Olivia Dean Delivers Lessons in Love and One Hell of a Show at Madison Square Garden

By Larisha Paul

Larisha Paul

There’s a word Olivia Dean consistently called to mind throughout her headlining performance at Madison Square Garden on Friday, Aug. 14 — present. The show was the first of four consecutive sold-out nights the British singer-songwriter has scheduled at the venue this weekend. She didn’t seem to be thinking too much about the other three, or really anything beyond that exact moment. Dean was astoundingly present. 

It’s the most apt descriptor for the manner in which she commanded the room for nearly two full hours with a set spanning 24 songs. “I’m feeling emotional and grateful and so present with you this evening, New York,” Dean told the audience. It was early in the night and she just finished introducing the show with an opening run of “The Art of Loving,” “Nice to Each Other,” and “Lady Lady.” A brief encapsulation of how love lingers. A madly persuasive plea to live in the moment. A surrender to the inevitability of change. It was the exact order in which the songs appear on her acclaimed second album, The Art of Loving, which shares a title with the tour.

For a moment, it seemed as though the set list might directly mirror the record’s track list. The Art of Loving, after all, is an album best consumed as one whole, indulgent piece. Each track flows so effortlessly into the next it feels sinful to tear them apart. This makes for a dependable and familiar listening experience, but would be far too predictable to support the lessons in love Dean was set on delivering throughout the night. Unlike the fixed order of these songs, life and love are perpetually at the mercy of the present. They’re capable of changing drastically from one moment to the next. Dean knows this because she’s seen it. 

“We were here just maybe nine months ago, supporting Sabrina Carpenter, and it’s crazy to be back headlining now,” Dean said, referring to her opening slot on the pop star’s Short n’ Sweet tour. “I’m in awe of how much can happen in such a short space of time.” The non-exhaustive sum of events within this time frame included winning Best New Artist at the Grammy Awards and scoring two Top 10 hits on the Billboard Hot 100. She might not have believed it if you’d told her then what awaited her in the future. But watching her on that stage, statuesque in a gold gown, it was impossible to imagine any other outcome. 

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Dean glided across the stage with palpable charisma during “So Easy (To Fall in Love),” then racked her mind for the warning signs she might have missed, or mistaken for nerves, on the piercing ballad “Close Up.” Every few songs, she recentered the room with speeches that encouraged sweeping introspection. Before she twisted the knife even deeper with “Let Alone the One You Love,” it was time for one of those requisite lessons in love. “Don’t let anyone ever hold you back and tell you they love you at the same time,” Dean said. Her tone was stern, as though she learned this the hard way and wanted so badly to soften the blow for someone else. There were upwards of 17,000 people in the audience. If only one of them needed to hear those words, then Dean had done her job. 

Her next sermon came just before “Messy,” the title track of her debut album released in 2023. “The moment that I just let go and allowed life to be the way it was going to be was the moment that I just started enjoying myself again,” Dean said. “So this song is like my lullaby, but it’s a song for you, too. I hope you feel present with me now.” The synergy amongst her band affirmed how freeing it must have been to detach from her hardened perfectionism. Dean was joined by two backing vocalists with striking range; her long-time pianist, bassist, guitarist, and drummer; and a masterfully assembled three-piece horn section. There was a fluidity to their performance that treasured passion over technical precision. 

Midway through the set, Dean went solo as she settled at a grand piano stationed on the far left side of the stage. This wasn’t typically part of the show. “I don’t normally do this, but I like New York,” she said. Dean spoke briefly about Growth — both the EP she released five years ago and the act of emergence — before playing the opening notes of “Slowly.” The past was painted clearly on her face as she sang: There’s a line about remembering someone calling two cabs, one for her and one for him, before realizing he rode his bike that day. Eyes shut, Dean was wholly present in the memory. “Maybe I will be fine,” she sang softly as she closed out the track. She sat still for a moment, present in the present once again. 

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The same reflective look flashed across the faces of the audience as Dean launched into the ruinous “Loud” on a B-stage toward the back of the arena. The song is one of the most devastating moments on the album because of the way it so plainly illustrates the collapse of a relationship through minute details — to begin with four hands at the piano and end with only two. It’s the most affecting moment of the show. Dean elevated the record to stratospheric heights through the sheer force of her voice. It sliced right through the thousands of voices singing along in a chilling display of control and magnetism. Dean leaned further into the pull she had on the audience during “The Hardest Part” as she made her way back to the mainstage through the crowd while the whole room clamored to get closer. 

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