“What a shame” expresses disappointment, sympathy, or regret about an unfortunate situation. The best alternative depends on how serious the situation is: “that’s too bad” is casual, “that’s unfortunate” is neutral, and “I’m sorry to hear that” is more personal.
Match the Phrase to the Situation
- That’s too bad
- That’s unfortunate
- That’s a pity
- What a pity
- How disappointing
- That’s disappointing
- What a disappointment
- What a bummer
- That’s a real shame
- I’m sorry to hear that
- What a loss
- How regrettable
That’s too bad
A common, informal response to disappointing news or a minor setback.
Example: That’s too bad—you were really looking forward to the concert.
That’s unfortunate
A neutral choice that works well in professional or restrained contexts.
Example: That’s unfortunate, but we can reschedule the appointment.
That’s a pity
A close alternative that sounds natural in British English and in mildly formal conversation.
Example: That’s a pity; I would have liked to see the exhibition.
What a pity
Expresses regret in much the same way as “what a shame,” often with a slightly traditional tone.
Example: What a pity that the weather spoiled the event.
How disappointing
Focuses directly on the letdown rather than sympathy for the person.
Example: How disappointing after all the work you put into the application.
That’s disappointing
Straightforward and useful when the result itself failed to meet expectations.
Example: That’s disappointing; the new feature still has the same problem.
What a disappointment
Stronger than “that’s disappointing” and suited to a notably poor outcome.
Example: What a disappointment—the performance was nothing like the reviews suggested.
What a bummer
Very informal and best for everyday setbacks among friends or familiar colleagues.
Example: What a bummer that your flight was cancelled.
That’s a real shame
Adds emphasis while keeping the original expression natural and sympathetic.
Example: That’s a real shame; she would have been perfect for the role.
I’m sorry to hear that
A warmer response when someone has personally experienced bad or upsetting news.
Example: I’m sorry to hear that your plans fell through.
What a loss
Best when something valuable, promising, or important has genuinely been lost.
Example: What a loss for the team—he contributed so much.
How regrettable
Formal and relatively uncommon in conversation, but suitable for serious written commentary.
Example: How regrettable that the agreement collapsed after months of negotiation.
Avoid Sounding Dismissive
Short phrases such as “that’s too bad” can sound sympathetic or dismissive depending on tone and context. For serious personal news, a fuller response such as “I’m sorry to hear that” is usually kinder.
“What a loss” is not a general replacement for every disappointment; reserve it for situations involving a meaningful loss.