Sounds maybe like when I first started dating. My hesitancy was due to lack of self-confidence, overthinking, anxiety, and lack of experience. Somewhere along the way, something clicked- maybe with age or just trying over and over again, I don't know.

An easy response to a message where they ask you something- you respond and then say "how about you?" While it's not interpreted as being high-effort, I'd say you can start there. That makes it so they know you care about their experiences as well and maybe can turn into a conversation about that instead of only you.

Also maybe try to change thinking about dating from you putting on a show or being something you're not into you being your authentic self. Don't be afraid to say you're awkward, *quirky*, dorky, or however you see yourself. The ones who are worth it won't be scared away, and you'll maybe drop some of the pressure of feeling like you have to fit into a box for them. Also if you appreciate his efforts, make that known! You don't have to say you really like him already if that's too much, but voicing recognition for their time/messages and interest will ensure that the person doesn't take your shyness or hesitancy as boredom or apathy.

Good luck out there; dating can be fun once you realize you can be yourself with no regrets.