I’ve long held the view that in all things art and design, you can feel the spirit and demeanor of those who create them. That’s why it was no surprise to me that David Karp is one of the nicest, most empathetic people I’ve ever met. He’s also one of the most perceptive, capable entrepreneurs I’ve worked with.

—Marissa Mayer, the C.E.O. of Yahoo!, on her company’s deal with Tumblr

Dear David,

It seems like only yesterday I asked a Yahoo! intern to explain to me what a “Tumblr” was, but when I saw that dashboard, full of content being created and shared by demographics that weren’t even born when my company started, I knew that I wanted—no, needed—to acquire you. The results from my Yahoo! Internet search only confirmed what I knew in my heart: David Karp is one of the nicest, most empathetic people on the planet, and we would make great partners.

Affectionately,

Marissa

* * *

Marissa,

Am I just another start-up to add to your collection? Did you whisper the same sweet nothings to Summly, to Astrid, to Loki? I saw what Yahoo! did to Flickr—cast aside and forgotten for years, like so many “e”s—and I don’t want to be hurt in the same way.

Fuck no,

David

* * *

Oh David, you wound me! I’m not like those other Yahoo! C.E.O.s. I am drawn to your wit and your irreverence and your youthful user base like a moth to a flame. San Francisco seems so much gloomier now that I’ve glimpsed your vibrant East Coast start-up world. I could charter a private jet to visit you this instant, but even though I can fly across the country as easily as I cross the street, I fear I’ll never be able to bridge the chasm that lies between our hearts.

Marissa

* * *

Lovely Marissa, I fear I have nothing to offer you. I have no real monetization strategy, no revenue to boast of. I know you’re a strong, powerful woman in the tech industry, but I can’t help how I feel as a man: sometimes I just lay in bed at night, worrying about how I can provide for you. And what will my users say when they see me with the Internet’s oldest media network? Sometimes I wonder, with all these question marks, if the declarative punctuation our logos share is really enough to sustain this relationship.

Regretfully,

David

* * *

My darling David,

Don’t let these earthly considerations stand in the way of our relationship. Getting to know Tumblr has been the biggest joy of my life. I have never felt so young, so alive, so full of hope for the future as when I am watching your metrics rise exponentially each day.

Oh, I was looking at some of your photos online the other day. Please don’t wear your Google Glass when I introduce you to my board. I want them to approve of you.

All my love, Marissa

* * *

My beloved M.,

I cannot simply change who I am or what I do to win the approval of those around you! I would be letting down my community and myself—and, I think, I would be letting you down, too. We both know what’s really behind this, and I’m sorry if my wearing Glass brought up some unhappy memories for you. I just need you to be honest.

David

* * *

My dearest,

I’m sorry if you felt attacked—I know I promised not to screw this up, and to let Tumblr be Tumblr, but with so many people watching us, the pressure becomes too much sometimes.

But my board liked you—really, really, really liked you! They think we could build a really beautiful audience together. Yes, they worry about monetization like any good board does, but I told them that you were working hard on a plan and that you would be so successful next year if they just gave you a chance. And a billion dollars.

Lovingly,

Marissa

* * *

David,

You left your iPad here in San Francisco after your last visit. I accidentally turned it on and it just loaded up Tumblr and, well…we need to talk about your porn problem.

Please call me when you have a chance.

Marissa

Illustration by Richard McGuire.