Example: I had a financially irresponsible acquaintance who owned by far the nicest pool table I’d ever played on.
It was already a fine, expensive table when it was built a century ago. Now it had become a valuable antique. Impeccably maintained. Just perfect. If a ball didn’t go where you wanted it to go on that table, that was on you, because it was flawless.
To make a long story short... At one point the acquaintance offered this stunning table to me at a below-market price. However, it was still more than I was ready to pay cash for at that moment. Not wanting to offend him, I didn’t make a counteroffer. I did say, however, that I was very interested. He should be able to get his asking price, but if it didn't sell fast at that level, please put me at the top of his list to make a deal.
I inquired again about the table a while later, and was stunned to find out that he had impulsively made a deal too sell it for about 1/5th of the price he had offered me, and an even smaller fraction of its actual value.
The table was still on the third floor of his house, waiting to be moved (at a cost which must have exceeded the rock-bottom price). When I asked why he hadn’t called, he said, “Oh, I needed the cash and didn’t think you were really that interested.” (Note: Same guy recklessly sold a beautiful vintage car far below market price, when he knew a friend was salivating to buy it, and surely would have paid the same or more. Like I said... Financially irresponsible.)
OK, fine, whatever. I missed out. My missed opportunity.
Now, what if I had said: “Listen, your buyer hasn’t moved the table yet... How about canceling the sale and I’ll give you $1,000 more for it.” That still would have been a fabulous deal for me. And the seller probably could have used the extra cash. But it would have been a really squirrelly thing for both me and the seller to do.
I let it go. Live and learn. Next time, I’ll make a counteroffer on the spot. But I wouldn’t try to go around a made deal even when it was advantageous to both buyer and seller.