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It’s About the Destination, Not The Journey

My tell-all from the passenger seat of one loooong ride


In partnership with Cadillac.

I will be the first to admit that Amelia and I have a unique working relationship. We’re friends who became co-editors who have gone on to complete sentences for each other that we did not even know we endeavored to say. It’s ideal in many ways, strange in others but fundamentally and most importantly, it’s pretty damn fun. So when the possibility of taking a road trip came up with Cadillac, one of our Fashion Week sponsors, it seemed like a good idea.

Great, even.

We could tell jokes that would snowball into story ideas! Use the highway as a metaphor for life in a collection of thoughts that could be optimized for Snapchat! Treat the car (an Escalade) as if it’s a studio apartment and therefore a place to store our dreams. We could then share those dreams and most importantly, we could hit the breaks at every fork between Manhattan and Montauk to stop, drop and Instagram.

A week following the road trip, I have just this to say: no matter how much you love Larry David, he is not the person with whom you want to spend three days in a car. And seeing as Amelia’s Repressed Larry David Syndrome has become a case of Full-Blown Psycho David syndrome, I must admit there were at least two moments where I honestly feared for my life. The first time was when we were leaving Manhattan. She kept saying Manhattanites are like city-dwelling pigeons, because just like these pigeons don’t see humans as predators, the Manhattanites don’t see moving cars as a threat. One might argue they hope to get hit: “Come at me, luxury car,” she muttered, doing her best pedestrian impersonation. “I could use the cash settlement.”

I think she was getting at murder.

Once out of the tunnel and city, the first stretch of our drive (some 150 miles) went as smoothly as a glass of expensive wine down the throat. We shared raw chocolate goji berry things, listened to music and talked about life. Then we hit traffic. And in a very brief moment, the devil came out. I invite you to step into the following, undramatized monologue.

“If that f***ing car in front of us was a f***ing gazelle, a lion would eat it so fast.

I’ve seen that f***ing car on National Geographic.

It gets eaten by the lion. F***ING MOVE! WHAT ARE YOU DOING! I’m going to crash into it.

On purpose.

That f***ing car.”

Mind you there is traffic. There is no where for this little sedan in front of us to go.

Additional things I learned about Amelia: she does not understand the concept of pacing but does nurture those she is driving. (Example: she stops short every time a car ahead of her begins to slow down and flings her arm out towards the passenger seat, where I am, to make sure that in the event my seat belt is faulty, her limber arm will come to my rescue). And in spite of how profoundly awful she is at backing out of a parking lot, there are plenty more good qualities and intentions where her limber, flexing arm came from. I just can’t remember them.

Verdict? If life is a highway, your co-pilot doesn’t have to be sane. Reflexes, snacks and an army of sing-alongs, however, are a must.

Update: Hi. Amelia here. You know what I have to say to all that? She who holds the aux chord and the wheel has the last laugh. So HA.

In partnership with Cadillac.


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  • Stephanie

    Your parking lot outtake reminded me why I am afraid of driving large cars! Give me a small car any day- so much more forgiveness when it comes to parking!

    • Anna.M



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  • Allie Fasanella

    my friends and i call the arm move ‘the blind side’ like the movie with sandy bullock because that’s what big mike does for the little kid and it saves him. i too, tend to do this.

    • Amelia Diamond


      • Amelia Diamond

        also, Leandra, why didn’t I ask you this? did you feel like the guy in the TLC song No Scrubs?

        “Hanging out the passenger side
        Of his best friend’s ride
        Trying to holler at me”

  • Martine

    Did you drive a thousand miles?

    • Amelia Diamond

      If I could
      Just see you

  • Liz Warners

    My coworker became my roommate! That’s like a road trip of life, right? I must say that Cadillac is much nicer than our apartment though.

    • My roommate is my coworker too!

  • Alba B.

    Hi Leandra,

    Road trips to me = falling asleep
    How were you able of not falling asleep during the road trip? Please could you tell me the secret 🙂 …Thanks in advance

  • Aydan

    I’m a life time passenger. I’ll bring the snacks and tunes so long as someone else drives!!

    • Lua Jane

      Same here. Nonedriver and a lifetime passenger. I try to be a good sport though whenever the person holding the wheel get’s onto the regular psychotic driver antics. I came to believe it comes with the process of driving.

  • I’m sure a road trip with MR co-workers would make for one helluva blog post.

    Josh | The Kentucky Gent

    • Leandra Medine

      DIDN’T IT?

      • Totally did. I was just hinting at wanting an invite next time around.

  • I honestly thought that Leandra might have walked up to the farm stand wearing nothing but a bandana around her neck…

  • forget t-swift, this is real squad goals.

  • Mae

    Consider this notice that the “guys on bikes” lyric replacement is being stolen and used at all times because it’s the best thing I’ve ever heard.

  • Lua Jane

    How on earth do you teo manage to be so lovable at all times?!

  • In sum, this, inclusive of bandanas and FUPAlicious jeans but minus the ending


  • long

    Crazy Craft

    Your parking lot outtake reminded me why I am afraid of driving large cars! Give me a small car any day- so much more forgiveness when it comes to parking!

  • you guuuuuuys

  • loulee

    My 2 year-old son saw that picture of you at the produce stand on instagram. He asked who you were and then kept saying “Wan go swimmin wit Wandwa”.

  • Greer

    THAT CAR IS HUGE! Or are you just tiny? No that car is definitely huge. I know you’re not tiny. That car is literally gigantic. So freaking huge.

    • Greer

      Next time I’d also like the vlog to have danker editz

      • Amelia Diamond

        like really cool spiraling tranzitionz?

        • Greer

          yeh and maybes even some word art 2003 titlez

  • Hahaha, great road trip!


  • Andrew B

    Making use of the scrap paper at my library because it deserves adorable brandishing over mere shredding. The way you accessorize with a vehicle gives me accou-tremors!

  • cheyfoster

    I once responded to a church list serve post to drive a 1998 Saturn coup from DC to Salt Lake and took my coworker-turned-friend on the journey. Ten days and a few wildly irrational arguments later, I discovered a few important things: lyrics to Shania Twain songs never really leave your brain, my body still maintains a two-drink maximum, and Nebraska really is the worst.

  • Vanessa

    Amelia you have amazing hair!

    • Leandra Medine

      do not perpetuate her vanity, vanessa! it is a slippery slope.

  • Ignatius Reilly

    Repellent? Your clothing is a ruse, getting me to undress you with my eyes.

    I’m on to you, girl.

  • Amelia just summarized my entire life of taking photos with “oh my god, my chin.”

  • Claire

    this is beautiful. I want to go on a road trip now…. with a driver I trust. 😉

  • Katherine Sargeant

    Just left the Hamptons on Saturday from the most amazing summer, getting a weird nostalgia about Montauk Highway traffic

  • Clark Hastings

    I may have to side with Amelia on this one. Drive for more than 1 day in Los Angeles & I’m sure you will agree. That little sedan in front of you SHOULD have sprouted wings and flown. Obviously.

  • Tanya Brennand-Roper

    Hey Leandra! Where are your amazing sunnies from? xx