Guys help - is it a bad signs if a guy says “don’t be shy” to a girl ?

[Anonymous]

I like a guy in my class. He doesn’t know yet. We message mostly about school related stuff and he messages me right away ! When we were working in group project he was explaining me things and then he said “ don’t be shy”.. I told him I’m not shy then he said ok I’m going to let you win today.
Well I’m a quite girl and maybe appear as shy I’m not sure but I’m told a lot in my life that I’m quite! I call myself an “introvert” but not necessary shy!
Problem is that I like this guy and now I feel dumb to talk to him because he mentioned it to me 2x not to be shy or be confident!
Is it a sign he doesn’t like me? Or is it a sign that he is not really attracted to me? What do you guys think …

[Rob70]

I think he likes you. By telling you not to be shy he is wanting you to show if you are willing to share a more personal relationship. He is most likely afraid of being rejected if he just asked you out. If you like him talk about yourself a little more and maybe see if he would like to study yogether in person some time

[Clarke498]

It could be him just trying to get to know you

[Asker]

Probably !
Would you tell a girl you like not to be shy? Would you say that because she annoys you?

[Clarke498]

No, I'd say it to try to get her to open up. To feel safe

[Asker]

I have been messaging with the guy but it’s only me who I ask something , he does reply but he never messages me first. I try not to go too extreme and send many messages. Like 2-3 messages a day🥺 he replies the same.
Ugh I don’t think he is interested. Next weekend I will say ok to meet him to study for the test. Since he asked first.. I will see how it goes. But if he doesn’t initiate much than I guess I’m going to just forget about all this.

[Clarke498]

That's too bad, but yeah it's best not to force it

[kstout6]

He wants you to say something. I don't think its wrong.

[thearchjoker]

Its a saying it doesn't need to be taken literally the same way as you don't take "break a leg" or "whats up" in a literal sense. He wants you to express yourself thus saying "don't be shy" .

[Shy_Steve]

I could be wrong but I reckon he said that because he doesn't like your Shyness.

I don't think any Guy would mention it to you if they liked your Shyness.

[Itsdikshayo]

I liked a guy too and texted him miss you.. He texted back saying now take care and dont be shy..
I too am confused about what the dont be shy part meant..
What do you think?

[thearchjoker]

He likes you

[thearchjoker]

Not necessarily romantically, but he wants you to express yourself and hear from you more often