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I've seen many great watches, but for the finest watch I ever saw at random in the wild, read this repost of something I wrote over two years ago:
So I'm sitting at Starbucks in Framingham, Massachusetts, twenty miles west of Boston, with my 3-3/4 year old son to get a snack. He hasn't napped so he's just hanging on to serenity by a thread. Sitting next to me is a gentleman, casually dressed in very fine clothing, sporting an asymmetric watch in a white metal. Hmmmm. I can't help but stare. You know what question I'd like to ask, but the man is talking with a female companion and I don't want to be rude, so I bite my tounge.
Ah, serendipity....they make like they are going to arm wrestle and the woman asks me to count to three. I oblige. The woman tries to win and the man makes like he's in casual conversation with me, showing he is not feeling any exertion. I play along, "Please tell me about your watch," I say.
"It is a Patek Philippe." He takes it off and allows me to handle it. It is gorgeous. I reciprocate and hand him my VC Jubile 1755. It is not a fair trade, but the least I could do. He tells me that I'm only the second person to take notice of his watch. It's hard having a proper conversation with him, since my son keeps interrupting. I hand the watch back to him with thanks. Preventing the thread of serenity from being cut in a public space trumps WISdom. 
Folks, it was a 3424 in platinum. They don't make them like they used to and they hardly made them then. This is the best picture I could find on the net, though it is of a white gold model (from Antiquorum).

I love that turn of phrase, Bill. Do you mind if I use it?
Some of us around here perhaps hang onto sanity by a thread, too!
Nice story. I have nothing to match it but my only true 'in the wild' encounters have been a steel mid-1960's Omega Constellation on an elderly gentlemans wrist in one of our cities best coffee joints and a diamond encrusted Frank Muller in a large Cintree Curvex case in a nice restaurant in Singapore. The wearer was being flashy and loud in other ways too and I didn't feel comfortable engaging him in conversation about the watch.
There have been other nice watches on wrists of shoppers in watch boutiques, but I kind of rule those out from true, random, in the wild sightings.
Andrew
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... a guy I was seated next to at a work-related dinner. And I was wearing a Journe too!! For both of us the only time that happened "in the wild"
Andreas
Does this count?
It happened in the tiny old ABP store a few years ago. Given that it is a watch strap atelier, you would expect that visitors might own or wear some decent hardware. As we were discussing the finer points of electric orange toadskin straps for a Panerai, a dashing English gentleman came into the store. It was enough that he was wearing a complicated Patek (no, sorry, no idea which: it was not a place to be staring intently!). However, he then produced a stylish leather watch-carrying case and from within that case he removed a watch carefully wrapped in a dustcloth and explained to the proprietor of the boutique that he wished to have a strap made for the watch in a colour similar to that of the case. That watch, even from a furtive glance at five paces, was dazzling for its elegance, presence and finesse. It was [then] not a familiar piece, but upon being unwrapped it 'filled' the entire boutique. Have you experienced such an effect?
The boutique owner handled the watch appreciatively and asked who the maker was. The Englshman replied with a name that sounded like 'Limousine', but it was indistinct. A subsequent retelling of the story and a 'callout' on this forum failed to produce any insight as to what that watch might have been, but it was possible to know instinctively that it was very special. The identity of that piece has remained a vexing mystery, and the failure to overcome reserve and engage the gentleman in conversation has remained an eternal regret. Any insights, even now, would be most welcome.
Cheers,
pplater.