Freelance Marketing: 5 Meet-Cute Ways to Get Hot Clients


Looking for a freelance marketing script to turn prospects into clients?

Go watch some rom-com.

For example, at the conclusion of When Harry Met Sally, there’s this memorable scene:

    • Harry declares his love for Sally.
    • They kiss.
    • Cue Auld Lang Syne and slow dancing.
  • Fade to black, and everyone is happy.

Wouldn’t it be nice if your freelance marketing efforts worked the same way?

Just send a pitch. Fire off a query letter. Write an LOI (letter of introduction). And your proposed client will fall in love.

Fade to black, and you have oodles of work.

Well, things rarely work like they do in the movies. Or maybe they do…

“Harry” and “Sally” go through a series of meet-cutes, or phases in their relationship before they get together.

And that’s something you should pay close attention to if you want to be a successful freelance writer.

When you understand how client relationships develop (like the formula for a rom-com), your freelance marketing efforts can help you get noticed, move up, and earn more.

Want to know how to get hot clients to pay attention? Here’s what you need to know about the freelance marketing meet-cute.

Meet freelance writer Larry Bernstein

Freelance Marketing: Bernstein

Larry Bernstein

Larry Bernstein is a New York-based freelance writer. He specializes in writing in the construction, education, and retail niche.

But his freelance career wasn’t a straight line to success. He worked in marketing for architectural and engineering firms. And he taught high school English for 10-plus years before making the leap to full-time freelancing.

“My marketing primarily happens by way of LOI’s,” says Larry. “While some exchanges do indeed lead to work quickly, most responses are like an opening salvo. The potential for a relationship has arisen. The goal is to make that relationship come to fruition.”

So what can you learn about freelance marketing from rom-coms?

1. It takes time to turn prospects into clients

Ever seen a rom-com where the main characters fall in love in the first five minutes?

Nope. It doesn’t work that way. And neither does freelance marketing to get clients.

  • Be patient. The length of time between an exchange with a potential client and actual work can vary greatly. For marketing to be successful, it does not necessarily have to lead to instant work.
  • Play the long-game. This is especially important to keep in mind during times of uncertainty. That’s why it’s important to follow the advice of the Freelance Writers Den mother Carol Tice, and build an emergency fund.

This relationship perspective and emergency fund can ease the pressure that we may feel about freelance marketing at this time.

2. The meet-cute process of freelance marketing is rarely love at first sight

Almost every rom-com begins with some kind of blunder, unexpected turn of events, or even random encounters. And there’s usually some awkward, uncomfortable, and funny moments, or maybe nothing happens…at first.

Guess what? Freelance marketing is sometimes like that, too.

  • Some freelancers—myself included—may feel somewhat uncomfortable marketing during the shutdowns, pandemic, and recession.
  • After all, do companies need to hire a freelancer when they may be facing cutbacks, layoffs and furloughs?

Here’s the thing. Plenty of companies absolutely are in need of freelancers even during this tumultuous time. As noted in The Recession-Proof Freelancer, “There are always clients out there, if you’re willing to hunt for them.”

Reach out, make connections

It’s your job to reach out (that’s freelance marketing) and let potential clients know how you can help them. It’s kind of like the goofy girl or lonely guy in a rom-com trying to muster up enough courage to say “hi,” and get noticed.

  • If they need someone or recognize a need by your inquiry, it’s good for them and good for you.
  • Or, they may not need someone right away. Times can change though as the country starts to open up.

It’s not about pouncing during a dark time but instead developing a relationship that can ultimately be mutually beneficial.

3. Zero expectations is a good way to start relationships with prospects

The initial pitch letter, query, or LOI can easily sound like an all-or-nothing proposition.

  • Here’s my idea.
  • Check out my credentials.
  • Do you want to work with me.
  • Yes or no? Chop, chop.

But you know how well that works out for the overly-confident, self-absorbed character in a rom-com, right?

It’s called rejection. And that’s not the result you want from your freelance marketing efforts.

With a couple of simple additions, your pitch, query, or LOI can act as a starting point for a relationship and not an ultimatum.

Here’s a line I use in my LOI script:

If you and (company name) are looking to beef up your content now or in the future, I’d love to hop on a call, learn more about the company, and spitball some ideas with you. 

So far, multiple companies have asked me to get back to them when things settle down while others have taken me up on my offer to share ideas.

Want to make a good first impression? Use these phrases in your freelance marketing LOIs:

  • ‘Now or in the future.’ By noting ‘now or in the future,’ there is a clear recognition that the need for a freelancer may arise at a later date. This shows you’re in it for the long haul and appreciate that the need for a freelancer may occur in the future.
  • ‘Learn more about the company.’ This shows the desire to understand the company and appreciate their history, approach, and challenges. Such information is critical to producing useful content and demonstrates an interest in the company.
  • ‘Offer valuable ideas.’ Carol Tice says, ‘We’re paid to think.’ By offering ‘to spitball some ideas,’ and ultimately offering valuable ideas, you’re proving that you can think and add value.

When you follow the rom-com formula for freelance marketing, make a good first impression, and keep it simple. Chances are good your prospect will notice, and ask you out for “coffee.”

4. Little reminders build trust with prospects

Developing a relationship means going beyond the initial contact.

You know, in a rom-com, there’s always a bunch of stuff that follows that first encounter. Emails, text messages, phone calls, a letter in the mail, the convenient run-in at the coffee shop.

How can you do this to develop relationships with prospects? There a number of ways to do so related to freelance marketing:

  • Use social media. Determine which social media outlet(s) the company is active on and follow them there. And then, be social – share, like, retweet, comment.
  • Use LinkedIn. Connect with prospects on LinkedIn. Leave thoughtful comments, and share their posts.
  • Study the prospect’s website. Periodically check out the company website for new blog posts, news releases, announcements, product launches, etc. Send an email to say “hi,” and mention something specific about their online presence.
  • Share useful content. If you come across something that may interest your prospect related, share it, email it, send a DM.

None of this guarantees work, but it ABSOLUTELY is the way to build a relationship and keeps you top of mind when the illusive moment of need for a freelancer arises.

5. Long-term client relationships are good for freelance-writing success

Building a relationship is time consuming. So, you want to limit the number of perspective employers/relationships you’re working on.

Make sure the company you plan to pitch is worth the investment of your limited time.

  • Study your prospect’s site, blog, product/service pages, and social media channels.
  • Find out how many employees work there.
  • Look up their annual revenue data.
  • Check to see if they work with other freelancers.
  • Look for prospects with investor funding or established companies on the rise.
  • If it looks like a dead end, don’t ask the prospect out on a date.

Believe me, this will save you a lot of heartache later. Working for low-paying, soul-sucking clients is not going to lead you to a rom-com-inspired happy ending.

By the way, it took approximately 11 years from when Harry met Sally until they got to the climactic New Year’s Eve scene.

Use the Meet-Cute Formula to get freelance clients

Feeling a little desperate to get more freelance clients? When an initial contact doesn’t lead to immediate work, don’t get discouraged.

Keep marketing. Develop relationships with the prospective clients you really want. That way you can also fire bad clients you don’t want to keep working with.

And ultimately, you’ll find some clients with whom you’ll be dancing at midnight on New Year’s Eve.

Need help with freelance marketing to get clients? Let’s discuss in the comments below.

Larry Bernstein is a New York City-based freelance writer He also likes sports, Bruce Springsteen, and his wife and children (most of the time).

Recession-Proof-Freelance Writing - MAKEALIVINGWRITING.COm


  1. Kaitlin Morrison

    Hey Larry,

    Loved the rom-com spin on these freelancing best practices! Maybe I should take a break and watch one sometime soon to look for marketing inspiration.

    I think I’ll have to try “now or in the future” language. I keep my LOIs so short and direct that I worry sometimes that prospects will drop my note in the trash if they can’t immediately go to coffee.

    Thanks for the article! Fascinating take. When a prospect isn’t very interested, I’ll have to remind myself I must just be in the first ten minutes of a rom-com, and not quite at the end just yet.


    • Larry Bernstein

      Thanks Kaitlin. I’m no expert on RomComs but “When Harry Met Sally’ is a classic so if you are looking for one to watch…
      Good luck with the new language. Hope it proves helpful with your marketing/LOIs.

      • Holly Bowne

        And ditto what Larry said. “When Harry Met Sally” is a classic!

  2. Precious Marho

    I absolutely loved this, Larry!

    Very informative and practical.

    Thanks for sharing.

    • Larry Bernstein

      Hope it helps you grow your list of clients, Precious.

  3. Holly Bowne

    Great advice presented in a fun way! Thanks, Larry! (I had no idea you were a rom-com fan. Ha, ha!)

    • Larry Bernstein

      It’s all my wife! Ha ha.
      ‘When Harry Met Sally’ really is a very good movie.

      Glad you appreciated the advice.

  4. Regina Zielinski

    Love these tips! I just saw “The Holiday” where meet-cute was used. Genius way of using an old Hollywood concept for a creative slant.

    • Larry Bernstein

      Thanks Regina.
      I don’t know the movie, but I’m not surprised to hear about the formula.

  5. Alexis Taylor

    Great post Larry! I loved the bit about lines to include your LOI that leave things open ended. Thank you for sharing!

    • Larry Bernstein

      Sure Alexis.
      Hope if you decide to use these lines that they prove beneficial for you.

  6. Beth Casey

    Great article and tips! Thanks!

    • Larry Bernstein

      You got it, Beth.
      Hope the tips help your business grow.

  7. Wariebi

    This is a great and helpful tip!

  8. David Hicks

    Great concepts. It reminds me of my experiences on go through a lot of candidate “dates,” pick the ones you think will be the best fit, and start making polite inquiries! 🙂


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