Ask TSJ: I Want to Crash My Ex’s New Year’s Eve Party

LIFE IS HARD. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. TSJ’s editor, Melissa Bull, and Headshots columnist, Mike Spry, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s incredible question comes from a TSJ reader in Belleville.

Dear TSJ,

I really hope you can get to this before New Year’s Eve, as the question is time sensitive. See, the girl I’m in love with is hosting a huge NYE party at the home she shares with her boyfriend of two years. It’ll be filled with most of our common friends and colleagues. We’ve been broken up for about five years, and haven’t spoken in about 18 months, give or take a drunk text or eight. I’m planning on making a grand romantic gesture and crashing her NYE party and asking her to marry me. I’m thinking part Cusack in Say Anything, part Cusack in Serendipity, part Cusack in Grosse Pointe Blank.

- Riley in Belleville


This one time I was philandering I heard a funny story about John Cusack that someone was telling me as they put their pants on before I never saw them again. This is the story. Philanderer Dude was at some party with some girl — either he was or his friend was, I don’t remember, so let’s just say he was to keep the story simple, yeah? So he was at a party with some girl. And I picture this girl being super short, I don’t know why. But I’m never right about how I picture people. So let’s say she was tall and blonde and Norwegian, because that’s probably true-er. Say she works for a public radio station, even. Now she’s a real person who’s not a real person. So anyway. Philanderer Boy was house partying it up at some shindig with his Fly Norwegian Radio Girl. And who shows up but John Cusack! What! For reals!

Turns out John Cusack thinks Norwegian Girl is super hot and they chat it up a bit at the party. And that’s fun for everyone. Like it’ll make a great story later is what Philly and his dame are thinking. So then clock strikes midnight and Philanderer Boy is all set to go and he gets his and Fly Norwegian Girl’s coats in the basement. ‘Time to call this party a wrap,’ he’s thinking, and he’s also thinking ‘JOHN CUSACK! IN REAL LIFE! WTF!’ And he brings the jackets upstairs and he’s looking around for his Fly Norwegian Radio Lady to give her her pea coat and grab a cab back to his place.

And he sees her leave! WITH JOHN CUSACK! Without her coat! And he’s thinking, ‘What, John Cusack is gonna buy her a coat after they do it? Probably?’

So he’s all like bereft and with this bulkyass Scandinavian coat in his arms and he goes, “Baby!”

What I’m trying to say, Riley, is that no one even listens to Peter Gabriel anymore — not even Cusack. And the only person I know who pulled a Say Anything-Serendipity-Grosse Pointe Blank move was sorely disappointed. He showed up to a married actress in the Hills’ place with flowers and asked her to marry him. And he had to take the train home alone and probably toss the flowers. Though he gets about a thousand points for having the balls to pull that kind of move.

I’ve thought of doing the dramatic I’m here! Let’s do this thing! Once or twice, when I happened to be in Baltimore. But it seemed like a bad idea, and I went thrift shopping instead of potentially turning my life upside down for L-O-V-E. (I got this Mormon-y kind of dress I wound up only wearing once, to a protest.)

Someone else will turn up, Riley. Someone else always turns up. And then you’ll be picking out your wedding flowers and getting your Beyonce on. And it’ll be pretty cool.

So, yeah. Nix that party. Go to another one.




Dear Riley,

There are two things that have ruined the notion of love for a generation: John Cusack (as Chuck Klosterman argued) and New Year’s Eve. So, you know, way to make a time bomb by combining the two.

Look, there’s no way that this unrequited love ends well—for you. it has colossal failure written all over it. So, my advice? Go for it. Go big. Go full-Cusack on that poor woman. The worst that happens, and there’s a 99.99999992% chance that it will, is that your epic rejection in front of friends and colleagues shames you into moving on.

Good luck,

Got a question for Melissa and Mike? CLICK HERE and fire away. If we use it… your life will improve immediately. 

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