Hey Chicagoland Singles!

As Thanksgiving week approaches, a whole lineup of singles events is waiting for you.

Sure, it’s the season for planning holiday travel, but it might be worth squeezing in a singles event or two before you pack your bags.

Over the next couple of weeks, the city is buzzing with everything from classic speed dating and mixers to scavenger hunts, group runs, puppy-petting socials, and even golf-swing nights. If any of those are your thing, your future boo might be standing right there beside you.

Later this month and into December, you’ll also start seeing events centered around volunteering, salsa nights, and even holiday gift-wrapping for kids. Variety is the name of the game.

And if you’re wondering how to naturally start conversations at activty-based events, don’t worry. I’ve gathered expert tips to help with exactly that. Check out this week’s Tip of the Week below!

So with that being said, let’s move onto the events!

Singles Events Happening This Week

Wednesday, November 12

Thursday, November 13

Friday, November 14

Saturday, November 15

Sunday, November 16

Events Next Week:

Tip of the Week:

This week’s Tip: Conversation-Starters at Specific Activity-Based Singles Events (Where’s Your Boo Edition)

Apart from speed dating and singles mixers, we have a variety of events the next month. So I’ve listed conversation-starters for each of these types of events. And yes, they’re a little cheesy and absolutely the kind of thing your parents would say. But this is ‘Where’s Your Boo?’. Being cheesy is kind of our unofficial love language.

1. Scavenger Hunts

  • “Are you a ‘follow the map’ person or a ‘chaotic energy is my compass’ person?”

  • “I feel like we’d solve these 10 times faster together. Want to form an elite squad of two?”

2. Running Events

  • “Did you wake up excited for this run or were you tricked by a very enthusiastic friend?”

  • “Mind if I jog next to you? My motivation improves by 300 percent when I have company.”

3. Puppy Social Events

  • “Which dog here is definitely the CEO of this event?”

  • “I’m trying to figure out which dog matches my energy. Any recommendations?”

4. Golf / Swinging Events

  • “How long have you been playing? Your swing says ‘experienced,’ mine says ‘please look away.’”

  • “Want to do a mini-challenge? Loser owes the winner a drink… or bragging rights.”

5. Volunteering Events

  • “Do you volunteer a lot or are you here for the moral high ground like me?”

  • “Want to team up on this task? Worst case, we bond over doing it wrong together.”

6. Salsa Dancing

  • “Have you danced before or are you also relying on pure confidence and vibes?”

  • “If you need a partner for the next round, I promise not to step on your feet… much.”

7. Gift-Wrapping Events

  • “On a scale of 1 to 10, how chaotic are your wrapping skills? I’m hovering around a 3.5.”

  • “Want to divide and conquer? You fold, I’ll cut, and we’ll both pretend we’re professionals.”

 

You don’t have to use any of these word-for-word. The point is to break the ice in a way that matches the activity. If it gets a laugh or even a smile, you’re already winning.

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 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!

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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