5 Gmail Features That Make Me Swoon

My love affair with Gmail is one for the ages. If we were a movie couple, this would be Sleepless in Seattle, but with less Fate with a capital “F,” and more computers. Or When Harry Met Sally, with less Billy Crystal and more computers. Or You’ve Got Mail, with less lies and the same amount of computers. You get the idea.


What I’m trying to say is, Gmail is currently at the “mid-1990’s Meg Ryan” level of American Sweetheart.

On top of the eminently useful labels and filters (read my article for tips on using them, if you haven’t already), Gmail also has a ton of additional offerings that tend to fly under the radar. Here are my top five favorite Gmail features you might not be using yet.

“Undo Send” Button

This is, in my opinion, the most important feature you can enable with Gmail labs. Once enabled, it allows you to retract a sent email within a specified amount of time (five, ten or twenty seconds). You can use this feature to fix typos, include information you may have forgotten, or attach a file that should have been included.

PROTIP: If you use the word “attach” (or some variation thereof) in your email copy, before your email is sent, Gmail will prompt you to attach a file if one isn’t already. I’ve gotten so used to this function, that I always include the word in my emails that will require attachments, just to make sure I trigger that failsafe before I press send.

To turn on the “undo” functionality, go to “Settings, then to the “Labs” tab. Look for the “Undo Send” option and click “Enable.”

undo send


Boomerang is a singularly powerful tool that allows you to schedule emails to be sent at a later time. This is super useful if I want to make sure an email ends up in someone’s inbox first thing in the morning, or if I know I’ll eventually want to send a reminder email, but am worried I might forget about it later.

To install Boomerang, visit: BoomerangGmail.com. Once it’s been activated, a “Send Later” button appears beneath the regular “Send” button when you are drafting emails.


Once you click on this button, a menu pops up allowing you to choose when the email will be sent.


PROTIP: If you send an email that needs a response on or before a specific time, you can set up a Boomerang that will shoot a reminder email to that person if they haven’t responded by your specified deadline. If they do respond within the specified timeframe, the Boomerang email won’t go out.


The starring function is extremely useful for collecting important emails in one place. I use the starring function selectively (instead of automatically starring emails using a filter), which gives me the flexibility I need to keep track of multiple projects and deadlines at the same time. When I’m done with that email, I un-star it to file it back in my regular inbox.

Gmail lets you organize your inbox with several tiers, including “Unread Messages,” “Starred Messages,” and any of the custom labels you’ve created. I’ve organized my own screen to show unread messages, then starred messages, and then my regular inbox.

PROTIP: You can also use different colored stars to demarcate different types of important emails. To activate the additional star types, go into “Settings,” then the “Stars” section of the “General” tab; and drag your chosen stars from the “Not in Use” section to the “In use” section.

Search Function

Most people know very little about how to optimize Google’s general search engine. And when searching within Gmail, there are even more tricks of the trade that will make your search — and life — infinitely easier.

For example, if you want to find an email from a specific person, instead of just typing in their name, write “from:” in front of their email address:


If you want to find an email you sent to someone, write “to:” in front of their email address:


If you want to find all the emails that were sent before a certain date, you can use the date search function. For this one, write “before:” followed by the date in a YEAR/MONTH/DAY format. For example, if I wanted to find all the emails sent before November 6, 1605, then I format it thusly:


If you want to find all the emails sent after a certain date, follow the same format, but substitute “after,” like this:


You can also combine the two search functions to look for emails sent within a certain period. All you have to do is set a “before” and ”after” and separate the two functions with a space:

before:1605/05/06 after:1605/05/04

Calendar Events

Receiving calendar invites through Gmail is especially easy if you also use Google’s calendar tool to schedule appointments and meetings. When you receive an invite, Google provides an option within the email to RSVP for the event.

Gmail has also (somewhat ingeniously) implemented a subtle way to create events from regular emails as well. It can recognize dates and days and use that recognition to prompt the create of calendar events.

For example, say Jessica wants to do lunch with me next Wednesday, and sends me an email asking:


If I hover my mouse over the date Jessica suggested, I’m presented with an “Add to Calendar” prompt:


If I click on the prompt, Gmail and Gcal work together to create the following event description:


Simply adding a time and clicking the “Add to Calendar” button sends the event right to my calendar.

Gmail offers a range of productivity features and smart tools to fall in love with; these are just five that make me swoon. What are your favorites?