In March, Taylor Swift posted some photos from her trip to an undisclosed tropical location with then-boyfriend Calvin Harris. One caption read, "That time we finally took a vacation." This summer, Swift went on another jaunt with a new boyfriend and a group of girlfriends. Elle covered the resulting high jinks with a piece titled, "That Time Cara Delevingne Scared the Sh.t out of Taylor Swift and Tom Hiddleston."
The expressions "that time I" and "that time when" have bubbled up all over the internet, in headlines, in promotions and on social media. Just recently, there was "That Time When Johnny Depp Looked Just Like Justin Bieber" and "That Time I Stumped a Gallup Pollster."
It's a strange construction, one that doesn't make much sense. Why wouldn't Swift just write, "We finally took a vacation?" Why tack on an unnecessary grammatical flourish?
The answer has to do with the way users have reshaped language online. "That time I" works in real time to make readers feel like they're part of an in-group, creating collective nostalgia for events that just took place. In some way, it's a neat linguistic trick. But when we're nostalgic for things even as they're happening, do we miss out on actually experiencing the things we're so excited to share?
Like most digital language innovations, "that time I" started with teenagers. Teens have been using variants of this construction — "that feel when," "that awkward moment," "that awkward feeling" — to describe painful moments for years.
The expression gave people a way to universalize their experiences, making the faux pas of growing up seem less personal and painful. As linguist Gretchen McCulloch explained to Thompson, "It's saying, 'this thing has happened to me, this has happened to me before and this was my reaction, it's probably happened to other people and they've also reacted the same way."
The phrase spread to non-teenage users and evolved into new versions. Around 2011, "that time I" began popping up on Twitter, along with "that awkward moment" and "that feeling when," to tell stories of discomfort or angst.
Eventually, "that time when" grew into a distinct phrase, separate from the rest of the "that awkward feeling" family, although still sometimes used interchangeably. Now it often describes a real event happening in the world, something surprising, awesome or terrible, often accompanied by a video or an image — only the intimacy and urgency of teen life are still inherent in the phrase.
What makes "that time I" so appealing? As Northwestern University linguist Gregory Ward explains, it's the demonstrative "that," which often signals a common, shared knowledge or reference between a speaker and a hearer. "That dog kept me awake last night," for example, implies that the dog has been mentioned before. Using "that," Ward says, creates a sense of closeness.
Yet, as used online, the locution usually refers to an experience not shared between the writer and the reader. In fact, the expression is often deployed as a framing device for obscure, bizarre or personally meaningful information that the reader would otherwise have no access to: Swift's beach vacation.
The intimacy created by "that time when" is a warm, engulfing fog, with no use at all for grammatical and logical scaffolding. Without having been at Swift's party — and without the construction of the sentence reminding us that we weren't there — we can all feel like we're part of the squad. Used by celebrities, and not by teenagers, it's a way of creating a false sense of relaxed togetherness that is also a branding exercise. It's easier to sell makeup or clothing to people who think of themselves as your friends, even if you'll never meet them IRL.
There's something ersatz about our weird online nostalgia for very recent events. In that sense, "that time when" is extremely useful, hugging the recent past and a speaker's audience close in a way not many other phrases do. And yet it heightens the disturbing slipstream effect of internet time, where we never feel quite in the moment, instead always observing it through various mediating devices, recording it, time-stamping it, commenting on it, as it fades away as surely as one of Taylor Swift's boyfriends.