The comedic mastermind does more than just entertain, he makes you think. He challenges you. He sends you on an introspective journey inside your own thoughts, to the point where you start to feel awkward. And then he snaps you out of it with the kind of relatable humour that makes your face hurt.

The 30-year-old Polokwane-born self-professed drinker of all the chardonnay, has based When We Were Nearly Young on the theme of transcendence. Transcendence of the fear of dealing with painful things.

He likens these painful moments, the ones that we’re scared to face, to dark rooms in the corners of his mind. He invites the audience into these corners and shares the process he went through to transcend his fear of tackling painful moments.

One thing you will learn early on in the When We Were Nearly Young journey, is that Mogashoa is a deep thinker – sometimes to his own detriment, as he explains – with a knack for absorbing even the smallest details in any situation. He doesn’t just tell stories. He paints elaborate scenes from his past that make you feel like you were there.

Mogashoa wastes no time mincing his words or holding back on details of his sexual escapades. And that is what I found most refreshing about him. He’s honest. But not so honest that it seems forced. His honesty makes his stories relatable. We’re all lazy sometimes, and we all have insecurities. The fact that he is honest about the things that we can all relate to makes you feel comfortable. And then uncomfortable. And then you’re laughing so hard that you don’t know what you’re feeling.

What struck me the most about When We Were Nearly Young is that it is not just stand-up comedy. It’s true stories – told by someone with the incredible ability to see the humour in even the darkest moments in his life – that make you think.

Mogashoa doesn’t tell jokes. He tells – seemingly disparate – stories, which he skilfully weaves into a bigger picture with an even bigger message behind it.

Catch Lebogang Mogashoa in When We Were Nearly Young at Alexander Upstairs until Saturday, 16 May.

For more information and to make bookings, visit the Alexander Upstairs website. Alternatively, connect with them on Facebook and Twitter.

To find out more about Mogashoa’s upcoming shows, follow him on Twitter.