THE PICKUP ARTIST Review: Alvaro Orlando Delivers a Surprisingly Heartfelt Dating Comedy

Alvaro Orlando writes, directs and stars in a dating comedy packed with laughs, vulnerability and an unexpected amount of heart.

THE PICKUP ARTIST is one of those movies I kept hearing about but, for whatever reason, took me a while to finally check out. I went into it without many expectations, and I am honestly glad I did because this might be one of the most pleasant surprises I have had with an independent film lately.

Inspired by real-life experiences, THE PICKUP ARTIST brings humor to the unpredictable world of modern dating while exploring something almost everyone can relate to: the search for a genuine connection. What caught me off guard was just how sincere the movie becomes while still being genuinely hilarious.

This is not simply a movie about guys learning how to talk to women. It is about heartbreak, friendship, confidence, insecurity, and all the ridiculous things people convince themselves they need to become when what they really want is for someone to accept them.

The story follows Drew after an unexpected breakup forces him to question everything he thought he knew about relationships. Suddenly thrown into modern dating, Drew navigates attraction, romance, and a series of increasingly unpredictable situations while trying to figure out what he actually wants.

Even if the setup sounds familiar enough, THE PICKUP ARTISTquickly proves it has much more personality than its premise suggests.

Alvaro Orlando Is THE PICKUP ARTIST

Alvaro Orlando writes, directs, and stars as Drew. Whenever someone takes on all three of those jobs, I am immediately curious. It is a bold move because you are essentially putting the entire movie on your shoulders.

In this case, Orlando absolutely is this movie.

I wasn’t familiar with his previous work before watching THE PICKUP ARTIST, which might have made the experience even better. This was my introduction to Orlando, and he had me within the first few seconds.

His performance has heart, sincerity, vulnerability, hilariousness, and plenty of swagger. Drew can be confident one minute and completely lost the next, yet Orlando somehow makes those sides of him feel like parts of the same person rather than different versions of a character.

Something about the journey, the performance, and how genuinely the movie wears its heart on its sleeve completely won me over.

It becomes even more interesting knowing that Orlando has a real connection to the pickup-artist world. He previously competed on and won the first season of VH1’s THE PICKUP ARTIST, which gives this fictional story an unusual authenticity. You can feel that Orlando understands the world he is making fun of, but he also understands the men inside of it.

Drew never feels like a punchline. Instead, the comedy comes from watching a guy desperately try to figure himself out while everyone around him seems convinced they already have the answers.

Drew And Cocksberg’s Friendship Feels Real

Andrew Lewis Caldwell plays Drew’s best friend, Cocksberg, and throughout the movie I kept asking myself where I recognized him from. Then it finally clicked: Spider-Noir.

Caldwell and Orlando make a fantastic best-friend duo.

Their friendship might actually be one of my favorite elements of the entire film because it feels lived-in. They have the kind of chemistry where you believe these two have years of stories together that happened before the camera ever started rolling.

This Pickup Artist especially hit home for me.

So many conversations, nightlife scenarios, and ridiculous situations between these guys reminded me of my own early-20s experiences. Anyone who spent those years going out with close friends, navigating relationships, getting terrible advice, giving even worse advice, and somehow surviving the night will probably recognize pieces of themselves here.

With so much relatability built into the story, the movie’s comedy feels even stronger because so many of its funniest moments come from situations that feel instantly familiar.

Some moments are laugh-out-loud funny because they don’t feel like manufactured comedy setups. They feel like stories your friend would tell you years later that somehow became even funnier with time.

Evan Ross Brings The Swag As Havok

Then there is Evan Ross as Havok. Ross brings exactly the kind of presence this movie needs. Havok is charismatic, highly likable, and mysterious at the same time. He enters Drew’s life as a pickup-artist guru who seems to understand attraction, confidence, and human behavior better than anyone else around him.

Naturally, there is more underneath that surface. Ross gives Havok enough swagger that you understand why Drew would listen to him, but he never makes him feel like a cartoon version of the stereotypical dating guru.

That is another thing I appreciated about THE PICKUP ARTIST. The movie gives us a surprisingly wide range of men and different ideas about masculinity, dating, and relationships.

Some guys think confidence solves everything, others hide behind jokes, some are looking for love or attention, and some probably do not even know what they are looking for yet.

Drew is stuck somewhere in the middle, trying to decide which voice he should actually listen to.

Leslie Lluvet Makes Molly Almost Too Easy To Hate

Then we have Molly, played by Leslie Lluvet. I could not stand Molly from beginning to end. And I mean that as a compliment to Lluvet.

She delivers the kind of performance where you recognize this person immediately because most people have probably encountered some version of Molly at some point in their lives. Whether it was someone they dated, someone their friend dated, or simply somebody they watched completely derail another person’s confidence, the behavior feels painfully familiar.

Lluvet commits to it.

You immediately understand how Drew reached the emotional place we find him in, and the performance gives his journey an important foundation. Without believing the breakup and the emotional damage behind it, much of what follows would not work nearly as well.

Then Alexis Knapp comes into the film and brings an entirely different energy.

Knapp is one of the lights of the movie. Her presence gives the story warmth and helps balance some of the chaos surrounding Drew. Her performance has an ease that works especially well against Orlando’s nervous, constantly evolving energy.

The movie becomes stronger whenever it slows down long enough to let its characters simply connect.

That is ultimately what the entire story is about anyway.

The Pickup Artist Is A Dating Comedy That Actually Feels Lived-In

What surprised me most about THE PICKUP ARTIST is how much real life it packs in.

There are ridiculous situations, unexpected turns, romantic complications, and plenty of comedy, but underneath it all are recognizable experiences.

Bad relationships, great friendships, awkward conversations, nightlife, heartbreak, confidence, jealousy, and attraction all shape the experience. Then there is that uncomfortable period after a breakup when everyone around you suddenly becomes an expert on what you should do next.

The chemistry across the cast sells it all.

The movie also understands something important about modern dating: everybody wants genuine connection, but people have become very good at making finding it unnecessarily complicated.

Drew initially thinks he needs to become somebody else to succeed. He needs better lines, more confidence, more swagger, and a completely different approach to women.

Yet THE PICKUP ARTIST gradually becomes much more interested in whether Drew can simply become comfortable being Drew.

Orlando’s performance shines most with his vulnerabilty.

For all the comedy surrounding him, there is something very sincere about watching this guy get knocked down emotionally and slowly rebuild himself.

The movie doesn’t reinvent every romantic-comedy idea we have seen before, and it enthusiastically embraces some familiar genre territory. What separates it is the personal nature of the storytelling.

It feels like somebody telling you stories that actually happened, even when the movie is obviously heightening them for comedy, giving THE PICKUP ARTISTits identity.

Verdict

I did not expect to connect with this movie the way I did. I definitely did not expect to finish it, stand up in my living room, and applaud.

Yet here we are.

TTHE PICKUP ARTIST is funny, heartfelt, vulnerable, and surprisingly personal. Alvaro Orlando gives everything to Drew while proving himself to be a filmmaker and performer I absolutely want to see more from.

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