After 19 years and more than 26,000 events, our hosts have stories. Not the kind that go in a data report. The other kind. The ones that come out late in the evening, when someone asks, "What's the strangest thing you've ever seen?"
We're sharing some of them, and not to poke fun at anyone. Every person in these stories walked into a room full of strangers hoping to meet someone, which is braver than most people manage on a Tuesday. We're sharing them because dating does something to people. It brings out the nerves, the hope, the over-preparing, and every so often, the truly unexpected. You'd never see these moments at the dentist or the hardware store. You see them when the stakes feel personal.
We've sorted them into three rounds: the moments our hosts saw in the room, the messages that landed in our inbox, and the small details guests noticed that we never saw coming.
🚪 ROUND ONE: In the Room
📄 The Man With the Pamphlet
Host: Yvonne, Chicago
Most first-timers arrive with a few talking points and a nervous smile. One gentleman in Chicago arrived with a pamphlet. About himself. He left a copy at every table.
What it tells us: He wanted to make sure nothing important got left out. That's the most common first-timer instinct there is: the fear that a few minutes won't be enough to show who you are. The irony is that the best conversations at our events are the ones nobody could have written down in advance. As our hosts put it, the less it sounds rehearsed, the better people do. Still, we'll admit it. He was memorable.
🍸 The Drinks That Weren't Included
Host: Lorena, Washington, DC
Two women at a DC event ordered a round, then declined to pay the venue because they believed drinks came with the ticket. They didn't. To keep the night moving, we covered the tab and later asked for it back.
One of them replied that rather than asking to be reimbursed, we should be apologizing for the confusion. She added that we ought to list everything the event doesn't include.
What it tells us: Expectations are half of any night out, and first dates are no different. When something isn't spelled out, people fill the gap with what they hope is true. Point taken on clarity. Though a complete list of everything an evening doesn't include would be a very long page.
⏱️ Sixteen Women, Eighteen Men, and Ten Minutes
Host: Megan, Seattle
One Seattle event came in at 16 women and 18 men, so a couple of the men took turns sitting out each round. The next day, one gentleman emailed to ask for a refund. He had sat out ten minutes.
What it tells us: When you're nervous and hopeful, every minute feels like it counts. Maybe the round you missed was the one. Balancing a room is the least glamorous part of a host's job, and it's the part guests notice most when it's even slightly off.
📝 The Most Thorough Review We've Ever Received
Host: Megan, Seattle
Another Seattle guest wrote the morning after to say she'd enjoyed the event, the hosts, the venue and the appetizers. Then came the notes. The hosts she met weren't pictured on our website. The site didn't have much information about Seattle itself. And she had discovered that our hosts don't go into an office every day to prepare.
What it tells us: She had a lovely night and still went looking for the fine print, which is how a lot of us approach dating now. Great evening, but let me check the details. For the record, our hosts do prepare. They just don't need a desk to do it.
📬 ROUND TWO: From the Inbox
🚿 The Shower Question
From our inbox, New York
Our website once promised that our hosts would "shower you with attention." One New York gentleman wrote in to ask whether that meant he'd be showering with the hosts. When we explained that it did not, he had a follow-up question: would he be showering with the guests instead?
What it tells us: Copywriting is harder than it looks. Also, you have to admire the optimism.
☎️ The Wrong Number
From our inbox
One guest wrote in, very upset. She'd called our office several times and kept reaching a sex line. How could a reputable company list a number like that? We suggested she might have misdialed, which only upset her more. Our number is 866 WE SPEED (866-937-7333). She had been dialing 877.
What it tells us: When you're nervous about something new, every small snag can feel like a sign. For the record, it's 866. Please double-check before you dial.
🍝 Is the Meal Included?
From our inbox
We invited one guest to try our matchmaking service, completely on us. His reply: would the meal be included too?
What it tells us: It never hurts to ask. It just sometimes makes the office laugh.
🤖 The Personal Reply That Wasn't Enough
From our inbox
One of our assistants personally wrote to confirm a guest's reservation. The guest wrote back to ask whether she'd also be receiving the automatic confirmation from the website.
What it tells us: We've spent 19 years insisting on real people over robots. Sometimes people just want the robot too. We get it. Receipts are comforting.
✍️ Everyone's a Blogger
From our inbox
We don't allow writers to cover our events, because guests deserve to date without ending up in someone's post. One aspiring attendee who blogged took the news philosophically. Most people are bloggers these days, she warned, so if we kept this up, we might soon have very few guests left.
What it tells us: Privacy is part of why people feel free to be themselves in the room. Nineteen years later, the rule stands, and so do the guests.
🍽️ ROUND THREE: The Details Nobody Expected
🥩 The Vegan at the Steakhouse
From our team
One guest was upset that there didn't seem to be any vegan appetizers. The venue was STK, whose tagline is "Not your Daddy's Steakhouse." Not your daddy's, perhaps. Still very much a steakhouse.
What it tells us: Fair enough, dietary needs matter, which is exactly why we typically don't serve food at our events. But when the venue has "steak" in the name, we'd gently suggest eating beforehand.
🎧 The DJ Review
From our team
One guest emailed the next day with feedback about the evening. Among her notes: the DJ at the club didn't scratch well, and he repeated songs.
What it tells us: People bring their whole selves to a night out, including their standards for turntablism. We don't hire the DJs. We did pass along the note, in spirit.
📏 The Tables Had Notes
From our team
One guest was troubled that the tables were different heights and seemed to be placed in random order. Another wrote in about a mystery that had clearly stayed with him: there was a table with only a table number on it. What was that about?
What it tells us: Nerves make people notice everything. When your heart's racing, the furniture becomes part of the story. The table number, for the record, was so you could find your table.
🍤 The Appetizers Weren't on the Menu
From our team
One guest did her homework. She read the restaurant's menu before the event so she'd know what to look for. When the complimentary appetizers arrived, they weren't on it, and she asked for a refund. The reason they weren't on the menu: the kitchen had made them specially for our event.
What it tells us: Preparation is a great instinct. Sometimes the best thing on the night is the thing you couldn't have planned for. That goes for appetizers, and it goes double for people.
🔔 No Bells, No Whistles, No Name Tags
From our team
Our events are deliberately relaxed. No bells, no whistles, no name tags, and we say so right on our website. One guest and her friend arrived, found no bells or whistles, and left. The relaxed atmosphere, she explained, made her uncomfortable. Another guest was upset that there were no name tags and no loud signal when it was time to switch tables.
What it tells us: Some people find structure comforting, and that's completely valid. It just helps to read the fine print, especially when the fine print is the headline.
❓ Your Speed Dating Questions, Answered
Are drinks or food included at a speed dating event? Typically not. Guests order their own drinks at the venue, and because everyone's dietary preferences are different, we don't usually serve food. Some venues choose to offer appetizers, and some invite-only events include them. Check your event details before you go.
What happens if there are more men than women, or vice versa? When numbers are uneven, guests take turns sitting out a round. Most people use the break to visit the restroom or enjoy the venue. Your host manages the rotation, so you don't have to.
Are there name tags, bells or whistles? No. MyCheekyDate events are host-led and deliberately relaxed, with no name tags, bells or whistles. Your host lets you know when it's time to switch tables. See how our events work.
How long is each date? Each conversation lasts about four to six minutes, depending on how many people attend. Then you move to the next table.
Should I eat before speed dating? It's a good idea. We typically don't serve food, since everyone's dietary preferences are different. Some venues offer appetizers, and you can usually order from the venue if you get hungry.
How do matches work? After each conversation, you privately note your interest on your Smart-Card, with selections due by midnight. Only mutual matches are ever shared, by email after the event. And if you don't match, here's what actually happens.
More questions? Our full FAQ covers the rest.
💛 One Last Cheeky Thought
Every story here comes from someone who showed up. They bought a ticket, walked into a room of strangers, and hoped something good would happen. Sometimes that hope comes out as a pamphlet. Sometimes it comes out as a strongly worded email the next morning. Nineteen years in, we wouldn't trade any of it.
We've got plenty more where these came from. Stay tuned for the next edition.
Curious what your own night would bring? MyCheekyDate runs host-led speed dating events across 65+ cities worldwide. No pamphlet required. Find your city at mycheekydate.com.
📊 A Note on These Stories
Stories were contributed by MyCheekyDate hosts from events across the company's 19 years. Guest names and identifying details have been left out. MyCheekyDate was founded in 2007 and has hosted 26,000+ verified events across 65+ cities in the last 10 years alone.