You got matched with your friend’s single dad. What could possibly be wrong?
Cole is a 55-year-old divorced businessman. He is new to online dating and was persuaded by his friends David and Jennifer to create a profile. He is initially reluctant but ends up matching with Yomi, his child's friend. He has gray in his beard and is described as looking 'expensive' in a tuxedo. He is active, as shown by a hiking photo from Aspen.
The Profile Creation (Two Weeks Earlier)
Cole Bennett sat in his home office, nursing a whiskey while his two closest friends commandeered his phone like it was a hostage situation.
David: Cole, you can’t use the photo from Alex’s graduation. You’re wearing a dad polo.
David said, scrolling through his camera roll with the determination of a man on a mission.
What’s wrong with polos?
Cole protested weakly.
Jennifer: Nothing, if you want to attract other dads. We’re looking for ‘distinguished bachelor,’ not ‘will help you move furniture.’
Jennifer chimed in from her perch on his desk.
Cole sighed, swirling the amber liquid in his glass. Three years divorced, and somehow he’d let these two talk him into this. Online dating. At fifty-five. He’d rather negotiate with hostile investors.
David: Oh, this one! From the Thompson Foundation gala. You look like James Bond’s more successful older brother.
David held up the phone triumphantly.
I look uncomfortable in a tuxedo.
Jennifer: You look *
expensive
* in a tuxedo. There’s a difference. Yes. That one. Also this hiking one from Aspen—shows you’re active. And…fuckable… this one from the office where you’re laughing. Candid. Approachable.
Jennifer leaned over to examine the photo.
I hate this.
Cole muttered, but he was smiling slightly.
David: Bio time! Keep it simple. Honest.
David announced, opening the Tinder app they’d already downloaded.
After twenty minutes of debate and three more whiskeys, they settled on:
“New to this. Friends insisted I try. Love good conversation, great food, and terrible puns. Let’s grab coffee?”
Jennifer: The pun thing is good. Self-deprecating but confident.
Jennifer nodded approvingly.
Can we be done now?
Cole reached for his phone.
David: One more thing. Age range. What are we thinking?
David held it away.
I don’t know. Forty to fifty-five?
Jennifer: Forty to fifty. Keep it reasonable.
Jennifer said, already typing.
David: And radius… let’s say twenty miles.
David added, handing back the phone.
What Cole didn’t see was Jennifer’s last-second edit as she grabbed the phone back for “one final check”—her fingers quickly changing the range to 20-50 with a mischievous glance at David.
Jennifer: All set.
She said innocently, returning it to Cole.
David: There. Done. You’re live. Welcome to modern dating, old man.
David handed back the phone with a grin.
Cole stared at the profile—his own face smiling back at him from the screen. When had he gotten so much gray in his beard?
I’m going to get zero matches and you two are going to owe me dinner.
David: Twenty bucks says you get fifty matches in a week.
You’re on.
He got seventy-three.
-----
The Match (Present Day)
Cole was in a board meeting when his phone buzzed. Then buzzed again. And again.
He ignored it—years of discipline kept him focused on the quarterly projections being presented. But during the break, he checked his notifications and felt his stomach flip.
IT’S A MATCH!
The profile showed someone young, attractive, with beautiful eyes hiding most of their face underneath fishnet fabric in their photos. Cole stared at the screen, his thumb hovering uncertainly. He should wait. Play it cool. That’s what David would say.
He typed anyway:
“Well, this is unexpected. In the best way. I’ll be honest—I’m new to all this and slightly terrified. But you seem worth the terror. Coffee this week?”
Send.
Immediate regret. Too eager? Too honest? Too—
Buzz.
His heart rate picked up as he read the response, and before he could overthink it, he suggested:
“Thursday? There’s a great place called Roast on Fifth Street. 11am?”
When the acceptance came through, Cole found himself smiling at his phone like a teenager.
Jennifer was going to be insufferably smug about this.
-----
The Meet (Thursday, 10:58am)
Cole arrived eight minutes early—a habit from decades of business meetings—and immediately regretted it. He’d changed his shirt three times that morning. Three times. Like a teenager.
He chose a table with a view of the door, ordered a black coffee to occupy his hands, and tried not to check his phone every thirty seconds. The café was busy with the late-morning crowd, the scent of espresso and fresh pastries filling the air.
At 10:59, the door opened.
Cole looked up with a welcoming smile that froze on his face.
No.No, no, no.
Yomi stopped three steps into the café, eyes widening in what could only be recognition. Now that he can see the face clearly and not from his phone screen. Damn it, he should have connect the dots!
For a suspended moment, they just stared at each other across the crowded room. Cole’s brain was short-circuiting, running through calculations: This was Yomi. Alex’s friend. Alex’s
friend
. The one who came over for movie nights and had eaten at his dinner table dozens of times. The one who’d helped Alex move into their apartment last spring.
The café sounds faded to white noise. Someone’s phone rang. The espresso machine hissed. Neither of them moved.
Cole stood slowly, his business-negotiation instincts kicking in even as his personal life imploded. This was a disaster. An absolute disaster. How had this even—the age range. It must have gone wider than he thought. Or—
God, had he actually checked what Jennifer and David set it to?
Yomi.
He said quietly, his voice steady despite the chaos in his chest.
I think under the circumstances, Cole is fine.
Cole said with a careful smile.
They stood there, the small café table between them like a demilitarized zone.
I guess it’s mortifying to you? Unexpected? Possibly the most awkward thing that’s happened to either of us this year?
We’re already here. And I did promise you coffee. Unless you’d rather pretend this never happened. I would completely understand.
He said, keeping his tone carefully neutral.