September’s Pen Pal Theme- Something I’m Afraid to Tell You.

Hello Strangers,

September’s WLA theme is here, and this month, we’re getting a little more honest.

Something I’m Afraid to Tell You.

We all have things we’re afraid of. Some are big, some are small, some make perfect sense, and some are difficult to explain.

Maybe you’re afraid of failing at something you really care about. Maybe you’re scared of getting older, disappointing someone you love, never finding your place, losing someone, being misunderstood, or making the wrong choices.

Or maybe there’s something you’ve been carrying for a long time that you’ve simply never had the chance to put into words.

For this round, you’ll be writing to your pen pal about a fear you don’t usually talk about.

Tell them what you’re afraid of, where you think that fear comes from, how it affects you, or what you wish you could tell someone about it.

You don’t have to share your deepest secret or anything that makes you genuinely uncomfortable. Vulnerability has no fixed definition, and you get to decide what you’re ready to share.

Your letter can be serious, funny, messy, thoughtful, or a mixture of all four. There’s no right way to do it.

Then your pen pal will do the same.

The goal is simply to create a space where two strangers can be honest about the things that scare them and discover that they may not be as alone in those feelings as they thought.

How It Works

Step One: Write Your First Letter

Write a letter to your pen pal about something you’re afraid to tell people.

You might include:

• a fear you’ve carried for a long time

• something about the future that scares you

• an insecurity you rarely talk about

• something you’re afraid of losing

• a decision you’re scared of making

• something you worry people might misunderstand about you

• a fear you’re currently trying to overcome

You don’t have to answer all of these. They’re simply there to help you get started.

📅 Deadline for first letters: August 31st

Step Two: We Match You

Once submissions close, we’ll pair everyone with a pen pal and send your letters out by:

📅 September 2nd

Then comes the best part.

Step Three: Read & Reply

After receiving your pen pal’s letter, write back and share what resonated with you.

Maybe you’ve experienced the same fear. Maybe you see it completely differently. Maybe their letter made you think about something you’ve never considered before.

You can tell them what you related to, what surprised you, or simply let them know that you understand.

To participate, you must be a paid subscriber to With Love Anonymous.

📅 Deadline for reply letters: September 14th

That’s it.

You don’t have to have conquered your fear before you write about it. You don’t need to have an answer or a solution.

Sometimes it’s enough to say, “This is something I’m afraid of,” and have another person listen.

We’re looking forward to reading your letters.

With love,

Anonymous