productivity Tool] can help you get more done, even in your comfiest sweatpants.

[Your Name]

Suggested read: 30 tried and tested chatgpt prompts for sales outreach

Final Thoughts

In a world where cold emailing can be tedious and ineffective (sometimes), adding a touch of humor can make all the difference. 

With the help of these witty and humorous chatgpt prompts, you can create emails that not only catch the reader’s attention but also make them more likely to respond positively.

Remember, the key is to keep your jokes light, positive, and always on-brand.

With a little bit of creativity and good humor sense in your chatgpt prompts, you’ll be surprised at how effective and enjoyable cold emailing can be. So go ahead, give it a shot, and let the laughter and sales roll in!