We’re not even in the peak of winter yet, and somehow Chicagoland is already threatening us with sub-zero temps ❄. Sure, the weather makes it tempting to stay home with hot cocoa and a weighted blanket, but the truth is, there’s something even hotter happening right now: the singles events lineup for the next few weeks.

More and more IRL singles events are popping up, and they’re arriving in every flavor imaginable. From Ugly sweater parties, swanky dinners, cold plunges, to trivia nights, dating events are no longer old-fashioned. As December rolls on, you’re almost guaranteed to find something that matches your vibe, and maybe even a Boo who matches your interests.

If you’re new here, you should know that from time to time I drop little tips and tricks to help you navigate the dating scene with less stress and more charm. After a short hiatus, I’m pleased to announce that the Tip of the Week is officially back. This week, I’m sharing a few conversation openers you can use at ugly sweater parties or honestly any singles event you wander into.

Check those out below! And now, let’s get to this week’s events!

Some events may not share certain criteria like age ranges. If you would like to be certain, please reach out to the organizers of the events you are interested in attending. Also, certain event titles below may state ‘SOLD OUT’. In some cases that is not true. Please ensure to visit the event listing site to confirm.

Tuesday, December 9

Wednesday, December 10

Thursday, December 11

 Friday, December 12

 Saturday, December 13

Sunday, December 14

Events Next Week:

Tip of the Week:

This week’s Tip: Conversation openers for this month’s singles events

For the different types of events this month, I’m sharing conversation openers that you could use in those respective events. (Warning: using these openers may lead to first dates with potential Boos)

1. Volunteer Evenings
“What made you pick this volunteer event out of all the holiday chaos happening right now?”

2. Mixers at Bars & Lounges
“What’s your go-to move when you walk into a place like this? Dive into the crowd or observe the chaos first?”

3. Speed Dating
“If we had one extra minute beyond the timer, what would you want to talk about?”

4. Ugly Sweater Parties
“So what’s the story behind your sweater? There’s always a story.”

5. Curated Dinners / Swanky Singles Nights
“If you could magically add one dish to tonight’s menu, what would it be?”

6. Holiday Happy Hours
“Alright, settle this: what’s the superior holiday drink? And why is it not eggnog?”

7. Sauna / Cold Plunge Socials
“On a scale of 1 to 10, how questionable do you feel your life choices are right now?”

8. Coffee Shop Speed Dating
“If you could only drink one coffee for the rest of winter, what’s your pick?”

9. Fitness / Run Events
“So what’s your cheat meal you pretend not to have?”

10. New Year’s Eve Singles Parties
“Are you here to find a midnight kiss, or are you here to witness everyone else panic about it?”

If you feel these openers land high on the corniness scale 😂 , don’t stress. Most of the time, a simple “Hey, how’s it going?” works perfectly. Once the conversation starts flowing, your own humor, quirks, and charm do the real heavy lifting anyway.

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And a Sneak Peek into a Few Events Coming Up in the following weeks:

Where’s Your Boo is also partnered with Variants.

Looking for a word game experience with a modern twist? Well, look no further! Variants sharpens your mind just like other popular word games, but the challenge is different. Guess the five words with a special constraint!

Click here to play!

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!

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