Regret is a tricky thing. It creeps up quietly - sometimes years later - after we’ve moved on, healed, or convinced ourselves that everything happened for a reason. But when it comes to dating, regret often lingers a little longer. Maybe it’s because relationships expose the most vulnerable parts of us. Or maybe it’s because the “what ifs” in love hit harder than in any other part of life.

So, what’s your biggest dating regret?

For some, it’s the one who got away - the person you pushed aside because you weren’t ready, only to realize later they were exactly what you needed. For others, it’s the one you stayed with too long, ignoring every red flag because you didn’t want to start over again. And for many, it’s not choosing yourself - compromising who you were just to keep someone who didn’t deserve you.

The Regret of Silence

A common one? Not saying what needed to be said.

We often replay those moments in our heads - the text we never sent, the apology we held back, the feelings we hid out of fear of rejection. Sometimes, we’d rather protect our pride than risk the pain of being honest. But silence can be its own kind of heartbreak.

The Regret of Settling

Then there’s settling. It doesn’t always look like lowering your standards - sometimes it’s subtler than that. It’s staying because it’s comfortable, because “they’re nice,” or because everyone around you is pairing off and you don’t want to be left behind. But deep down, you know that comfort isn’t the same as connection.

Settling might keep you safe, but it rarely makes you happy.

The Regret of Not Loving Enough - or Loving Too Much

Some people regret not giving love a real chance. Others regret giving too much of themselves away. There’s a delicate balance between protecting your heart and opening it fully, and most of us only learn it the hard way. We look back and wish we’d either built better boundaries - or torn them down sooner.

Learning to Let Regret Teach You

The truth is, everyone has a dating regret. But those regrets, painful as they are, shape the way we love next time. They make us wiser, kinder, and more honest - not only with others but with ourselves.

So maybe the question isn’t “What’s your biggest dating regret?”

Maybe it’s “What did that regret teach you?”

Because at the end of the day, the only real regret is not learning from it.