This research examines the effects of pre-counterfactual thinking and anticipated emotions on the amount of the first bid placed in Name-Your-Own-Price auctions. The results of Study 1 indicate that upward counterfactuals are elicited more than downward counterfactuals in response to both accepted and rejected bids. Study 2 investigates the effect of imagination of upward counterfactual thinking on the first bid. The results indicate that upward pre-counterfactual thinking about an accepted bid results in anticipated regret, which increases the amount of the first bid; however, the amount is not influenced by anticipated disappointment resulting from pre-counterfactual thinking of a rejected bid.