May Lettering Prompts (Challenge + Free Worksheets)

Is it just us, or is it feeling warm in here?! The month of May is one of the most anticipated months of the year, and these May hand lettering prompts will help you take stock of the change all around you.

Finally rising temperatures, fresh flowers, Cinco de Mayo, Memorial Day, sitting in the grass - the list of little joys goes on and on.

Instead of abandoning your compositions for picnics and gardening (don't break our hearts!), let this month's prompts inspire you to bring some of that creativity and spirit into your lettering practice.

Pin it for later! ↓

 
Pinterest image
 

The best way to improve your hand lettering skills is to have fun, get out of your comfort zone and practice more often.

These May lettering prompts will help you do just that!

We couldn't be any happier that you're here. We're Jordan (left) and Jillian (right), the twin sisters behind Loveleigh Loops.

 
Jillian and Jordan doing hand lettering

We’ve taught more than 140,000+ calligraphy students online, and we’d absolutely love for you to join us!

 

These lettering prompts are part of our seasonal blog series aimed at bringing variety back into your calligraphy and hand lettering practice.

...and just the tip of the blog iceberg. Besides this free blog series, we have enough lettering posts to keep you busy for the rest of the year!

We know that no matter how much you love hand lettering, doing the same thing over and over again gets stale. That where these May hand lettering prompts come in to save the day.

In this month's practice prompts, you'll get:

  • Daily prompts for the month of May

  • Free practice sheets

  • Style suggestions

  • Community support in our Facebook group

Let's dive in!

Table of Contents

    31 May Hand Lettering Prompts

    The challenge: Write one of these May-themed hand lettering prompts per day. The goal is to make practicing fun and easy, with no decision-making necessary on your end.

    There are no rules, except to stay excited about your progress.

    You can use any supplies that you have on hand, from calligraphy pens to basic markers. If you're a beginner, we'll share free practice sheets in a minute that you can use to help you learn.

    1. Hello, May

    2. Crisp and clean

    3. Peonies

    4. May the fourth be with you (in honor of Star Wars Day, May 4th)

    5. Cinco de Mayo (May 5th)

    6. Sprout

    7. May harvest

    8. Breathe deep

    9. Daffodils

    10. Luscious

    11. Blooming flowers

    12. Happy Mother's Day (May 12th, 2024)

    13. Here comes the sun

    14. Fresh rain

    15. Flutter

    16. Robin's egg blue

    17. Break out the bikes (in honor of Bike-to-Work Day, May 17th)

    18. Lily of the valley

    19. Blossoming blooms

    20. Buzzing bees (in honor of World Bee Day, May 20th)

    21. Family time

    22. Sun-drenched fields

    23. Come alive

    24. Tranquil

    25. Lavender

    26. Windows open

    27. Memorial Day (Memorial Day, May 27th, 2024)

    28. Fresh cut grass

    29. Caterpillar

    30. Almost summer

    31. Whimsy

    Easy tip: Leave your lettering supplies out where you can see them so that you can instantly go from zero to practicing.

    We’re sharing our own interpretation of these prompts on social media… here’s a sneak peek!

     

    Hello, May! Written in Procreate

     

    Tools And Styles

    There are endless writing utensils and styles to choose from when selecting your tools. We share the entire list of our favorite lettering pens in our supply blog post: Favorite Lettering Supplies.

    If you feel like shaking things up from your normal routine, why not commit to practicing with one of these tools and/or styles for the whole month of May?

    Easy practice tip: If you're trying a new tool, make sure to save your work so you can compare your progress from May 1st to May 31st.

     
    Some of our favorite lettering pens

    Some of our favorite pens

     

    Pencil Calligraphy With Flourishes

    Practicing flourishes usually involves a lot of trial and error, and being able to erase is your friend!

    We've taught flourishing extensively, and we always recommend starting with a pencil or on your iPad so that you can tweak, refine and improve your designs efficiently.

    Here’s an example of some practice flourishing with a pencil from one of our Simple to Spectacular students:

     
    Pencil calligraphy flourishing

    An eraser is never more appreciated than when you’re flourishing!

     

    Pointed Pen And Bounce Lettering

    While a pointed pen is a traditional tool usually used to write a traditional script, it's just as versatile as any other writing utensil.

    Bounce lettering is a modern calligraphy style, but it can be written with any tool, even one as traditional as the humble pointed pen.

    If you have multiple nibs on hand, consider trying a more flexible nib. You can see how a more flexible nib leads to thicker strokes and more contrast, creating a more modern look:

     
    A pointed pen writing traditional and modern calligraphy

    Taken from our calligraphy nibs guide

     

    Spencerian Script On The iPad

    The Spencerian script is another traditional style, but it translates beautifully to the iPad (using the Procreate App).

    Here’s an example from Jordan of Spencerian script being written in the Procreate App on her iPad:

     
    Spencerian script written in Procreate

    We have an entire course that teaches iPad Spencerian

     

    While your lettering practice can take any form you'd like, pushing yourself to try new calligraphy and hand lettering skills may introduce you to a style that you love.

    Project Ideas

    Use this time of the year as a great source of inspiration. When we look around, we see nature playing with:

    • Fresh colors: As plants mature, their colors deepen. There's a special lightness to the hues of fresh plants

    • Proportion: Think small leaves on tall trees and tiny animals alongside big ones

    • Emphasis: Growth puts an emphasis on all of the new elements

    These are some of the elements of design that we teach in this blog post: Calligraphy Composition And Design.

     
    Lavender written in calligraphy with a pointed pen

    Lavender written with a pointed pen

     

    Your hand lettering practice can be as simple as writing on a blank sheet of paper, or you can turn your practice sessions into a craft project. Consider creating one of these ideas:

    • Mother's Day card or greeting card

    • Garden sign or potted plant label (perfect for garden Cricut projects)

    • Write a physical letter or note for a friend (maybe with a pressed flower or leaf from your garden in it!)

    Have a friend who'd like to join in the fun? Send them this challenge!

    Free Practice Sheets

    We have 20+ free worksheets in our free worksheet library, and they’re all at your disposal year-round. Here are 3 worksheets that we’re highlighting in May that you can consider trying this month:

    1. Capital Alphabet Worksheet

    2. Copperplate Basic Strokes

    3. “Journey” iPad Quote

     
    Daffodils written in faux calligraphy

    Daffodils written in faux calligraphy

     

    Next Steps

    Let's be lettering friends! We would absolutely love to see you in our Facebook group. You can share follow-up comments, start a conversation with new friends or share your work.

    Come back to the Loveleigh Loops blog for the rest of our monthly prompt posts!

    Favorite blog posts: