“Hey man, I’ve got to tell you a story,” says the guy at the bar as I bring him back his credit card after closing his tab. He’s in his early thirties, dressed professionally, and pretty talkative after downing two Johnny Walker Blacks and a tall soda. It’s a busy night, but everyone has been taken care of for the moment so I lean in to hear what he has to say.

“I’m in the city for a convention. There’s was a big dinner for everyone tonight downtown, but it was really expensive so I couldn’t afford to go. Instead I got on the bus going to the dinner and figured I’d try to sneak in without a ticket.”

“Did you get in?”

“Well, on the way there I ended up sitting next to this lady who’s the president of a national professional association in my industry. We talked the entire ride over. She’s a good person to know. Great luck, right?”

“Indeed.”

“Yeah, but when we got to the dinner I couldn’t get in.”

“That’s embarrassing.”

“Yes, but she gave me her number and her hotel room. She wants me to come over later tonight and, you know, take care of her.”

“Oh, wow. No kidding.”

“And she could really advance my career.”

“So are you going?”

“Well, there’s just one problem. She’s 82.”

“I see…”

“I’ve been drinking all night trying to get up the nerve to go see her, but I just can’t do it! She’s already called me once to see where I am. I need your advice. You’re a bartender, you should know what to do in this situation. I used to be a bartender and people came to me all the time.” He’s getting ready to write the tip onto the credit card slip when he pauses. “Your tip depends on this, so you better give me some good advice!”

With money and further entertainment from this guy on the line, I dive right in. “OK, here’s what I would do. Stay out and keep having fun. Then when it’s really late, say one or two in the morning, go up to her room and knock very lightly on the door.” I pantomime an extremely light knock. “She’s old, she’ll be asleep. Sneak away. Then, in the morning, send her an email saying you came by but she must have been asleep. Say you’d like to stay in touch anyway.”

I think this is a good strategy, but he doesn’t seem impressed. “I don’t know man. Maybe I should go up there. I already asked my girlfriend about it.”

“You asked your girlfriend?” I’m really thinking, “You have a girlfriend?!” Of course I don’t say that.

“Yeah, she hung up on me! Said I was an asshole. Can you believe that?”

“I can believe that.”

“I mean, this woman’s 82, why should she care.”

“Not exactly competition…”

“Exactly. So should I go up there? This woman could do so much for my career.”

“It’s a tough call.” I don’t really think it’s a tough call at all, but he does, so I go along with it.

“I think I’d need to drink some more, but if I do I’m afraid I’d throw up on her!”

“That probably wouldn’t be good for your career.”

“No. But she looks pretty good. For 82, you know.”

“Yeah. Well, I told you what I think you should do.”

“Yeah, thanks. I’ll think about it. Have a good night.”

“You too, buddy.”

He walks off and waves goodbye. I open the bill to find a six dollar tip. For two drinks and advice on how not to sleep with an 82 year old woman, I think that’s pretty good.