To Be Cringe Is To Be Free: Why the Best Dating Advice Is the Advice You Don’t Want to Hear

There’s a version of dating advice everyone loves to share: be patient, the right person will find you, trust the timing. They found love in their way and want to give you that gift. 

Well I’m not here to give you that advice today.

Here’s the advice you don’t want to hear: you need to go up to people. You need to stop waiting.

• Cringe Is a Skill, Not a Flaw
• Dating Has Changed .. But Control Hasn’t Moved
• What “Going for It” Actually Looks Like
• The Foundation Underneath All of This: Unconditional Self-Esteem
• The Real Advice, One More Time

Cringe Is a Skill, Not a Flaw

Somewhere along the way, we decided that “cringe” was the worst thing you could be. So we optimized ourselves out of it. We perfected the cool, detached response. We make AI our safe space. We waited for the algorithm, the app, the “sign,” the perfect opening line – anything that let us avoid the one thing that actually works: walking up to another human being and saying something, even if it’s a little awkward. But here’s the truth nobody markets to you: cringe is what freedom looks like from the outside.

The people willing to be a little cringe – to wave first, to ask the question, to say “I thought you were interesting and I wanted to say hi” –  are the ones actually living their dating life instead of narrating it from the sidelines. Cringe isn’t a character flaw. It’s a rep you took that most people were too scared to take.

This is my extrovert propaganda, and I’m not sorry about it: go be a little cringe. On purpose. Today.

Dating Has Changed .. But Control Hasn’t Moved

Yes, dating has changed. This is especially true when I am talking to folks who are divorced or widowed – who have only had 1 big love. Now – the apps, algorithms, situationships, the slow fade –  the landscape is different than it was ten or twenty years ago, and I’m not going to pretend otherwise. But here’s what hasn’t changed: you are still the one who gets to take control of your own dating life.

Waiting for the “right” match to land in your inbox is not a strategy. It’s a delay tactic dressed up as patience. The people who actually move forward …who actually meet someone…are the ones willing to close the laptop, walk into the room, and go for it.

What “Going for It” Actually Looks Like

I met with someone recently who was widowed. They’d moved through the loss – really moved through it, done the work, sat with it  and now they were standing at the edge of something new, trying to figure out what “what’s next” even looks like. That’s not a small thing. Starting over after loss, after divorce, after a long stretch of not dating at all – it takes a specific kind of courage that has nothing to do with being smooth or confident on paper. It has everything to do with being willing to feel a little cringe, a little exposed, and doing the thing anyway. That’s the through-line for almost everyone I work with, no matter what stage of life they’re starting from: the willingness to be seen trying is the whole game.

The Foundation Underneath All of This: Unconditional Self-Esteem

None of this – the approaching, the awkward opener, the willingness to be a little cringe in public – works if your self-worth is riding on the outcome. If every approach is secretly a referendum on whether you’re lovable, of course you’ll avoid it. Who wouldn’t?

The real unlock is what some call unconditional self-esteem – a sense of your own worth that isn’t contingent on whether the person says yes, whether the date goes well, or whether you get the outcome you wanted. When your self-esteem doesn’t depend on the response you get, “going for it” stops being a gamble and starts being just… something you do. I recently came across a great piece on this exact idea — worth a read if this concept is new to you.

The Real Advice, One More Time

Stop waiting for the sign. Stop waiting for the algorithm. Stop waiting to feel ready, because “ready” is a feeling that shows up after you’ve already started, not before.

Go be cringe. Go say hi first. Go text them back too enthusiastically. Go approach the person at the coffee shop, the wedding, the dog park, the industry event.

Cringe is not the opposite of cool. Cringe is what freedom looks like when you stop performing and start living.

Ready to stop waiting and start dating with intention? Reach out to Michal Matches and let’s talk about what’s next.