Is he shy or is my intuition wrong?

[Lillypond]

I have a guy friend who I talk to almost everyday online. Sometimes I initiate conversations, sometimes he does. I feel he has some kind of attachment after talking continuously for months because whenever I am online, if I don't initiate conversation, he would. He knows I am dating other guys. He never dated and he is kind of naive. He thinks it is wrong for me to be dating multiple people and says he steers clear of girls who are like me and who have close guy friends or have mostly guyfriends (which fits my description perfectly). Nevertheless, he continues to talk to me and during breaks, he would insist we hang out. But when we hang out, he feels the need to bring along another friend with him. I don't know what is up with him having to bring a babysitter with him. I mean, he is a grown man. Does his attachment means he secretly likes me and is just shy or is my intuition wrong? BTW, he likes to ask me lots of questions like "What are the signs that a girl like or doesn't like a guy?" or "What would you say if a guyfriend ask you out for dinner?"

[smackie9]

He could be feeling you out, playing with the idea of dating you. He maybe a grown man, but with the experience of a 12 year old. Dating this dude is going to be very confusing and frustrating. He is going to have issues with you having guy friends, will get jealous, and won't know how to handle himself. I dated someone like that and it was like dating a pouty little kid.

If you want to take your chances, you have to make some adjustments like putting more of your focus on him. Shy guys usually like a girl that is assertive and take the lead, so you are going to have to be a little more forward with him......good luck.

[bulrush]

Smackie got it right. He hasn't developed "dating skills" so dating him would be very confusing for you. He probably doesn't have real clear communication. But it does sound like he likes you, he just lacks experience. And with a shy guy like him, the girl really needs to take the lead, ask him out on dates, start kissing, etc, or things will go nowhere.

Are you ready for all these complications?