This is the number one mistake I see really smart people make every single day.
It feels like the more pain you're in, the more aggressive stretch you need to do, but it's exactly the opposite.
The more pain you're in, the more gently you need to stretch because the pain you feel in your body sets your body on high alert. Your body will do anything it can to protect itself from further injury.
If you're already in pain and you push into a stretch too far causing more pain, your body thinks it's getting injured and it locks down even tighter. You can truly make yourself tighter instead of loser by doing a stretch too aggressively.
This one shift in perspective is a game-changer. If you can be really gentle with your stretches when you're in a lot of pain you will get better so much faster.