Welcome to Coffee with Carey—where we talk about dating, relationships, and all the weird, funny, hopeful stuff that happens when grown-ups try to find connection.
I’m Carey. I’m a dating coach and matchmaker with over a decade of real-world experience — not someone who crowned themselves a dating expert after two messy breakups and a $39 lighting kit from Amazon. I teach what I know and that’s from working with thousands of clients over the years.
This channel is for anyone who’s ever been ghosted by someone they weren’t even sure they liked, spent an hour writing a thoughtful message only to get “lol,” in response, or needed a reminder that texting someone “Good morning” doesn’t make them your soulmate.
You’re not doing it wrong. But you may be doing it wrong. Check out an episode or two and let’s figure it out.
Oh, and if you need something more personal? The link is around here somewhere.
Warmly,
Carey
Coffee with Carey
What’s the easiest attraction killer?
31 minutes ago | [YT] | 7
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Coffee with Carey
She accidentally flirted with a man in the grocery store today.
Him: *blocking the way to the bananas*
She: pardon me, can I get by?
Him: oh sorry look at me blocking the way. Let me move
She: you’re fine, no worries
Him: thank you, I work out.
She: lololol
1 day ago | [YT] | 45
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Coffee with Carey
What’s the clearest sign someone isn’t ready to date?
1 day ago | [YT] | 37
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Coffee with Carey
What actually builds attraction after the first few dates?
2 days ago | [YT] | 28
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Coffee with Carey
Which early behavior predicts future frustration best?
3 days ago | [YT] | 41
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Coffee with Carey
When someone says “I’m easygoing,” you assume:
1 week ago | [YT] | 55
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Coffee with Carey
Which early-date question would you actually love to ask?
1 week ago | [YT] | 49
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Coffee with Carey
What’s the fastest way a date turns into a chore?
1 week ago | [YT] | 47
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Coffee with Carey
Most of you know I’m in the Chicago area. But we actually have no idea where you all are.
And here’s why I’m asking.
Over the couple years, two couples met right here in my comment section — through me, technically, because I’m a matchmaker — but without me having to lift a finger beyond encouraging people to leave comments and engage. No formal introductions. No profiles exchanged. No behind-the-scenes setup.
They just noticed each other in conversations and kept showing up in the same threads. Curiosity built naturally, and they took it from there.
They’re still dating.
People complain all the time, “There’s nobody near me.” And maybe that’s true. Or maybe it just feels true because you can’t actually see who’s around you.
So here’s the experiment.
If you’re comfortable, drop the major city you live in or near in the comments here. Big city is fine. “About an hour outside of…” works. No need to be specific.
Maybe you scroll and discover there are two or three people near you that you didn’t expect. Maybe that alone shifts something for you. Maybe it inspires you to look a little harder, or differently, than you have been.
This isn’t traditional matchmaking. I’m not pairing anyone up or sliding into DMs. I’m just creating visibility.
If you notice someone nearby and feel like saying hi, do it in the comments. Be respectful, be a grown up, and no bad energy.
Participate only if it feels good to you.
That’s the experiment.
2 weeks ago | [YT] | 65
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Coffee with Carey
What makes you pull back emotionally, even if you like them?
2 weeks ago | [YT] | 49
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