Last week at its annual I/O event, Google launched a new email feature, Smart Compose. Meant to be an extension of the artificial intelligence features already built into Gmail, like Smart Reply and the “important” tag, Smart Compose is the latest example of Google pushing AI into every last part of its empire. After indexing the entire internet for two decades, reading untold terabytes of users’s emails and spending billions on tech to build an AI assistant that can best Apple’s, it makes sense. Google is really good at AI, and they’re making a big bet on it by trying to incorporate it everywhere.

But it’s still not perfect. A few months ago I noticed that Gmail’s Smart Reply feature can totally fail when it comes to deciphering me and my dad.


It’s 2018 and I am a loving son, which means I email with my parents a lot. More specifically, I email my dad really often. Joseph Cosco the Third and I talk over email almost every day. Nearly as frequently I notice funny hiccups with Smart Reply. So when Google rolled out Smart Compose to the masses, I had an idea: Can we stump Google’s newest AI tools like old times? I immediately called him and asked if he wanted to test it out. He obliged.

My dad is a single white man who has spent all of his 54 years living in Upstate New York. He’s pretty cool (used to be a radio DJ) and also a total nerd (his greatest passion is collecting and restoring old arcade games). Our correspondence is typically benign father-son chatter, but there also exists advanced inter-Joe Cosco communication. 

The conversation above that gave Google pause was a fairly wide-ranging one. In a handful of messages, we touched on cryogenics, going to the gym, his ailing achilles tendon and a passing acquaintance he’s told me about a few times. The nail in the machine’s coffin was my dad’s double-exclamation-pointed lament of the treadmill: 


If Google’s finest can’t understand that, there’s no way it’ll be able to follow a chat where we discuss pinball machines by their nicknames, right?

I activated Smart Compose (It’s easy to do in the new Gmail redesign) and waited to see what would appear in my inbox which I could Smart Reply and Compose. For a couple of days, Gmail embarrassed itself with uninspired Smart Replies.


I tend to always ignore Smart Replies, but these seemed especially weak. So much so I was about to call the experiment off due to lack of competition. 

But then, something unexpected happened. Over the weekend I visited my hometown for both my sister’s college graduation and Mother’s Day. I saw my dad for graduation-related festivities on Saturday and we talked about our little experiment briefly. On Sunday, the day of the actual university commencement ceremony, he was a no-show.

On Monday morning I received an email. A link to a listicle about ’60s cartoons and a “it was great to see you Son!” I checked out his link and responded accordingly with an old memory of watching Hanna-Barbera at my grandmother’s house, then told him I missed seeing him on Sunday.

Dad responded by opening up about feeling depressed on Mother’s Day. My grandmother — my dad’s mother — died six years ago on the Monday after Mother’s Day. Just one day short of the exact six year anniversary. He was thinking about her, and he couldn’t shake it. He said he missed seeing me and my two sisters too.

I didn’t know what to say. So I fired up Smart Compose.


Google — with all its infinite wisdom, data, technology and money — was suggesting I call my dad by his first name in the middle of a tense and important conversation about powerful emotions and mental health. 

Instead I ignored Mountain View once again.

It’s unfair of me to expect Google’s experimental product to tackle the heavy-lifting emotional labor of a conversation involving family, death, mental health and parent/adult child relationships. I don’t expect it to do that at all. In fact, I don’t expect AI to help me do anything when I’m writing an email to my dad. We have a quarter century of inside jokes and father-son rapport. I don’t want a machine making pinball puns in my place.

Here’s my review of Smart Compose: it’s fine. It works like predictive text on your texting app of choice and might save you a few minutes writing an email you didn’t care to write anyway. For that reason, Smart Compose can be sort of dumb and do it’s job just fine.

But that means it’s not going to help me write the emails I enjoy most. And if it could, well let’s just say I wouldn’t. 

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