Just Plain Cool Movie: “My Date with Drew”

Brian, Drew, and Serendipity

On a lark, I switched the TV over to a movie called “My Date with Drew”, about some guy’s quest to get a date with Drew Barrymore. I figured it would be ok, but probably silly and boring, and within 5 minutes I’d flip over to Sportscenter or something.

But I got drawn in by likable people (including Drew herself), a compelling story, and a positive, life-affirming ending.

The guy is a 20-something filmmaker named Brian Herzlinger who gives himself 30 days to get the date with her, and especially all the various hijinks and crazy schemes cooked up by Brian and his merry band of assistants to make this happen.

I found it impossible not to like Brian. He’s energetic, positive, funny, self-deprecating, yet he thinks he’s a complete loser and will have nothing to say to her, if he can even get the date.

Which requires, of course, that he even gets to talk to her. Here we have the true challenge.

Spoiler alert! Stop reading now if you don’t want to know what happens.

He ends up meeting her at a “Charlie’s Angels” movie premiere, after forging passes to get into the after-party, but chickens out completely after she says “how nice to meet you”. Nice going!

A few days later, his 30 days is up, and it seems like just another one of those “I tried, and failed” stories.

But then a couple of weeks later, the website he had created to enlist help, mydatewithdrew.com, started getting lots of attention. Radio interviews, website interviews, all kinds of buzz pops up.

A few more weeks go by, and then suddenly, he finds out that Drew has finally found out about it. And she loves it. Suddenly, after 3 months, his plan is coming together. So he sets up the date through her business partner, Nancy, for a week later.

After spending a week getting a haircut, working out, and generally spiffing up, he flies to New York for his date with Drew Barrymore at … the “Miracle Grille”. The irony is not lost on Brian.

At the restaurant, he is extremely nervous, waiting for her, pacing back and forth. Then she shows up. And her smile lights up the screen, just like you knew it would.

Let me just pause right here and say I really like Drew Barrymore. She seems like one of the nicest people you could ever hope to meet, in Hollywood or anywhere else. And I’m not normally a big Hollywood kind of guy. In fact, I usually like to rip on Hollywood, especially the blowhards who think they are better than you and me. But she projects an image that is so positive, so life-affirming, so “it’s great to be alive”. She smiles constantly. In that way, she reminds me of my oldest son.

Every movie I’ve seen her in, she pulls off what should be impossible: playing herself, more-or-less, but pulling you into the character anyway. Sheer likability, it seems, can take you a long way on the big screen.

So they have a nice time, and she seems to genuinely enjoy spending time with him. She was worried, in fact, that he would think she was too unreachable and that his feelings would be hurt if she didn’t get back to him. It was a touching moment, with no phoniness or artifice. Call my cynical, but I’m thinking … not that many Hollywood types could pull that off.

Then they exchanged gifts. He got her a Snoopy sno-cone maker, which she loved. And she got him a Sony video camera, so that he wouldn’t have to keep on buying them and returning them 30 days later.

I like the ending a lot. She tells him, and then he tells the audience, that when you have dreams, you should really follow them.

It was cool. The whole movie was just cool. Brian quickly becomes a friend that you’re rooting for, and Drew ends up being even nicer than he, or we, could have ever hoped.

Well worth watching, even if you’re not into “love” stories, which is not really what this is, anyway. It’s about dreams, and the power of believing. And we can all use a little shot of that now and again!

The trailer can be viewed here.


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