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"My biggest regret" — OkCupid question answers

"My biggest regret" — OkCupid answers that work

SecretsBy Bhupendra Singh Chauhan · Updated August 13, 2026

On this page
  1. 01How to answer
  2. 02Ready-to-copy answers
  3. 03Answers that work
  4. 04Answers that fall flat
  5. 05The strategy
  6. 06Common questions
  7. 07Related questions

How to answer "My biggest regret" on OkCupid

This question asks for something you have actually finished thinking about, not something that still hurts. The answers that work name a real regret and then show what came of it — a decision, a habit, a different way of doing things now. The most common failure is the no-regrets answer, which sounds wise and refuses the question at the same time.

136+ ready-to-copy "My biggest regret" answers

Tap any line to copy. Pick a strategy chip to filter by angle. Edit before pasting — verbatim copies read flatter.

absurd then true · 18

emotionally revealing · 13

escalating stakes · 19

low stakes confession · 14

playful misdirection · 16

sensory anchor · 18

specific detail · 19

tonal range · 19

Three "My biggest regret" answers that work

  • specific detail

    Not learning to swim until I was thirty-one. I spent a decade turning down boat trips and pretending I did not fancy it. Now I swim badly, twice a week, and enjoy it enormously.

    Why it works: A real regret with a specific age and a specific cost, then a resolution that is modest rather than triumphant. Swimming badly and enjoying it is far more likeable than having fixed the problem.

  • emotionally revealing

    I let a friendship go quiet because I was embarrassed about how long I had left it. Four years of silence over something one message would have fixed. I send the message now.

    Why it works: Names the mechanism rather than just the loss — embarrassment compounding into avoidance is something most readers recognise instantly. The last line turns a wound into a habit.

  • tonal range

    Studying the sensible subject instead of the one I actually liked. It worked out fine, which is somehow the annoying part. I still read about it constantly and my flat is full of the books.

    Why it works: Admitting it worked out fine keeps the answer honest instead of dramatic. The books at the end are a concrete thing the reader can ask about.

Three that fall flat

  • no regrets refusal

    No regrets. Everything that happened made me who I am today.

    Why it falls flat: One of the most common answers to this question, and it is a refusal dressed as wisdom. It fills the space without telling the reader a single true thing about the person writing it.

  • blame shifting

    Staying with my ex for two years after I knew it was over. She was manipulative and I was too soft to leave.

    Why it falls flat: The regret is real, but naming a partner and her faults moves the story onto someone who cannot reply. The reader quietly wonders how they would be described in two years.

  • trivial answer

    Not buying that jacket in Berlin. I still think about it.

    Why it falls flat: Charming for a second, then empty. The question offers room for something real and this politely declines it, so the reader finishes knowing what they already knew.

Pick something you have finished thinking about. A regret that has arrived somewhere reads as self-knowledge; one still open asks the reader to help carry it, which is a lot to request before a first message. Keep it yours — the moment a name enters, the reader starts wondering how they will be described later. Small and specific beats large and vague, because a real regret has a date and a place attached. And avoid the no-regrets line: it is the most common answer here, and it declines the question while sounding like an answer.

Common questions

What should I write for "My biggest regret" on OkCupid?

Something you have finished thinking about, with the outcome attached. A regret that arrived somewhere reads as self-knowledge, while one still open asks a stranger to help carry it before you have exchanged a message.

Is "I have no regrets" a bad answer?

It is one of the most common answers here and it refuses to answer. It sounds like wisdom but tells the reader nothing, so they finish the line knowing exactly what they knew before reading it.

Can I mention an ex in this answer?

Better not to. Naming a partner and their faults moves the story onto someone who cannot reply, and readers tend to imagine themselves being described the same way once things eventually end.

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