Mine are: a rejected offer or canceled escrow ( usually, but not always).

In this seller's market and shortage of the housing inventory, I feel the pain of the first time buyers..... They are very sensitive and it is really difficult to tell them that their offer is rejected.

Sorry but your did not get the house. I hate that Jeff.

They took the other offer. 

Bad news may create some stress for all of the parties including the agent. Make the difficult calls first as a regular policy.

Good morning Jeff. I handle the most difficult calls first thing in the morning, not matter what the issue is. I want then off my plate, as quickly as possible.

Make it a great week!

there's a laundry list of unpleasant phone calls that every listing agent needs to make....the important factor is to not make it personal....it's business and we are often the bearers of bad news....

The one where a client either reasonably or unreasonably is upset over something that I can't fix.

The ones where I had to disappoint. Sometimes I would wait a day.

"When I stopped by Friday to check all it well at your house, when I entered the carpet was wet...The main water source has been shut off.....the inlet to the master bath toilet grommet failed...I've contacted....who is able to come out today.....I need you to call them to authorize service......the cost will be covered by the homeowners insurance that covers the seller also."

The toughest ones are when you really need a client to reduce the asking price and/or when the inspection results news is not so good.

I find it difficult to tell buyers that someone else outbid them.

Telling a buyer they did not get the house......

I would agree with Noah that letting a buyer know they did not win the bid is the hardest call and next to that to let a Seller know that the buyer did not accept their offer.

Jeff - You and Noah basically stole my answer. I take it personally when I have to let someone know they missed out on a home; either because the seller did not accept their offer, or because it went pending just before we were able to make an offer.

Letting the seller know that the showing did not lead to interest is much more difficult because the seller's options are more limited than the buyer's.  I dread making that call.  I usually make that call about midday ... do not want to either open or close the seller's day on a sour note.

Hi Jeff

Fortunately we are able to deliver some great news a lot of the time.  

And then there are those calls:

I'm sorry the buyer is canceling the transaction

The buyer is having loan trouble.

The appraisal is a problem.

You didn't get the house.

The buyer(or seller) is not responding to your offer(or counter offer).

The rabbit died.

Deal with it as soon as possible. Life happens. We can mourn but just for a minute.   We move on.

The hardest calls to make are the 'bad news' calls - 1) The seller chose another offer 2) the buyer cancelled the deal 3) The buyer wants a ridiculous 30 item repair list done..

you get the picture!

the buyers inspection notice it just pains me when buyers come back with a list of 40 50 60 items to be repaired it seems like they didn't even see the house before they made the offer, then the buyer's agent tries to insist that these are all items that are going to be required by the lender to be repaired its just frustrating. my problem is I don't want my sellers to be responsible for any of the repairs because then I'm afraid that if they're not done right the buyers going to come back and try to sue them after the close because of some problem

I agree with a lot of the answers here but I personally don't like sharing showing feedback that's negative. Especially if it's something out of the homeowner's control (like bad neighbors). 

I agree with Michael Thornton.  Conflict resolution is tough.  Especially home inspection items.  Buyers want items repaired, and sellers don't want to fix them.  Or sellers fix the items, but the fix is examined by the buyers at pre-settlement walkthrough, and the fix is not what the buyer had in mind.  Just one example.

I would have to say, :sorry, your offer was not accepted"

Jeff Dowler CRS: Noah Seidenberg got it right.

When a client is holding an extreme position with a closed mind.

When te buyers decide to walk away from a contract.... I hate breaking the bad news to the excited sellers :-(

 Conflict resolution is the hardest. Occasionally, people find something during remodeling that was not visible during the inspection. It is hard to overcome the situation when the contractor says, "the inspector should have seen that."

Rejections.

Great question

1- to let the seller know the property appraised for less than we are trying to sell

2- to tell the seller that the buyer wants more repairs because of appraisal

3-to let buyer know seller will not do any more repairs

4 to let buyer know seller is unwilling to lower price due to appraisal

5- to let seller or buyer that the other party wants to cancel deal

hope you have a great month Jeff Dowler