I Mail Hand Written Love Letters to Strangers – Part 1
I Mail Hand Written Love Letters to Strangers – Part 1

I have hand written and mailed love letters to complete strangers.

Well, maybe not complete strangers – but pretty close.

Just one of the many ways I’m quite unique. But it’s true.

Three different men, three different poems, three different times in my life.

And it was awesome.

But why am I sharing this embarrassing info with you? Why am I choosing to show my cards, to broadcast to the world that I clearly don’t care what may be the socially acceptable norm? 

Well, because I want to inspire you to live a little. To loosen up. Stop taking life too seriously and have a little fun. 

Because it doesn’t have to be that serious.

These stories have been the topic of much uncontrollable laughter, sore cheeks, and full hearts for me and many of my friends.

So go ahead and laugh with me. You can call me silly, ridiculous, or crazy. But I’m not sorry that I like to keep life interesting. Keep things fresh. Keep people on their toes.

Also, let’s be honest. This ish is hilarious.

You’re probably wondering how the hell this all started, right? Let’s start at the beginning.

Mystery man number one. 

The first time I ever decided to put pen to paper, stamp that envelope, and mail my feelings to an unsuspecting stranger.

So, let’s dive right in!

Side note: Don’t judge my behavior. You’ve all been there.

*Also, I swear this would only happen to me.

Eligible Bachelor #1: The Boy In The Beanie

One night while I was drunk and hopping around the beach bars in Jacksonville Beach, I met this boy.

He was really cute and we hit it off instantly. We had some really great conversations and I got really good vibes from him. So hell, I decided to go home with him.

He was honestly so sweet. We talked for a long time. He said incredibly nice things to me. And we kissed. A lot.

As time went by I finally realized it was super late, and I had to catch a flight in the morning (at this point I was a flight attendant based in Chicago, so I had to leave Jacksonville to head up north for work).

He was taken back by how abruptly I had to leave.

I quickly passed him my phone so he could tell the Uber where it would be picking me up – because clearly I didn’t know his address.

We spent the next few minutes talking before I fled like Cinderella to catch my Uber.

The next morning I woke up feeling like hell. One of those mean hangovers that follows a night of remembering close to nothing. A shining moment for me.

As I thought back on the night before, so much was cloudy.

I remember being with a boy I really liked, but I couldn’t remember where or how I met him.

I remembered some of our good conversations and the sweet things he said to me, but that was about it.

But then something terrible hit me: I realized we had completely forgotten to exchange numbers.


You know what’s even worse? I didn’t even remember his name.


Thanks, Whiskey. You da best.

I sat there in disbelief. I must have gotten his number at some point, right?

I went through all the contacts in my phone hoping to scroll past a name that would jog my memory. Nothing.

I then searched my social media accounts for any recent additions to my friends list. What?! Nothing there either?

I didn’t remember what area he lived in. I didn’t remember what bar I had met him at. Nothing.

How could I be so incompetent? I didn’t remember his name or have a way to contact him?! What the heck is wrong with me? I had one job!

Side note: To be fair, I’ve had many friends point out my shit memory after only a few drinks. It’s a curse.


As I thought and thought about how I could get in contact with him again, I finally had an idea.

I used Uber last night! Uber picked me up at his place! The last pickup address in my account is where he lives! BINGO. I’ve got him! I at least have his address.

This time I’m going old school on him. No text. No DM. A fucking piece of mail. I’m mailing this kid a letter. A LOVE LETTER. YES.

How could he resist a love letter? No one does this anymore. You’ve got to appreciate the initiative and creativeness behind it.

Plus, I was pretty sure he was into me. So I wasn’t risking much.

But then I realized, “Christine you idiot, you don’t even remember this kids name. Who are you addressing this letter too?”

I did remember what he looked like though. 

Something you remember…about time Christine.

He was a cute brunette wearing a beanie. That’s it!

From then on out, Bachelor #1 was referred to as Boy in the Beanie.

Adrenaline raced through me at the thought of mailing this kid a love letter. Well, a poem actually.

This was so exciting. I sat down immediately to write it.

It turned out wonderful. 

This is what I came up with:

I stumbled across you Sunday night
Down near the beach bars
Don’t really remember when or how
But I remember who you are

You scooped my back to your place
Where we really vibed
But then I had to flee the scene
My plane home was soon to fly

We were too caught up in each other
And forgot to exchange phone numbers
The Jack Daniels had me feeling stupid
But you made me feel like I was shot by Cupid

I hope you enjoyed this little ditty
I wanted to reach out from across our cities
For work I fly from place to place
But I will be back, Jax is my home base.
Plus, I’d like to see your face.

Call me, Christine *with my number

Yea, I was pretty proud.

I addressed it to Boy in The Beanie, wrote down his address, kissed the letter for good luck, and placed it in the mail. I couldn’t wait to find him!

A few days went by as I patiently waited for a response.

One Sunday morning in Chicago I was out for brunch with some of my closest friends (who I had told about the letter).

As we’re sipping mimosas and chomping on some bacon, I get a text from a random number.

The first thing I see is a photo of the envelope I had sent – Oh my god! He got the letter!

I proudly interrupted my friends to read aloud the text I received:

“I got your letter to the boy in the beanie. I’m sad to say you’ve got the wrong address.”


I was heartbroken.

I was sad, a bit tipsy, and scared that this might actually be some hidden girlfriend just shooeing me away.

He didn’t have a girlfriend did he?! How is this the wrong address?

She insisted to me that she was not indeed the girlfriend.

After a sigh of relief, the next chapter in this saga began after her next text:

“This letter is hilarious and I want to help you find him. There’s an apartment complex behind my house, maybe he lives there. Tell me everything you know about him. I’ll put up flyers looking for him. I want this love story to come true!”

At this point I was so damn happy I was a bit tipsy with friends who knew the story. This was getting too funny!

We all died of laughter and excitement.

From here on out I called this girl Tink, like Tinkerbell. 

After all, she was like my fairy godmother now searching for my prince.

I decided to send Tink all the info I knew that could maybe help us find him; what he looked like, what I looked like, and random bits I remembered from the day we met.

Basically, anything she could put on a flyer to try to track him down.

I couldn’t believe this was now going so far that a complete stranger was making and posting flyers around her neighborhood searching for my missing Boy in the Beanie.

Does this really happen?!

She even made a special email account for him to send his picture to so we could verify him first – straight ‘Cinderella and the glass slipper’ style.

This way we could also weed out any creepers that weren’t really him. 

She then sent me a picture of the beautiful and hilarious flyers, and I knew I could trust her.

I was so excited to now have Tink on my side.

We were going to find him!

A few days turned into a few weeks, and Tink had no leads.

No one had reached out, and no one had emailed us.

I was really sad. I had tried everything I knew how to find this guy. 

And it was over.

A few weeks later I flew back home to Jacksonville to spend the weekend. I spent Friday night with friends at my favorite bar at the beaches, Lynches.

Two drinks into the night, I head over to the bar to grab another whiskey and coke.

I turn my head at the bar to check out who I just weaseled my way next to, and I locked eyes with this gorgeous, tall brunette guy.

He looked at me, and I looked at him. And we both knew.

“It’s you!” I shouted uncontrollably at him. He recognized me immediately.

He gave me a big hug and before he could pull away, I had my phone placed promptly in his face.

Pleaase give me your number before we lose each other again.

He laughed, having zero idea of the effort I’d gone through to just unsuspectingly meet him in the exact place I clearly had met him last time, and put his name and number in my phone.

Zach. His name was Zach. Finally, an actual name.

But in very Christine fashion, I changed his name in my phone to Boy In the Beanie. Because after all I’d been through, this was his real name now.

We chatted for a while. He told me this is where we met last time. Of course.

The universe is funny that way.

Not really worried if I would scare him off or not, I told him this entire story. Showed him the texts with Tink. Read him the poem.

He absolutely died of laughter. He loved it.

And you know what? We’re still friends to this day.

(Hi, Zach if you’re reading this!) 

*please god don’t be reading this*

So, that's it.

I decided to do everything in my power to find this guy and the universe (along with another stranger) conspired to help me.

If this hilarious anecdote doesn’t inspire you to live a little, then I don’t know what will.

Though this is probably the best of the three stories of me mailing my emotions to strange men, I do have two more.

And lucky for you, they all share the same theme:

Don’t be afraid to put yourself out there for a laugh. You never know what could happen

See you back for Part 2!

Leave a Reply

Close Menu