Crushing It In Cougar Town

(I am a software engineer. I’ve just accepted a contract for work in my hometown and am traveling back for the first time in a decade. I don’t use social media so no one there really knows what I’ve been up to unless I was close to them. While doing basic research for the contract while on my flight, the client’s name sounds familiar, and basic snooping reveals she’s the mother of a former classmate. Thinking I can have a chuckle with the client later, I brush it aside and don’t even notice a familiar face checking me into the hotel later.)

Former Classmate: “Okay, so I have a room for [My Name]… Wait. Are you [My Name] that went to [School]?”

Me: “Huh? Oh, s***! [Former Classmate]?! Oh, h*** no… Someone has to be pranking me right now.”

Former Classmate: “Well, that’s not what I’d expect after not seeing me since high school!”

Me: “Sorry. You’re just the last person I expected to run into randomly while I was in town for work. I didn’t even know you got into the hotel business.”

Former Classmate: “That’s fair enough. What are you doing for work, then?”

Me: “Oh, this and that. I go wherever they send me and do what I need to do really.”

(We talk for a good half hour, catching up on what’s been happening in town and what mutual friends are up to.)

Former Classmate: “I hope you enjoy your time back in town! Maybe we can grab dinner and get a bunch of us back together!”

Me: “Sounds fun! Hope it doesn’t get weird, though. I’m in town to see your mom! Ha!”

(I walk away while she gives me a look of horror. I think nothing of it, but she seems to avoid me for the entire time I’m there. A few days before I leave, her mom takes me out to a fancy dinner for my work — a common thing — and brings me back to the hotel. When she learns where I’m staying, she tells me about her daughter. I tell her I’m a former classmate, and she decides to come in and have a laugh with her daughter about it.)

Former Classmate: *seeing us walk in* “OH, GOD, MOM! PLEASE, NOT WHERE I WORK!”

Client: “What? I just wanted to say hi and bring [My Name] back to his hotel.”

Former Classmate: “DO YOU HAVE TO F*** EVERY GUY I’M ATTRACTED TO?!”

Me: “Whoa! Wait, what?!”

Client: “IS THIS THE CLASSMATE YOU HAD A CRUSH ON ALL THOSE YEARS?!”

Me: “WHAT?!”

([Former Classmate] ran to the back crying. Turns out, my client was a cougar and she and her daughter had very similar taste in men. When I told her I was here to “see your mom,” she thought I was a male prostitute and couldn’t bring herself to look at me. After her manager brought her back out, I showed her my business card to prove I was NOT sleeping with her mom.)