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How To Pick Up Celebrities at TIFF (Very Real And Helpful Tips)

TIFF is upon us, which of course means we will be hanging out with celebrities all week since they are destined to become our new best friends.

Of course, this only works if you successfully strike up a conversation so compelling that instead of gazing upon their free shit, attractive co-stars or important Toronto landmarks, these stars of screens both silver and small gaze upon YOU. And, not to call myself an expert, but one time I met Danny Masterson at the MMVAs and he signed a piece of scrap paper I found.

Stick with me, kids. You’ll go places. Here are 10 foolproof and best conversation starters.

1. “Nice weather we’re having!”
Enter: SARCASM, since this opening can only be used if the weather is abysmal. I mean, picture this: you stroll through the Soho House entrance (because in this scenario you won’t be escorted out immediately), catch the eye of [celebrity you're in love with], toss your hair back—enormous from 40-degree humidity—and say, “Nice weather we’re having!” They will laugh, you will laugh like Julia Roberts in Pretty Woman, and BOOM. How I Met Your Mother, but good.

2. “Excuse me.”
Everybody likes manners, but everybody important likes manners delivered begrudgingly by y-o-u. Maybe it’s been a long day. Maybe you’ve just been dumped. Maybe you’ve gambled away your paycheque. Maybe you know you’ve just eaten a burger that you realized too late was raw. They don’t know. But they will assume the most interesting of any of the above when you need to walk by and say, “Excuse me” like whoever is standing kind-of-in-your-way-but-not-really is a massive inconvenience for you. “Who IS that girl?” they will say. “UGH,” you will respond, rolling your eyes. Ka-ching.

3. “I’m allergic to the sun.”
Absolutely, this sounds insane. But wouldn’t you want to talk to someone whose opening line was their admission of a very inconvenient allergy? Bonus points if you say this while standing out in the sun. (Because if who you’re standing next to calls 9-1-1, you are IN.)

4. “Is this free?”
But sometimes conversations can come from an organic place. Some of us (and I’m not admitting to anything… but yes, me) enjoy things we don’t have to pay for. Some of us also pretend we don’t care about free things when in reality, WE WILL DIE if we don’t get that… what is it? A mechanical spoon? Holy shit. I want that spoon. So, while standing anywhere near anything you want, you force eye contact upon your unsuspecting future life partner and say, “Ohh—is this free?” It probably isn’t. And if it is, it’s not for you. But now they have to tell you, either way, which makes this the most romantic meet-cute of life (made cuter when they buy you the mechanical spoon for Christmas) (Awww!) (How am I not writing movies??).

5. “Um, they’re not movies, they’re fil-ims.”
I’ve never tried this, but I dream of making this declaration to Benedict Cumberbatch after he says “movies” and then he laughs and I laugh and he asks me to grab a drink and I say “Absolutely! But honestly dude, say ‘film’ it’s in the fucking festival title.”

6. “Have you seen this?”
You want the opening line equivalent to sparkling water? (AKA the thing EVERYBODY LIKES?) You’ve found it — the only conversation starter that can go one of two ways: just okay, or hilariously (best case scenario). Exhibit A: You’re coyly loitering outside of a movie theatre, waiting for any famous. One walks by, pauses to adjust their coat, and you say, “Have you seen this?” while casually pointing to a poster. “That’s an ad for cat food,” they’ll say. “Best cat food I’ve ever eaten,” you’ll respond. And everyone knows you don’t leave somebody alone after they say something like THAT (or at least that’s what the manic pixie dream girl effect tells me).

Exhibit B: “Have you seen this?” (doing the exact same thing.) But this time, they laugh. “A cat food poster!” they guffaw. “You’re hilarious!” You are. And this is how you became best friends and/or romantic sexual partners, forever (until the end of the week).

7. “Do you watch Broad City?”
Actually, this is more just a personal filter than a conversation starter. Like, if they do, HELLO, at the very least you’ll sing the show’s praises for no less than 60 minutes. And if they don’t, you’re the cool person who just introduced them to an Important Thing—before avoiding them forever because they don’t watch Broad City.

8. “Is this seat taken?”
Is it getting BOLD in here? No? Still just so humid breathing the air feels like drinking? That’s fine. But imagine the Will Smith-as-Hitch level of coolness you’ll be aligned with when you see a cool person or celebrity eating alone, and you mosey on up and ask, brazenly, in an otherwise empty restaurant, “Is this seat taken?” They’ll look up, slightly annoyed. You’ll sit down, like AC Slater. They’ll become slightly more annoyed. Why? Because it’s Mario Lopez and he thinks you’re making fun of him. (The conversation you have will absolutely be apologizing for the next half hour—but hey. At least there is one.)

9. “I’m tired.”
Just a quick and easy way to relate. Are you alone? Say it loud enough that a few people can hear you. Are you interviewing somebody? Say it so the interviewee feels pressured to keep you awake. Are you in a movie? Say it out loud, after the credits so that afterwards, relieved patrons can look at, smile, and nod knowingly. Be a mouthpiece for the people. Or at the very least, a beacon for anyone who needs a nap.

10. “So I said get me out of this wet suit, and into a dry martini!”
No adult life is complete without this joke, and the sooner we know this, this better for all. So do what I haven’t yet. Say it to someone. Anyone. A normal. A famous. Whatever the B and C list in the Kardashian game constitutes as. Or, better yet, if you’re introducing a movie, I think you’ve just found your opening line. (Cameron Bailey, this is for you.)

Bless.

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