Captain Awkward
@captainawkward.bsky.social
Advice blogger, soon-to-be-author. You may remember me as CAwkward on that other site, but I have reclaimed my full title and powers! Here to make new internets to push the bad internets down.
Reposted by Captain Awkward
November 14, 2025 at 9:35 PM
Reposted by Captain Awkward
It’s being reported that Greg Bovino and 250 of his goons will be leaving Chicago. But it’s also being reported that he’ll be back, in larger numbers. But Chicago is a boxer, tired but unbowed. I wrote about how we’ll be ready. dansinker.com/posts/202…
November 14, 2025 at 2:57 PM
It’s being reported that Greg Bovino and 250 of his goons will be leaving Chicago. But it’s also being reported that he’ll be back, in larger numbers. But Chicago is a boxer, tired but unbowed. I wrote about how we’ll be ready. dansinker.com/posts/202…
Reposted by Captain Awkward
We’re fundraising $40k to ensure that the real humans providing that advice can access health care. 99 donors brought us to $6,100 overnight and when we hit $10k, we will receive an anonymous matching gift. Donate here! www.classy.org/campaign/scarl...
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www.classy.org
November 14, 2025 at 5:11 PM
We’re fundraising $40k to ensure that the real humans providing that advice can access health care. 99 donors brought us to $6,100 overnight and when we hit $10k, we will receive an anonymous matching gift. Donate here! www.classy.org/campaign/scarl...
Reposted by Captain Awkward
I listened to the Megyn Kelly clip and my takeaway is that she should change her name to Megyn R Kelly
November 14, 2025 at 3:42 PM
I listened to the Megyn Kelly clip and my takeaway is that she should change her name to Megyn R Kelly
The rejection-sensitive dysphoria-to-praise kink pipeline keeps on piping along
November 13, 2025 at 10:02 PM
The rejection-sensitive dysphoria-to-praise kink pipeline keeps on piping along
Reposted by Captain Awkward
I see the “technically it’s ephebophelia” crowd is out today, so just a reminder that A) this is NOT a case where technically correct is the best kind of correct and B) the minute you say this, the gods dump you in the “irredeemable creeper” basket and wash their hands thoroughly after touching you.
November 13, 2025 at 6:57 PM
I see the “technically it’s ephebophelia” crowd is out today, so just a reminder that A) this is NOT a case where technically correct is the best kind of correct and B) the minute you say this, the gods dump you in the “irredeemable creeper” basket and wash their hands thoroughly after touching you.
Reposted by Captain Awkward
Thank you so much. A huge part of my career has been saying to people who've been through hell, "I see it too. It wasn't you. You're not wrong. This did happen. It WAS that bad." Because if there's one thing toxic systems are spectacularly good at, it's gaslighting.
A true and terrific book that stays with the reader long after. I know you didn't write it as a self-help manual but it did help with healing from toxic people and workplaces, so thank you for that ancillary benefit.
November 13, 2025 at 5:32 PM
Thank you so much. A huge part of my career has been saying to people who've been through hell, "I see it too. It wasn't you. You're not wrong. This did happen. It WAS that bad." Because if there's one thing toxic systems are spectacularly good at, it's gaslighting.
Wholesome: For years my older brother and I swapped identical Borders gift cards for Christmas, wrapping them in increasingly elaborate and incongruous packaging, and saying “I love it!” when the inevitable prize was revealed. This made my mom feral, which only added to our joy.
November 13, 2025 at 4:25 PM
Wholesome: For years my older brother and I swapped identical Borders gift cards for Christmas, wrapping them in increasingly elaborate and incongruous packaging, and saying “I love it!” when the inevitable prize was revealed. This made my mom feral, which only added to our joy.
Reposted by Captain Awkward
I’m sorry for the things I said when the wrong lights were on
November 13, 2025 at 3:20 PM
I’m sorry for the things I said when the wrong lights were on
Reposted by Captain Awkward
You been hit by a smooth hymnal
What's from Chicago, hates Illinois Nazis, and is holy as fuck?
It's the Pope in 1982.
It's the Pope in 1982.
November 13, 2025 at 4:07 AM
You been hit by a smooth hymnal
Reposted by Captain Awkward
Every office has an executive tier whose emails are like:
saw on news , , can we replce complianc dept with web 3
and a worker tier whose emails are like:
Dear Jim,
First of all, I *love* this idea! Unfortunately, I spoke with Legal and identified a few issues with this approach. For starters…
saw on news , , can we replce complianc dept with web 3
and a worker tier whose emails are like:
Dear Jim,
First of all, I *love* this idea! Unfortunately, I spoke with Legal and identified a few issues with this approach. For starters…
Well, it's a little clearer now why billionaires are so invested in technology that produces better written emails.
November 13, 2025 at 12:10 AM
Every office has an executive tier whose emails are like:
saw on news , , can we replce complianc dept with web 3
and a worker tier whose emails are like:
Dear Jim,
First of all, I *love* this idea! Unfortunately, I spoke with Legal and identified a few issues with this approach. For starters…
saw on news , , can we replce complianc dept with web 3
and a worker tier whose emails are like:
Dear Jim,
First of all, I *love* this idea! Unfortunately, I spoke with Legal and identified a few issues with this approach. For starters…
Reposted by Captain Awkward
Hey so “underage girls” are…children. The word you’re looking for is children. They’re not like, women-in-waiting or women-lite or whatever. They’re children. I think some of you are very uncomfortable with what that means for you but it is still true.
November 12, 2025 at 11:05 PM
Hey so “underage girls” are…children. The word you’re looking for is children. They’re not like, women-in-waiting or women-lite or whatever. They’re children. I think some of you are very uncomfortable with what that means for you but it is still true.
Reposted by Captain Awkward
IT'S '6-7', COOPER. A GENERATION ALPHA TREND. WHAT THEY CALL A 'MAY-MAY'. IT'S AN ORPHANED SIGNIFIER, NO SIGNS ATTACHED. ONE COULD CALL IT DADAIST, BUT SOMME SAY IT'S TOO STUPID TO BE DADA. IT'S ANTI-MEANING, ANTI-HUMOUR, BUT DAMN IF THOSE KIDS DON'T FIND IT A CRACK-UP.
November 12, 2025 at 12:31 PM
IT'S '6-7', COOPER. A GENERATION ALPHA TREND. WHAT THEY CALL A 'MAY-MAY'. IT'S AN ORPHANED SIGNIFIER, NO SIGNS ATTACHED. ONE COULD CALL IT DADAIST, BUT SOMME SAY IT'S TOO STUPID TO BE DADA. IT'S ANTI-MEANING, ANTI-HUMOUR, BUT DAMN IF THOSE KIDS DON'T FIND IT A CRACK-UP.
Reposted by Captain Awkward
Holy shit, just learned about the typewriter art of Montserrat Alberich Escardívol, a Catalan typist. Using an extra wide typewriter and 180 color ribbons, she built up elaborate images from simple characters like 'm' and '.' and ';'. Here is her typewritten painting of the Cathedral of Barcelona.
November 12, 2025 at 4:19 PM
Holy shit, just learned about the typewriter art of Montserrat Alberich Escardívol, a Catalan typist. Using an extra wide typewriter and 180 color ribbons, she built up elaborate images from simple characters like 'm' and '.' and ';'. Here is her typewritten painting of the Cathedral of Barcelona.
November 12, 2025 at 5:35 PM
Reposted by Captain Awkward
Delight of the day: www.tiktok.com/@coach_unc_p...
You must stop being Nonchalant! 🙅♂️ #nonchalant #chalant #emo
TikTok video by Coach Unc
www.tiktok.com
November 12, 2025 at 3:57 PM
Delight of the day: www.tiktok.com/@coach_unc_p...
May your lair be warm and hide you from trouble
November 11, 2025 at 8:28 PM
May your lair be warm and hide you from trouble
Left picture: Before singing to her
Right picture: During singing
Right picture: During singing
November 11, 2025 at 2:42 AM
Left picture: Before singing to her
Right picture: During singing
Right picture: During singing
Reposted by Captain Awkward
pre-writing a devastating obituary for your enemy is god-tier hating of a kind you don’t often see anymore. renaissance haterism. beautiful stuff.
A Sharon Begley byline, almost 5 years after her death.
Upon hearing the news James Watson had died, a STAT reporter said in our Slack, "I wish I could read what Sharon would have written."
Incredible news: Sharon in fact did pre-write a Watson obit. And it is masterful and excoriating.
🧪🧬🧫
Upon hearing the news James Watson had died, a STAT reporter said in our Slack, "I wish I could read what Sharon would have written."
Incredible news: Sharon in fact did pre-write a Watson obit. And it is masterful and excoriating.
🧪🧬🧫
James Watson, dead at 97, was a scientific legend and a pariah among his peers
James Watson, the co-discoverer of the structure of DNA who died Thursday at 97, was a scientific legend and a pariah among his peers.
www.statnews.com
November 9, 2025 at 12:55 AM
pre-writing a devastating obituary for your enemy is god-tier hating of a kind you don’t often see anymore. renaissance haterism. beautiful stuff.
Reposted by Captain Awkward
My latest is a love letter to Chicago. "I see you stumbling through the stubborn, awkward rhythm of showing up, again and again. I see you fighting alongside people who sometimes frustrate and confuse you, and defending neighbors you may have never met, because you know they’re all your people."
In Chicago, We Run Toward Danger Together
"Faced with unrelenting state violence, Chicagoans have refused to be cowed," says Mariame Kaba.
organizingmythoughts.org
November 8, 2025 at 2:46 PM
My latest is a love letter to Chicago. "I see you stumbling through the stubborn, awkward rhythm of showing up, again and again. I see you fighting alongside people who sometimes frustrate and confuse you, and defending neighbors you may have never met, because you know they’re all your people."
Reposted by Captain Awkward
i love this for everyone their mom has interacted with since the 90s
My mum just said to me "You should be hung like a horse". When I challenged her over saying such a thing, it transpires she thought it was a punishment horses got. Turns out she's been incorrectly using the phrase since the 90s in various settings
November 7, 2025 at 7:38 PM
i love this for everyone their mom has interacted with since the 90s
There is so much Wisconsin.
November 6, 2025 at 9:02 PM
There is so much Wisconsin.
Amtrak color study
November 6, 2025 at 6:59 PM
Amtrak color study
Got an amber ring I bought in Gdansk in 1994 resized. I wore it daily for more than a decade and my hand remembers it like it never left.
November 5, 2025 at 9:32 PM
Got an amber ring I bought in Gdansk in 1994 resized. I wore it daily for more than a decade and my hand remembers it like it never left.
Reposted by Captain Awkward
You see how many of these politicians CARRIED in their election races WITHOUT throwing trans people under the bus? Exactly, exactly.
November 5, 2025 at 9:04 PM
You see how many of these politicians CARRIED in their election races WITHOUT throwing trans people under the bus? Exactly, exactly.