Fact: dating is hard.

So hard that if you're 23-year-old rising talent Kyle you opt to bypass actual dating apps like Tinder, which he recently told Billboard felt more like a place you'd sell marijuana than a breeding ground for lifelong romance, and trust in the power of Instagram.

The "Just A Picture" rapper was so disillusioned by the complexity of dating apps, and the unattainable aura of the few fleeting IG crushes that failed to crossover from exchanging "likes" to being cuffed in real life, it inspired his breakout single, "iSpy."

Released in December 2016, "iSpy" debuted at number 80 on Billboard's Top 100 chart before finding its way into the permanent rotation of popular radio stations and racking up plays on streaming sites. By March the song had climbed from 80 to number four, and then number one in early April.

The oddly cartoonish beat and nostalgic, childhood-inspired hook are no doubt part of its appeal, but Kyle and Lil Yachty's natural chemistry also helped cement "iSpy"'s status as a crossover banger. They're just two zany dudes looking for love, and in the case of Kyle, also looking to answer a few of Highsnobiety's most random questions.

Kyle, who is currently working on his third studio album and completing his multi-city "Super" tour, stopped by our office ahead of his show at Webster Hall. Naturally, we put his innate comedic skills to good use with a series of rapid-fire questions, and of course, a Lil Yachty impersonation challenge.

Press play to see if the one they call Super Duper Kyle can actually out-boat the Captain of the Sailing Team.

Also see Kyle and Yachty take their screwball talents to the realm of cartoons in the animated 'iSpy' music video here.

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