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DATING IN 1999 vs. 2019

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Smosh takes a twenty-year swipe at how people actually meet, flirt, and ghost each other.

Smosh’s latest sketch, “DATING IN 1999 vs. 2019,” lines up two eras of courtship side by side and lets the gap speak for itself. One half plays it painfully sincere — landline calls, Titanic-quoting pickup lines, actual in-person nerve. The other half is all thumbs, screens, and the blunt honesty of app-era dating. It’s broad, it’s silly, and it’s built on a format the comedy collective has been running for years.

• The sketch belongs to Smosh’s recurring “then vs. now” format, following earlier entries like ‘1997 VS 2017’ and ‘PARENTS IN 1998 vs. PARENTS IN 2018’.
• The 1999 side leans on earnest, pre-internet courting rituals — personal landline calls, in-person etiquette, and a cheesy Titanic reference (“I’ll be your Jack, you be my Rose”) — while the 2019 side runs on smartphone culture, dating-app etiquette, and blunter relationship expectations.
• The video landed in August 2019, shortly after Smosh’s acquisition by Rhett and Link’s Mythical Entertainment in the wake of Defy Media’s sudden collapse.

A Franchise Built on Generational Whiplash

Smosh didn’t invent the “decade gap” bit, but the channel has turned it into a dependable house style. “1997 VS 2017” mined the same vein for general nineties nostalgia, and “PARENTS IN 1998 vs. PARENTS IN 2018” narrowed the joke to parenting styles. “DATING IN 1999 vs. 2019” is the format’s logical next target: courtship is one of the few subjects where the technological jump — from rotary phones to Tinder — is instantly visible and instantly funny without any exposition needed.

The structure lets the writers set up a punchline in the first half of a scene and pay it off twenty years later, usually by having the exact same beat play out with opposite tools. A move that reads as romantic in 1999 — showing up unannounced, quoting a movie, waiting by the phone — becomes either baffling or a red flag once it’s dropped into 2019’s texting norms.

Landlines, Titanic Lines, and In-Person Courting

The 1999 segments lean hard into the earnestness of pre-smartphone dating: a suitor calling a shared family landline and hoping a parent doesn’t pick up first, a date planned entirely through spoken conversation, and courtship etiquette that assumes you’ll actually see the person’s face before anything gets decided. The signature bit is the Titanic-quoting pickup line, a direct nod to the movie that had basically colonized the entire culture’s idea of romance two years earlier.

“I’ll be your Jack, you be my Rose.”

It’s a small line, but it’s doing a lot of work — it’s the sketch’s shorthand for a whole era where big, sincere, movie-quoting gestures were the currency of flirting, long before anyone had to worry about a screenshot.

Swipes, Apps, and Realistic Expectations

Flip to 2019, and the sketch’s version of dating is governed by app etiquette, group-chat vetting, and expectations calibrated by a decade of swiping fatigue. The humor comes from how procedural it’s become — matching, texting, scheduling, and bailing are all mediated through a phone screen instead of a phone call, and nobody in the sketch pretends a first date is destiny the way the 1999 characters do.

That contrast — sincerity versus efficiency — is the engine of the whole bit. The 2019 characters aren’t colder, exactly; they’re just operating with information the 1999 characters never had access to, from profiles to read receipts, which changes what “getting to know someone” even means before two people are in the same room.

A New Home at Mythical Entertainment

The timing matters. Smosh released the sketch not long after Defy Media abruptly shut down, a collapse that put the future of Smosh’s entire back catalog and production pipeline in question. Rhett and Link’s Mythical Entertainment stepped in to acquire the brand, and “DATING IN 1999 vs. 2019” arrived as part of the channel’s push to keep its recognizable sketch formats running under new ownership without missing a beat.

Smosh has built a lot of its identity around comparisons like this one — the kind of pop-culture-adjacent territory that’s also fueled pieces like who fans think certain stars should date next or a look back at a celebrity’s relationship history, where the joke or the interest is always in how much norms shift when you stack one era against another.

The sketch doesn’t pretend either decade wins. 1999 gets the sincerity, 2019 gets the honesty, and the Titanic line stays the funniest thing in either half — which, twenty-two years after the movie came out, is its own kind of punchline.