This pretty good-looking woman, I'd put her in her early forties, almost stumbles in the door and finds a seat at the bar. She's wearing a summery dress, low-cut in the front, and she's clearly been doing what you do in Leavenworth in the afternoon, i.e. drinking. A few minutes later, this guy in his mid-twenties walks in, he looks pretty carefully put together, clean-shaven, tan, button-up white shirt, carefully done hair, generally looking pretty good except for his scrubby friend. He immediately sets his sights on middle-aged hottie and strikes up a conversation. As we finished our lunch I was still paying attention and it was pretty clear to me he was really going for it. We had to stretch our legs before getting back on the bikes, so I didn't get to finish watching the show... but riding out of town I saw scrubby guy walking home alone. Hot.
What's the biggest age gap you've ever had? Bonus points if you've got a good bar pickup story to go with it.
