“Sterling” is good; you can use it as the first part of his name and add other thoughts to it.
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I not so long ago had a “Sterling”, so that’s not an option for this guy 
I’m not particularly a fan of grays, but this dude is pretty striking so I’m willing to be won over. Another suggestion I got was Clean Slate, going along with the starting over theme.
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First name that came to me with his photo was Darcy or Mr. Darcy, from Pride and Prejudice.
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How about Coin Toss?
Instead of silver, what about steel related?
Stainless Of course, once he goes white, maybe more ironic than accurate…sorry
Damascus (yeah, I know there was one, but…)
Forged (in) Steel
Forge On
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Or Remington, Remy around the barn.
Remington Steele 
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I had that thought, too. So many episode titles could work, too… 
that show
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Since this will be the special horse to turn your luck around, how about: Talisman?
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Grayson.
My gray was Bob. I don’t do color related names.
Well he’s fancy! Here are some fancy names 
Fiat Lux - “let there be light”
Exchequer - a royal or national treasury.
My Lord Scamperdale - “No man rides harder than my Lord Scamperdale - always goes as if he had a spare neck in his pocket.” - Robert Smith Surtees (1860). “Mr. Sponge’s Sporting Tour”
Le Sabrage - a technique for opening a champagne bottle with a saber, used for ceremonial occasions.
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Oh he is stunning. I’m sorry to read of all your awful bad luck. Count me in as another that is not usually a fan of greys, but his expression and eye won me over…
Not very good with name suggestions. I once very originally named my silver point Siamese Silver. He was a great cat that deserved better. No other cat has come close to him, though I’ve had many.
Keepsake? Trying to think of names that tie in your history and his. Slate?
How about Moonstone? (Stony for a barn name).
Or Jasper?
Or Picasso? (I’m thinking that there’s kind of a cubist quality to the dapples on the coat). Barn name Pablo.
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He is absolutely stunning! Since Sterling is out, I really like the Unexpected name. Sounds classy and fits your situation!!
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I like rock names.
The name is in the title of your post - Starting Over.
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He’s here! And he’s, ummmm, MUCH bigger than I expected 
After meeting him, I decided to go with “Stylish”, Styles for short, although I’ve also been calling him Snorty McSnortyface since he has a funny way of blowing out of his nostrils in new situations.
I haven’t actually ridden him yet as it’s been over a year since anyone has been on him and I’m going to essentially start him over like he’s a three-year-old. So far he is lunging well and quietly in both directions wearing tack and starting to stretch down on his own. Next week when I have a ground person I’ll jump on and see where we are. Despite the fact that for the past couple years he’s been living out and feral (seller’s description!) he has been very polite to handle and is adjusting to being back in a stall half the time.
Did I mention he’s enormous? When I asked, the seller told me he was “oh, maybe 16.1” but he’s a very solid 16.3 with no shoes and huge bone. I’m 5’4” on a tall day so I’ve asked Santa Claus for a bigger mounting block. 
Thanks for all the suggestions and wish us luck!
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He is lovely! Congratulations!
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He is so pretttttty!!!
I love Stylish.
I am sure Snorty McSnortyface will settle in quickly.
keep us posted!
