the cut on tuesdays

When You Hit Send Even Though You Know You Shouldn’t

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The Cut on Tuesdays

A weekly podcast from the Cut and Gimlet Media, with host Molly Fischer.

Old emails are a fossil record of our lives. The constant everyday boring things, the big dramatic once-in-a-lifetime things — they’re all in there, trapped like ammonites in the sediment of your inbox. The thing is, it’s so easy to hit send, and once you do, the results are preserved forever.

Now it’s the end of the year, the end of the decade, the end of this show — the perfect time to do some digging.

MOLLY: In general, how do you feel about like looking back through old emails?

ALLISON: Oh my God, I hate it, because I’m a really, um, impulsive emailer.

This is Allison Davis, a writer at the Cut.

ALLISON: The old, common therapist’s advice — which is “sit down, write the email that you want to send, and then don’t hit send” — I only do half of that. I sit down and I write the feelings email … and then no matter what I’ll send it. If I look back at my long Gmail sent inbox or whatever, I do see some growth … before I would send these emails that were just deranged.

MOLLY: In what way?

ALLISON: Well, clearly I was too emotional, and there are misspellings and no punctuation and it looks like a serial killer wrote the email about feelings, and then just — click! You know, sentence fragments everywhere. Molly, you, having once edited me, know that …

MOLLY: I do remember that!

ALLISON: Imagine being my ex-boyfriend and getting that in an email form at, like, 3:30 in the morning.

At least if you send an insane letter by mail, you never have to look at it again. Whatever you wrote, it’s gone. This is unfortunately not the case for email. The evidence of who you’ve been and what you’ve done sticks around in your sent mail folder.

This week, we’re asking our guests to give us a look at some of the messages they’ve sent … and the moments in their lives that they capture. Not all of them are Allison Davis–style feelings emails, but they’re all revealing.

Click above to hear from Allison, Maddie Aggeler, Mona Chalabi, Lisa Miller, Andrea Long Chu, and Stella Bugbee.

When You Hit Send Even Though You Know You Shouldn’t