You might consider a table that basically is one row per interaction.

You'd have the seller's account ID, the interested party's account ID, 
the ID of the item in question. A field with an "interaction type" value 
- different codes for what's going on. Maybe a currency field for the 
value in question - i.e. the price if buying outright, or an offer price 
if the buyer is trying to haggle, and then the seller's counter offer 
price should he respond.

So something like:

TTransaction
TransactionID (int identity PK)
ItemID (int FK on item table)
SellerUserID (int FK on user table)
BuyerUserID (int FK on user table)
CurrentPrice (currency/money data type)
InteractionType (could be int with FK to a table with the various 
interaction types listed, or just a simple code with no extra table)
Timestamp (date/time, autopopulated)

You could then pull all the appropriate records at any time and list out 
the history of the transaction.

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