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Hey Chicagoland Singles!

We’re 11 days away from Halloween!

You know what that means? We’re 10 days away from figuring out what our Halloween Costumes will be!…….Just kidding!

Sure, it might not be your top priority right now, but if you’re heading to any Singles Halloween parties next week, it’s worth giving your outfit a little thought. After all, throwing together a Labubu costume overnight isn’t exactly for the faint of heart.

Fear not however! As your Boo-finder concierge, I’m here to speed things up. I’ve put together a short list of costume ideas that are unique, and more importantly, great conversation starters with your potential Boo! (Keep reading)

And hey, if you want to keep the planning to last minute, no judgement here! The list will also contain last-minute, easy-too-pull off costume ideas too.

I”m guilty of last minute planning too! Just look at my college Halloween costume for proof:

The Mummy Returns! (Craftsmanship sponsored by Charmin.)

Either way you approach it, get excited because we have a lot of events leading up to Halloween. Let’s get to it!

Singles Events Happening This Week

Thursday, October 23

 Friday, October 24

 Saturday, October 25

Sunday, October 26

 Events Next Week: 

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Tip of the Week:

This week’s Tip: 20 Halloween Costume Ideas (Singles Events Edition)

You might be wondering, what’s a costume idea that will make me look attractive to my future Boo?? ……..Any day of the year, that would be the right question. Not for October 31st my friend.

This is the one day of the year, you are allowed to look funny and interesting at a Singles event.

Just like at any singles event, you want to create a connection. And that doesn’t change because it’s Halloween. So that’s why, I’m sharing 20 costume ideas below that just might do the trick.

Costume ideas that require some effort:

  • The Green Flag – Green outfit, tape on phrases like “has emotional intelligence” and “actually listens.”

  • The Red Flag – Red everything, tape on lines like “says not ready for a relationship” or “texts ‘u up?’ at 2 AM.”

  • Retro Space Tourist (2050 Edition) – Silver jacket, helmet, boarding pass for “Mars Airlines.”

  • Oppenheimer + Barbie Crossover (“Barbenheimer”) – Suit up in half pink, half gray.

  • Cupid’s Intern – Pink outfit, tiny bow, fake HR badge that says “Romance Department, Trainee.”

  • A Dating App – Wear a giant phone screen costume with a cutout for your face (your “profile pic”), and use the lower half for your bio.

  • Parking Enforcement Officer – Neon vest with a fake parking ticket.

  • Netflix Recommendations Page – Poster board with movie/tv show thumbnails, arranged like how it appears on Netflix.

  • Walking Spotify Playlist – Cardboard costume with a QR code linking to a real playlist you made for the party.

  • Google Maps – Dress in cardboard, show a map of Chicago, with arrows and an eta to your favorite restauarnt for a first date 😆.

Last-Minute Costume Ideas:

  • Error 404 Costume Not Found – Plain white T-shirt, write that exact phrase in Sharpie.

  • Zoom Meeting – Formal on top, pajama bottoms below. Hold a fake coffee mug, say “you’re on mute.”

  • Netflix and Chill – Write “Netflix” on your shirt, carry an ice pack.

  • Spotify Wrapped: 2025 Edition – Write your top 5 “bad decisions” of the year on your shirt.

  • Cereal Killer – Tape mini cereal boxes on yourself, add plastic knife.

  • Budget Superhero – Bath towel cape, duct-taped logo.

  • Midwest Vampire – Regular outfit, plastic fangs, hold a Busch Light.

  • “Hot Takes” – Write random controversial opinions on sticky notes and wear them. (“Pineapple belongs on pizza.”)

  • Unread Emails – Wear white, tape “1,287” in red bubble to your chest.

  • The Mummy costume - It’s tried, tested ( by me 😄), and let me tell you, it won’t disappoint! Only requirements: toilet paper and tape.

If none of these work for you and you’re still stuck on ideas, no pressure. Going without a costume to a Halloween party is totally fine.

Know a single friend who’d love Where’s Your Boo? Forward this email to them, or send them this link to sign up!

And here’s a sneak peek into November:

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That’s it for this week.

And as always, thank you for reading another edition of Where’s Your Boo?. Your boo is waiting for you. So get out there, and let us know how it goes!

And for more, subscribe to Where’s Your Boo?

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