Anyone else feel weirdly guilty about being socially behind?

I’m a 24 year old guy, and this has been bothering me more than I expected.

On a recent work trip, a woman I work with said something that’s been stuck in my head. We were in the hotel elevator after a long day in the office and a work offsite, and right before she got off she said, “If you’re doing anything for dinner let me know and I’ll join you.” In the moment, I didn’t think much of it. I just wanted to order food and be alone, and since we’re on the same team with the same manager, I played it safe. Looking back, I realize I liked talking to her that day and probably should have made more of an effort instead of being passive. About an hour later I texted her saying I had accidentally fallen asleep and asked for food recommendations and she gave me some, and that was it.

Nothing dramatic happened, but I’ve been stuck feeling like I missed something again.

This isn’t the first time. Last year on another work trip, a colleague suggested dinner, we went, and she texted me for weeks before suddenly ghosting me. Even then, I was never sure if she was interested or just being friendly. Before that, when I was 22, a woman at a bar flirted pretty clearly and I completely froze.

What’s bothering me is the feeling that I’m behind for my age. It seems like most people around 24 are already comfortable picking up cues and taking chances, while I hesitate and overthink. I can’t tell if I’m actually behind, or if this is more common than it looks at my age and people just don’t talk about it.

If anyone relates, I’d honestly like to hear it.

Is this normal, or is there something off about me?