We’re deep in the sweaty recesses of campaign season, which means our inboxes are constantly crammed with desperate pleas from disappointing people. Coincidentally, the same thing tends to happen right about now with our former flames, who tend to use this meditative time of year to reflect on how shitty they are.

The result is a bit of email confusion: at a quick glance, it’s surprisingly difficult to tell whether that pleading missive is from the Democratic National Committee or someone who’s been repeatedly instructed to lose your number.

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To demonstrate, we’ve been collecting both fundraising emails, and, at risk of subjecting the entire office to a bit of light PTSD, very real emails from Gawker Media’s exes. And now you get to guess which is which!

1.

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Tricky one! Is it “important” that we donate $5 today, or important that we understand that was not what that looked like, she’s just a work friend? Find out below.

It’s the Democratic Congressional Campaign Committee, pretending to be your commander in chief!

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2.

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Put a record donation on the books? Put a conciliatory drinks evening in your appointment book? Or perhaps book a time to fuck off instead?

Oh, yep, it’s someone’s ex.

3.

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Who needs you that much? You can probably guess.

That there is Congressman Dr. Raul Ruiz. He’s currently running for reelection in California, and his fundraising emails were (fun fact!) so relentlessly thirsty they generated this entire post idea. He needs you, and us all.

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4.

An email marked urgent from someone expressing all-caps concern? It can only be...

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That’s Annette Taddeo, a candidate for Congress in Florida. We can’t recall just what she’s concerned about but it does seem pressing.

5.

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Do you?

Nope, you don’t, because that is someone’s ex, phrasing things in maybe the least romantic way possible.

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6.

Let me guess:

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That one had ex all over it.

7.

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Oh, hmm—look towards the spring campaign season? Look towards spring when I will recapture your heart?

Oh yeah. That was an ex.

8.

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Uh oh. Could it be....

As we suspected, that is Senator and person who wants to be president Ted Cruz, letting us know it “must be wrong” that we’re listed as not having donated to his campaign yet. (If donating to you is wrong, Ted... we don’t want to be wrong.)

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9.

I hate the sound of this one.

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As expected, that is Congressman Dr. Raul Ruiz again, who could possibly chill just a touch.

10.

And for our gut-wrenching finale:

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Oh God.

Wow, I really, really wanted that one not to be an ex.

That was upsetting! Before we go, we’ll leave you with a final thought, from a Gawker Media staffer who graciously plumbed his or her inbox on our behalf: “I need a Klonopin.”

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Contact the author at anna.merlan@jezebel.com.

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Lede image and question mark man via Shutterstock; politician graphics by staff male Bobby Finger