How to Write Hilarious Cold Emails That Get Opened, Read, and Replied To

Does sending cold emails make you frown? Well, turning that frown upside down with humor can lead to more sales smiles.

A healthy dose of comedy in your outreach makes your messaging stand out and stick in prospects’ minds. Laughter releases feel-good endorphins that stimulate relationship-building. Amusing emails also grab attention in crowded inboxes, increasing engagement.

But random cornball jokes won’t cut it. Effective humor requires strategic planning and flawless delivery. Read on to master the art and science behind funny, conversion-driving cold emails. This comprehensive guide reveals proven tips toResearch Your AudienceUnderstand CulturePersonalize Your HumorBalance Jokes & ProfessionalismWrite Catchy Subject LinesStructure Engaging EmailsUse Tools to OptimizeAnd more!

With the right skills, your witty words will woo and wow recipients all the way to your calls-to-action. So break out your knock-knock jokes and get ready to ROFL…and sell!

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Why Use Humor in Your Cold Emails?

Cold emailing can often feel like shouting into the void. Your inboxes are crowded with boring pitches that rarely get opened, let alone generate replies. So how can you make your outreach stand out? The answer is humor.

Adding strategic humor to your cold emails can help you break the ice, grab attention, boost engagement, and make yourself memorable. Let’s explore the main benefits of using humor during prospecting outreach:

Break the Ice and Build Rapport

Cold emails come from strangers out of the blue. Humor helps humanize you and builds an initial connection. An amusing quip related to their industry or interests shows you did your research on them. This makes you seem friendly, not just another robotic sales pitch.

Humor also relieves tension and awkwardness from approaching someone cold. An icebreaker joke eases both parties into the interaction. Laughter literally releases feel-good endorphins that stimulate bonding. This chemistry makes the recipient more receptive to your outreach.

For example, pretend you find the prospect’s social media photo at a conference for “Acme Products”. You could say:

Subject: Did you grab one of those Acme anvils at the conference? 

Hi [Name],

I saw your photo from the big Acme Products conference. I hope you grabbed one of those free anvils! You never know when you'll need to drop one on a coyote.

All jokes aside...[continue pitch]

This personalized humor acknowledges you did your research on them. It also references pop culture they likely understand, acting as an “inside joke” between you two.

Grab Attention and Improve Open Rates

Humor grabs attention in crowded inboxes. Most pitches are dry and formal. A quirky, funny subject line intrigues recipients and tempts them to open it.

Studies show including humor in subject lines can increase open rates by 15% or more. The laughter triggers an immediate emotional response that cuts through the noise.

For example, pretend you are selling project management software. A funny subject line could be:

Subject: Let's tie up those "loose ends" 

Hi [Name], 

You seem to have a "project" finding the right project management solution. I think our software would be the perfect "task" to get you organized. Let's jump on a call to discuss how we can prevent any more "hang ups" in your workflow...

Here, the punny subject line grabs attention and conveys the topic in a memorable way. The body continues the light humor related to the product pitch.

Increase Engagement, Replies, and Conversion Rates

Humor boosts engagement metrics like open rates, click rates, and replies. Emotion drives action, and laughter creates positive feelings.

In one study, funny emails saw open rates of 70%, compared to more serious messages at 50%. The greater engagement leads to more qualified leads.

Humor also makes your own brand more likeable. In a crowded market, personality goes a long way. As people enjoy your emails, they develop a favorable impression of your product. This increases conversions compared to stiff, overly salesy language.

Consider this starter email for a CRM tool:

Subject: Let's take this relationship to the next level

Hey [Name],

I hope you don't think this is moving too fast...but I saw your company and thought we'd be the perfect match! My CRM tool is the best way to manage all your customer relationships in one place. Never forget an important date or deal again! 

If you're ready for that long-term commitment, let's have a quick video call to see if we're the right fit for each other. Think of it like a first date before we make it "official." Looking forward to connecting!

[Your name]

Here, playful analogies like a first date make the sales pitch more human versus formal. The recipient is more likely to “match” with your likeable brand.

Make Yourself Memorable and Likeable

Humor also makes YOU more memorable as a sender. Forgettable content blends into the masses. But a witty, chuckle-worthy email will stick in someone’s mind for days.

In the same vein, comedy makes you seem fun, friendly and approachable. Recipients appreciate a well-timed laugh rather than just feeling “sold to.” They’ll look forward to your future emails to see what clever things you’ll say next.

Pretend it’s New Year’s Day, and you sell consulting services. You could say:

Subject: My New Year's Resolution is to Help Your Business 

Happy New Year [Name]!

I hope you're not too hungover today to read this email. While you were out partying, I was making New Year's resolutions about how to grow my consulting business. 

My top resolution is to provide awesome marketing advice to companies like yours. I think we'd make a great team in 2023. Want to grab coffee next week and toast to a prosperous new year together? The first round is on me!

[Your name]

The timely, festive humor builds rapport. The prospect feels goodwill towards you and is more likely to meet over coffee. A dry pitch would not evoke the same positive reaction.

In summary, strategic humor makes your cold outreach stand out and succeed. A bit of comedy can break the ice, get opened, increase engagement, and boost brand sentiment. With so many benefits, it’s worth testing funny messaging and subject lines in your next campaigns. Just ensure humor aligns with your brand voice and avoid anything potentially offensive. With some practice, you’ll find humor to be a powerful email strategy.

Know Your Audience and Their Sense of Humor

Humor is subjective. A joke landing with one person may completely flop with someone else. Before injecting humor into cold emails, research your target audience and what makes them laugh. Tailor your comedy to resonate with their sensibilities.

Research Their Demographics Like Age, Location, Job Title

Demographics like age, gender, location, education level, and job title influence humor preferences. Observe patterns in what comedy your audience responds best to.

For example, younger audiences may appreciate memes, emojis, gifs, and pop culture references. Using a meme about social anxiety could appeal to millennial tastes:

Subject: This is my brain overanalyzing before sending a cold email

[Insert gif of cartoon character overthinking]

Hey [Name], 

My mind races before sending ANY cold email. "What if they think I'm weird?" "What if I said something dumb?" Don't worry, I took some deep breaths before hitting send on this one!

But seriously, I saw your company [detail research here] and think you'd be a great fit for [solution]. Want to see if I'm right?

Let me know if you have 20 mins for a quick call. Talk soon!

[Your name]

Meanwhile, more mature audiences may find memes juvenile. Puns, witty remarks, and cultural references suit them better. Consider this subject line for baby boomers:

Subject: Our tool will have you walking on sunshine!

Hi [Name], 

You're probably sick of annoying software that makes you grumble "Looks like we've got another case of the Mondays." Well, our intuitive platform will give you a reason to exclaim "Hallelujah, it's Friday!" 

In all seriousness, our decades of experience creating business solutions will bring nothing but sunny skies to your workflow. Let's connect to see if we're a match made in heaven!

[Your name]

The retro song and Office Space references appeal to older generations familiar with that comedy. Know your audience’s age tendencies and use appropriate humor.

Look for Clues in Their Social Media Profiles

Research social media profiles for clues on recipients’ interests and what comedy may land. Posts about favorite TV shows, hobbies, family, vacations, etc reveal personalities you can incorporate humor around.

If their Instagram shows photos from an African safari, you could say:

Subject: Hope you didn't meet an elephant afraid of mice! 

Hi [Name],

I saw photos of your awesome African safari on Instagram. How amazing! I've heard elephants there have no natural predators...except mice. (At least according to cartoon documentaries I've seen.)

On a related note, here's an idea that's not "mousing" around...[your pitch]. Since you like adventures, let's set up a meeting to explore if we're the right fit!

Let me know some times that work for you.

[Your name]  

The personalized joke about their trip grabs attention. Tailor humor per social media instead of generic templates.

Consider Differences in Cultural Humor

Humor also varies across cultural backgrounds. American readers may not understand jokes referencing cricket if their background is Chinese. Adapt jokes to what different cultures find funny.

For a company in Germany, discuss football instead of American football analogies. For prospects in India, use cricket versus baseball metaphors. Do research on what makes different cultures laugh.

This example suits a Korean prospect:

Subject: Our tool is as reliable as dak-galbi delivers 

Hi [Name],

I came across your company and thought our software would be as perfect of a match as dak-galbi chicken and rice cakes! Our tool will spice up your [their field] as much as that savory Korean dish will spice up your taste buds.

Let's set up a quick call to start this beautiful friendship off right. I'll bring the kimchi :) Looking forward to speaking!

[Your name]

The food analogy resonates with their background. Humor should reflect knowledge of the culture’s tastes.

Test Different Humorous Approaches in A/B Tests

Test humor styles in A/B testing campaigns. Try personalized jokes about their social media in one. Use self-deprecating humor in another. See if observational humor works better than wordplay puns.

Track open rates, replies, and conversions for each version. Double down on approaches that perform best. Keep honing your skills for that perfect comedic touch.

In summary, appeal to your recipients’ demographics, cultural background, and interests when incorporating humor. Research thoroughly and test out different comedy angles. With practice, your witty cold emails will soon have them ROFL…and hitting reply!

Best Practices for Writing Funny Cold Emails

Crafting humorous cold emails is an art. Master these proven tips to make recipients laugh while still projecting professionalism.

Use Personalized Humor Based on Their Interests

Generic jokes come off as low effort. Personalized humor shows you researched them and appeals to unique interests.

Their social media reveals passions to incorporate like favorite sports teams, TV shows, hobbies, etc. If their Instagram has travel photos, you could say:

Subject: Let's connect before your next adventure!

Hi [Name], 

I loved the pics from your Hawaii trip! That beach looks way more fun than sitting at my desk. Hopefully this email will brighten your day like those vibrant sunsets you posted.

But I also noticed your company [detail research here]. I think [your solution] would be the perfect fit to help you tackle [their problem]. Want to chat and see if you agree?

I'm free on [days] this week. Let me know what works!

[Your name]

This personalized touch builds rapport quickly. Get creative linking their interests into pitches.

Tell Short, Engaging Stories with Witty Humor

Brief, entertaining stories engage readers more than dry stats. Plant humor into anecdotes relevant to your product or their pain points.

If you sell project management software, you could say:

Subject: The case of the messy project

Hello there,

Let me tell you the curious case of a team that lacked project oversight. They were working on a highly complex project involving quantum teleportation (you know, casual stuff). 

Without PM software, their project was pure chaos! Deadlines were missed, tasks were confused, and our team hero Jane was at the point of tearing her hair out. But then they discovered [your tool]! Order and sanity were restored. The project finished on time, and Jane kept her lovely locks intact. 

So, if your projects resemble a hairy situation, our software can help! Let's...

This engaging story seamlessly flows into the pitch. Sprinkle in humor but keep stories concise.

Sprinkle in Clever Wordplay and Puns

Puns surprise readers with an unexpected play on words. Clever phrases capture attention in subject lines or opening lines.

For email security software:

Subject: Don't be phished in!

Hey [Name],

Have you been hooked by phishing scams? As the old saying goes, "There's plenty of phish in the sea." Well we have the lure to reel in those cyber scoundrels! Our security prevents breaches by hackers trying to bait and catch your data. Let's schedule a chat to reel in...

For a coffee brand:

Subject: Our coffeebeans bring all the productivity to the yard 

Hi [Name], 

People say our coffee is "grounds" for your workday productivity. The rich flavors provide the "perk" you need to excel. Don't "espresso" your doubts - our beans truly deliver. Let's connect over how we can "roast" your competition with peak energy levels. Does a virtual coffee break work?

Looking forward to it!
[Your name]

Sprinkle in playful language, but avoid overdoing it. Wordplay works best briefly.

Use Self-Deprecating Humor Appropriately

Poking fun at yourself or industry shows humility. But keep it light, not sad. Stay upbeat and positive.

For an accounting platform:

Subject: This accounting software won't make you fall asleep!

Hi [Name], 

I get it - talking accounting is not as fun as talking puppies. But I promise this won't be a snore fest! Our software makes managing finances easier than binge watching Netflix...okay maybe not THAT easy, but you get the idea. Let's have a lively discussion about how we can improve your accounting woes. I've got the coffee ready to brew!

Let me know when works. This accountant promises to bring the laughs...

[Your name]

Gently poke fun at “boring accountant” stereotypes, while keeping things cheerful.

For a sales CRM:

Subject: Let's crush quotas...but I'll probably still miss mine

Hi [Name], 

As a fellow salesperson, I get the pressure of hitting quotas. Some months it seems like I have a better chance of going to the moon than hitting my number! But with [Your CRM], I can get organized to develop my pipeline and close more deals. Want to hear how we can meet those elusive quotas together? I'll bring the celebratory champagne just in case!

Let me know when you're free for a call. Talk soon!

[Your name]

Make light jokes about shared sales struggles. Self-deprecating humor builds camaraderie.

Make Observational Jokes About Shared Experiences

We all face similar problems in business like slackers, pointless meetings, tech issues, etc. Use observational humor about these shared experiences.

For example:

Subject: Let's make the most of your next useless meeting

Hi [Name],

Don't you love when you get invited to vague meetings with no agenda? I like to play meeting bingo: "Any questions?" *bingo square* "Let's circle back" *bingo again!*

But instead of just surviving boring meetings, our [meeting software] can make them productive. Set clear objectives, time limits, action items and more. Take back your precious time!

Want to have an actual effective meeting about improving meetings? Let me know when you're free.

[Your name] 

Make funny remarks about problems we universally face in business. It bonds you with the reader.

Balance Humor and Professionalism

Humor helps messages stand out, but don’t lose sight of your goals. Follow comedy with concise, professional pitches.

For example:

Subject: Let's get cookin' on a winning marketing strategy!

Morning Andrea,

I hope your week is off to a good start! I saw that your restaurant, Chez Andrea, landed #1 on Yelp's Top 100 list - how amazing! You must have the secret sauce for delighting customers. 

As a digital marketing whiz, I'd love to cook up ways to keep growing Chez Andrea's 5-star reputation. My team specializes in social media marketing, email campaigns, SEO, and more. 

Want to set up a time to brainstorm promotions as tasty as your signature 87-layer lasagna? I'm excited to collaborate to keep Chez Andrea the hottest spot in town!

[Your name]  

The food humor fits for a chef. But the pitch stays focused and benefit-driven.

Be Authentic and Avoid Anything Offensive

Most importantly, ensure humor aligns with your brand voice and values. Never include jokes that could offend. Skip profanity, politics, religion, sex, stereotypes or self-bashing. Keep things light, clean, and safe for work.

In summary, personalized humor, stories, wordplay, self-deprecation, and observations make effective email comedy. Balance jokes with concise professionalism to build connections, while also moving deals forward. With some finesse, your witty emails will have your stats laughing all the way to the bank.

Subject Line Ideas for Humorous Cold Emails

Crafting witty subject lines piques interest and drives opens. Include humor through references, exaggeration, questions, wordplay, or observations.

References to Pop Culture or Current Events

Tie subject lines to what’s currently trending in pop culture or news. This timely humor makes you seem “in the know” on their interests.

For example, a subject line around a viral meme:

Subject: Do you like bread? 

Hi [Name],

I'm sorry to bother you with the silliest question ever. Do you like bread? I only ask because I saw your company [detail research] and think our solutions would be a perfect pairing, like bread and butter. [Continue pitch]

Let me know if you're open to a quick call to discuss!

[Your name]

The reference capitalizes on that meme’s popularity.

For a current hot TV show:

Subject: Is your marketing strategy squid game level?

Hi [Name], 

I've been bingeing Squid Game recently and it got me thinking - is your marketing strategy ruthless as the show, or still a little soft around the edges? If it's the latter, I think [Your Tool] can elevate you to top-tier, survive-or-die marketing boss status. Let's grab a call to see if you'd be the winner in a marketing face-off!

Looking forward to chatting,
[Your name]

Linking to the latest shows builds common ground. Stay on top of trends.

Exaggerated Claims or Compliments

Subject lines with exaggerated adjectives stand out for their bold promises or flattery. This humorously confident tone intrigues readers.

Subject: Our tool will absolutely, positively change your LIFE

Hi Andrew, 

You're probably thinking, "That's a pretty bold claim!" I know, I know, it sounds like classic sales hype. Buuuut I genuinely think our tool is the most brilliantly, stupendously efficient solution for your needs. Ready to hear why?

Let's chat soon!
[Your name]

Starting strong, if hyperbolic, grabs their attention.

Flattering them also works:

Subject: You're an [industry] rockstar!

Hi [Name], 

I came across your marketing work for [Company] and wow - you're an absolute rockstar! The way you [detail impressive work] proves you have some serious skills. As a fellow marketing guru, I'd love to brainstorm how we can collaborate...

Just don’t lay it on too thick. Sincerity wins over slimy flattery.

Quirky Questions or Calls to Action

Asking a funny question or call to action prompts engagement. Curiosity leads them to open the email.

For example:

Subject: Quick you like money?

Hi there! 

I know this is a strange question, but do you enjoy having money? Like, green cash filling up your bank account? 

Because that's exactly what our services provide ;) [Continue pitch showing ROI]

Let me know when you're free for a quick call...

Or a funny call to action:

Subject: Scratch and sniff this email for a pizza treat!

Hi [Name],

I've invented a new technology that allows me to send scent through email. Just scratch your screen and take a whiff...smells like delicious cheesy pizza, am I right??

Now that I have your attention with phantom pizza smells, here's my actual pitch: [continue...]

Get creative with unusual questions and commands that entice opens.

Play on Words Related to Your Industry

Clever wordplay related to your industry or product sets a humorous tone. Stay on brand with puns tailored to the reader.

For example, for accounting software:

Subject: Our tool will be the CFO of your dreams

Hi [Name],

I know accounting puns must make you groan, but this one deserves a chuckle...Our software provides insights that would make even the most meticulous CFO proud. Let's connect over how we can have you grinning about your finances again.

Looking forward to speaking!
[Your name]

For a construction company:

Subject: Our tools will have your competition cowering

Hello [Name], 

When it comes to top-notch construction equipment, we NAILED it. Our tools and machinery will have your competitors running for the hills. Let's chat about how our solutions can revolutionize your business. I know you'll dig what we have to offer!

[Your name]

Industry-specific puns show your expertise in their field.

Witty Observation About Their Business

Finally, make humorous observations about something on their website to grab attention.

For example:

Subject: Nice website photo! You really make spreadsheets look cool ;)

Morning Natasha! 

I checked out the Acme Accounting website, and I must say, you make spreadsheets look WAY more interesting than I thought possible. I don't know how you make calculating numbers look so cool, but kudos! Of course, I'm sure our automation software could save you a few tedious spreadsheet hours. Want to chat?

Let me know when you're free for a quick video call. Looking forward to it!

[Your name]

Compliment an aspect of their site to start positive. Then politely pitch your solution. Witty observations create a customized feel.

In summary, capitalize on trends, exaggerate, ask questions, use wordplay, or point out details from their digital presence. Combine these tactics with your industry expertise to craft amusing subject lines that spark action.

Email Body Ideas for Humorous Cold Emails

Grabbing attention with a funny subject line is just the first step. Craft an engaging email body keeping the humor flowing towards your pitch and call-to-action.

Opening with a Lighthearted Personal Anecdote

Share a brief, humorous anecdote to start conversations casually. Keep it relatable to build connection.

For example:

Hi [Name],

The other day, I grabbed coffee with a friend who owns a yoga studio. I figured yoga would be a relaxing break from my desk. Well, 50 minutes later I stumbled out of there more sore than relaxing! Let's just say crow pose did not leave me floating on a cloud of zen. 

Speaking of struggling businesses, I noticed your shop [detail research here] has room for growth. Based on your website, I think [Your Solution] could be the perfect fit to ease some of your marketing headaches, even more than yoga helps my sore muscles!

Would you be open to a quick video call this week? I'd love to demonstrate our platform and see if it's something that could help you.

Looking forward to speaking!
[Your name]

The funny anecdote bonds you as fellow small business owners. Segue smoothly into your pitch.

You could also reference a relevant news event:

Hi [Name],

Did you catch the news about the lucky winner of that $1 billion lottery jackpot last week? It got me daydreaming about how I'd spend that fortune! A private island would be nice. But I'd probably hire Elon Musk to build a rocket ship so I could take an orbital space vacation. 

Then my mind wandered back to reality - and how I could help hardworking companies like yours find success without stumbling upon a billion dollars. I noticed [detail research] and think our service could help take your business revenue to new heights! Would you be open to a quick call?

Let me know a few times that work for you. Talk soon!

[Your name]

Briefly share the funny daydream before pivoting professional.

Telling a Funny Story Relevant to Your Product

Share a short, entertaining story that relates to your offering. Sprinkle humor in while showcasing the benefits.

For example:

Hi [Name],

Picture this: It's Monday morning. I'm sipping a delicious vanilla latte on my way to a big client meeting. Feeling fresh and prepared, with my laptop and presentation ready...when suddenly disaster strikes! My laptop blue screens, refusing to turn back on! All that preparation for nothing. I arrive at the meeting with some crumpled printouts and have to awkwardly explain why my laptop crashed. Needless to say, we did not get that contract.

If only I had [Your Software]'s automatic cloud backups! All my work wouldn't have disappeared into the abyss. I never made that mistake again. So if you want to avoid awkward tech failures like me, our platform has your back. Let's schedule a quick video walkthrough so I can show you how we can make technology mishaps extinct!

Looking forward to speaking,
[Your name]

Entertain them, but keep the story tight and beneficial.

Using Humor When Acknowledging Sales Pitch

When delivering your pitch, poke fun at sales stereotypes in a friendly, subtle way. This builds rapport and makes you seem authentic.

For instance:

Hi [Name], 

Let me start with full transparency - this is a sales email. I know, cue the eye rolls. But I promise not to subject you to cheesy sales slogans or over-the-top claims about how our software will change your life. 

Here are the facts: I came across your [Detail Research], and think our tool could significantly streamline X. You seem like a savvy business owner, so I'd love to simply discuss the facts over a quick call and get your candid opinion. No hard sales pressure, just an open and honest chat.  

Does jumping on a 30 minute call sometime this week work for you? Let me know what time works best.

I look forward to speaking!
[Your name]

Preemptively handling sales skepticism helps build trust.

Self-Deprecating Joke About Own Skills or Industry

Use tasteful self-deprecating humor highlighting your flaws or industry stereotypes. Avoid negativity, but light jokes build affinity.

For example:

Hi there,

As a fellow entrepreneur, I know how hard it is to keep up with the ins and outs of accounting. I'm mathematically challenged myself - I still occasionally count on my fingers! But thankfully our easy accounting software helps me keep finances straight. 

I noticed your store [research detail] could also benefit from our intuitive platform. Let's connect to explore how we can help each other stay sane while running all the aspects of a business! 

Let me know when you're free for a quick call. Have a great day!

[Your name]

Poking fun at poor math skills makes you relatable.

Or stereotypes about your industry:

Hi [Name], 

Let me guess - when you hear "pharmaceutical sales rep", you think of some pushy guy in a tacky suit, right? I can't blame you, we don't have the best rep. 

But I promise I'm not that stereotypical salesperson. I genuinely want to help your medical practice by [detail value props]. I'd love to have an honest, no-pressure conversation about how we can work together. What do you think?

Hope to speak soon,
[Your name]

Address stigmas politely and tactfully. A little self-deprecation goes a long way.

Observational Humor About Shared Problems

Bond over common experiences in business we can all relate to and poke fun at, like useless meetings or overwhelmed inboxes. Using this observational humor makes you seem in-the-know on their world.

For example:

Hi [Name],

Let me guess - you're joining this meeting from a tiny closet with piles of paperwork surrounding you? My "home office" isn't much better. There's something about remote work that makes closets and laundry rooms seem like an appealing workspace! 

But imagine how much more productive we could be with [Your Software]. Our collaboration tools bring organization to the chaos of remote teams. Set up a quick demo with me so I can show you how our platform can make working from your closet suck a little less!

Let me know when you're free,
[Your name]

shared understanding builds instant connection. Look for common gripes in their field.

Funny Wordplay Leading Into Key Points

Sprinkle your pitch with playful turns of phrase, rhymes, or alliteration. This keeps your message memorable while highlighting benefits.

For example:

Hello [Name],

I came across your lovely flower shop, and I'd like to help it bloss-om with some fres-hened up digital marketing! Our SEO strategies are pollen-ting with potential to attract local customers. We'll plant your shop at the top of search so you can weed out the competition!

More seriously though, I'd love to discuss how our targeted SEO and Google Ads services connect more local buyers with your floral business. Let's set up a time to chat flowers, digital marketing, and more!

Looking forward to speaking,
[Your name] 

Playful floral wordplay keeps your pitch entertaining and stickier.

When done right, these email humor tactics attract, engage and convert. Combine different ideas in your own style to make prospects smile while also driving deals forward. A little laughter builds relationships that foster sales success.

Best Practices for Humor in Follow-Up Emails

The humor doesn’t stop after your first outreach. Follow-ups present more opportunities to build rapport through comedy, personalized jokes, compliments, and callbacks.

Callback Jokes to Initial Outreach

Referencing a laugh from your original email makes the recipient feel good. It also shows you remember small details about them.

For example, if your first email said:

I saw your team won the city softball championship - congrats! You must have the secret for bringing athletic success to the office. Let's chat about how we can also bring some all-star marketing to your winning team!

Your follow-up could be:

Hi [Name],

I hope you've basked in the glory of your epic softball championship victory! How will you celebrate? An office parade seems fitting ;)

I know you're busy on the heels of your win. But if you have time for a quick call about amping up your marketing with [Solution], I'd love to chat. Don't worry, I'll keep it short so we don't detract from your celebrations!

Let me know if you can squeeze in some time on your schedule. Talk soon!

[Your name]

Reminding them of the previous personalized joke shows your attention to detail.

You can also reference specific prospects you mentioned:

First email:

Hi [Name],

I see you're in the fashion industry. My friend Jenny just launched a clothing boutique too. Small world! I'd love to chat about how [Your Service] can help your runway shine.

Let me know if you have time for a quick call...


Hi again [Name],

I hope your week is going well! I chatted with my friend Jenny again about the challenges of starting a fashion business. It sounds like you both could benefit from [Your Offering]. 

Would you have time for a call later this week? I'd love to share some tips that can help your boutique take off just like Jenny's.

Looking forward to speaking!
[Your name]

Recalling specifics helps revive the previous connection.

More Personalized Humor Once Rapport Established

Once you have an existing relationship, incorporate humor reflecting your interactions so far. This strengthens bonds as you become more familiar.

For example, if you discussed the show Bridgerton:

Hi [Name],

Happy Friday! Any big Bridgerton binge watching plans this weekend? I have some tea - the new season comes out next month! 

I know we talked about how [Your Product] can help organize your workflow like a queen. Let's reconnect to discuss before you get swept up in the new drama! How about a call next week?

Looking forward to chatting,
[Your name]

Or a previous call:

Hi again [Name], 

I hope you survived the rest of our meeting without dozing off. I know discussing analytics is about as exciting as watching paint dry! But really important, of course.

Let's have a quick follow up call to recap action items and answer any other questions. Maybe we can liven it up by sending each other funny memes mid-meeting? I'm kidding about the memes (mostly). Talk soon!

[Your name]

Build on your shared experiences for inside jokes.

Humorous Compliments on Positive Replies

If they respond agreeing to a meeting or showing interest, send a funny thank you. Praise their “wise choice” to connect.

For example:

Hi again [Name],

Thanks for getting back to me! I'm looking forward to our call next Tuesday at 2pm. 

Wise choice to take me up on the meeting offer. I won't disappoint. In fact, I'll probably exceed your expectations and blow your mind with my marketing genius ;) 

I'll send over a calendar invite with the details. Have a great rest of your day!

[Your name]

Or if they shared positive feedback:

Hi [Name], 

I'm so thrilled to hear you enjoyed the trial of our software! Music to my ears. See, I knew you'd love it. My spidey senses rarely fail me when it comes to assessing top-notch clients.

Let's connect again soon to get your account all set up. Looking forward to helping your business ascend to new heights!

[Your name]

Celebrate positive replies with good-natured humor and praise.

Witty References to Previous Conversations

Finally, subtly referencing previous call takeaways or action items shows active listening.

For example:

Hi [Name],

I hope you've conquered that giant pile of laundry by now! Let's talk about getting [Important Action Item] in motion for you today.

Are you still free at 11:30? I'll send you a Zoom link shortly. Looking forward to diving in!

[Your name]


Morning [Name],

I hope your big presentation went well yesterday! Fingers crossed those last minute knife juggling practice sessions paid off ;)

Jokes aside, let's plan our follow-up to implement those marketing automation strategies we mapped out. How about next Tuesday afternoon?

Talk soon,
[Your name]

These small, personalized details reinforce relationships.

With a strategic dose of humor, your follow-up outreach keeps prospects engaged, while advancing deals towards conversions.

Avoiding Pitfalls When Using Humor in Emails

Humor boosts engagement, but implement it carefully. Avoid anything off-brand, controversial, overdone or unprofessional.

Ensure Humor Aligns with Brand Voice

Comedy should always align with your brand voice and values. Stick to the tone customers expect from you.

For example, a hip fast food chain can make edgy jokes a prestigious law firm could not. Know your audience.

If you’re known for being professional and polished, avoid risky humor like sarcasm or edgy gags. Stay true to your reputation.

Meanwhile, a casual start-up should skip stiff corporate jokes in favor of trendy memes and pop culture references.

Take this example of a mismatch:

Subject: Let's get litty on fleek!

How goes it dude! Let's get this money and secure the bag. HMU and we'll make your biz fleek AF! 

Stay woke,

This slang doesn’t suit a formal consulting firm’s brand. Ensure your comedy style aligns with customer expectations.

Steer Clear of Controversial Topics

Email is not the platform for controversial humor. It lacks the context of an in-person comedy club. Avoid topics that could offend, including:

  • Politics
  • Religion
  • Race
  • Gender
  • Sexual orientation
  • Disabilities
  • Age
  • Physical appearance
  • Culture

For example:

Hi [Name],

Did you catch the news about the presidential election? That [candidate] is so [offensive adjective]! What a nightmare. Let's hope someone with a brain can get elected next time!

Anyway, let's connect about how [Your Product] can help optimize your operations...

This may alienate prospects with contrasting views. Keep emails inclusive for everyone. Save risky material for private conversations once trust is established.

Don’t Overuse Humor and Dilute Your Message

A little humor goes a long way. Don’t overdo it to the point that your pitch gets lost.

For example:

Subject: Holy guacamole we should chat!

Top of the morning to you [Name]! Partaking in the delicious caffeinated nectar this AM? Nothing like a venti cold brew to jolt the senses, am I right?? 

Wow, it's getting awfully chatty in this email. Enough about coffee - let's talk soil! I saw your landscaping business is blossoming...get it, blossoming? Hehe. But in all seriousness, I think our tools could help your business grow even more...

Too much rambling humor buries the lead. Use it strategically in small doses.

Try the “3 humor touches” rule – a funny subject line, a joke in the opening, then one more quip in the body before getting down to business. Avoid letting humor highjack messaging.

Make Sure Humor Doesn’t Come Across as Unprofessional

While humor should sound human, avoid seeming too casual, flaky or silly. You want to come across as likeable yet still professional.

For example:

Subject: HEEEEYY let's do bizzzznass!

Whattup homeskillet! Your website is the bomb dot com! We gotta link up and do some bidnazz together, you feel me?? I'm hype to rap with you about our solutions nahmean? Let's crush it!

Peace outie homie!
[Your name]

This overly casual, slang-laden approach seems out of touch and unprofessional. Remember your audience and avoid crossing the line between fun and foolish.

Here’s another example:

Hi [Name],

Sorry for the slow reply - I was busy taking a nap under my desk when I should have been working! Haha, I'm so lazy sometimes. Anyway, we would love to partner with your company! Let me know if you want to get on a call sometime next rush at all. Talk to you whenever!

[Your name] 

Creating the impression of laziness or apathy damages credibility. While it’s fine to joke about common mishaps, don’t take it too far.

With mindful humor that enhances – not hinders – messaging, comedy strengthens your outreach. Avoid going off-brand, being insensitive, overusing jokes, or seeming foolish. With the right balance, humor drives leads without undermining professionalism.

Tools and Software for Writing Funny Cold Emails

Technology can help craft and optimize amusing outreach. Leverage these tools to more easily implement humor that converts.

Email Tracking to See What Resonates

Use email tracking software to see real data on what comedy styles perform best. This takes the guesswork out of what your audience responds to.

For example, track open and reply rates for:

  • Subject lines using different types of humor
  • Emails with memes vs gifs vs emojis
  • Self-deprecating jokes vs observational humor
  • Pop culture references vs current event jokes
  • Long form stories vs short one-liners

The metrics will show what joking lands and what falls flat. Double down on proven humor that generates engagement.

Tools like Yesware]( and [Mailtrack provide robust email tracking with things like:

  • Open and reply rates
  • Click tracking on links
  • Email forwarding data
  • Lead score based on engagements

Savvy use of metrics will optimize humor over time.

Email Templates With Replaceable Fields

Leverage email template tools to easily personalize humor at scale. Build a template once, then swap in custom details for each prospect.

For example, create a template with fields for:

  • The prospect’s name
  • Their company name
  • A recent news headline
  • Their industry
  • A personalized story

Then mix and match that customizable content with your humor framework:

Hi [Name], 

Did you see [News Story]? It really makes you think! On an unrelated note, I noticed your company [Company] seems to be having some challenges with [Industry Struggle]. I totally get it - I have a friend in [Industry] and she struggles with that too. One time she tried to [Funny Anecdote About Problem]!

Anyway, I think [Your Service] could really help improve your [Industry Struggle]. Want to grab a quick call to discuss?

Looking forward to hearing back!
[Your Name]

Tools like Woodpecker]( and [SalesHandy provide templates with merge fields to scale personalized humor.

Tools Like Phrasee for Data-Driven Subject Lines

Let data guide your subject line humor with tools like Phrasee. Their AI analyzes your past subject lines and results to recommend new options balancing humor, personalization, and optimization.

After inputting your data, Phrasee may suggest subject lines like:

Sarah, I saw your hilarious Instagram cat video 😹 - Let's chat marketing!

Hey Alex, you like Seinfeld right? Let's grab coffee and discuss [product]

Jane, imagine if optimizing [thing] was as easy as pie 🥧 - call?

The tool combines engaging humor and personalization optimized by past performance data. This takes the guesswork out of catchy subject lines.

Grammar Checking to Avoid Errors When Using Humor

While humor should have a conversational tone, make sure typos and grammar errors don’t undermine professionalism.

Tools like Grammarly proofread emails to fix:

  • Spelling mistakes
  • Punctuation errors
  • Broken sentence structure
  • Subject-verb disagreements
  • Run-on sentences

Proper grammar keeps your humor polished. It also prevents misunderstandings from readers taking errors literally.

For example, an incorrect autocorrect in a sales pitch could look silly:

Hi there, 

I scream your service could really help reduce churn. Let's chat flavors - I mean, factors - contributing to cancellations. Looking forward to speaking!

[Your name]

Clean up writing with a grammar checker before sending amusing outreach.

In summary, technology helps perfect humor in emails through tracking, templates, AI-optimization, and proofing. Test different approaches, personalize at scale, leverage data, and put your best writing forward. With these tools, your wit will lead to more wins.

Here are key takeaways for the overall article on writing funny cold emails:

Summary for Writing Hilarious Cold Emails

  • Humor helps you grab attention, build rapport, boost engagement, and be remembered. But tailor it to your brand voice and audience.
  • Do your research to understand your prospects’ demographics, cultural background, interests, and sense of humor. Personalized comedy lands best.
  • Opening with a funny anecdote, telling an engaging story, using industry puns, and more can make your email shine. Balance humor with concise professionalism.
  • For subject lines, leverage pop culture references, exaggeration, funny questions, wordplay, and observations about their business.
  • In follow-ups, reference previous jokes, compliment positive replies, and demonstrate listening with personal details. Avoid overusing humor across sequences.
  • Ensure humor aligns with your brand voice and steer clear of controversy. Don’t let jokes seem unprofessional or overshadow messaging.
  • Leverage tools like email tracking, templates, AI writing, and grammar checking to optimize and scale humor. Let data guide your efforts.
  • With practice, you can become a humor pro. Comedy in cold outreach boosts responses when done strategically. Bring a smile to your prospects’ faces while also driving revenue! Here are some frequently asked questions about using humor in cold emails:

Frequently Asked Questions

Why should I use humor in cold emails?

Humor makes your outreach stand out, appear more human, build rapport, boost engagement metrics, and make you memorable. Laughter triggers positive emotions that make people more receptive.

What types of humor work best?

Personalized jokes based on research of their interests, subtle wordplay, observational humor about shared experiences, and brief anecdotes tend to perform well. Self-deprecating and exaggerated humor can also be effective.

How much humor should I use?

Aim for humor in the subject, opening, and maybe one other spot. Too much comedy can seem unprofessional or make the pitch get lost. Keep most of the email focused on concise benefits.

Should I use emojis, memes, gifs?

Use them in moderation if they fit your brand voice and audience demographic. Test performance with/without them. Overuse can seem unprofessional. Follow prospect reactions.

What topics should I avoid for humor?

Steer clear of controversial subjects like politics, religion, race, and gender. Email lacks the context of in-person comedy. Avoid anything that could alienate prospects. Save riskier humor for when you have an established relationship.

How do I know if my humor will work?

Research your target audience and test different humor approaches in A/B testing campaigns. Track open, click-through, and reply rates to see what resonates. Refine over time.

How can I optimize and scale my humorous emails?

Use templates with merge fields to add personalized humor efficiently. Leverage AI tools like Phrasee to data-drive subject lines. Use humor analytics to double down on what converts.

How can I avoid mistakes or typos?

Use an email tracker to test messages before sending. Have a colleague review emails and humor. Use a grammar checking tool like Grammarly to catch errors. Proofread carefully!