[Flowerpower7]

Say you are a 30 something shy-guy, who lets the girl always make the first move as you lack some self confidence. You are quiet, never talk about yourself and never ask questions about others. You also dont have any female close friends because you believe that the woman you date is your ONLY friend.

You are trying to seek an outgoing, popular girl to date, but its just not working out for obvious reasons. You havent dated anyone in over 2 years.

There is a girl who is interested in a relationship with you, but she is not outgoing like the girls you want. You have told her in the past (2 years ago) that you arent interested in her.

Would you, tease and joke around with this girl...knowing you dont want her??

REMEMBER: He is not MOST guys. He is SHY.

SHY people have very different behaviours than "normal" people

[Siciliana]

Remember, people have an uncanny ability to flirt with and have sex with people they don't want to be with becuase they have nothing better going on, they are bored, they are horny... whatever the reason, they do it.

The best way to judge what people say is believe 50% of what you want to hear and 150% of what you don't want to hear him say. If he told you 2 years ago he isn't interested, I am sure that has not changed. If he told you that would consider dating you now, I would take that as, "I have nothing else going on".

People generally don't grow attracted to someone they have already put in the Friend-Zone.

[Mike B.]

Sure. If a shy person feels comfortable around you and views you as "non-threatening," then they can tease and joke around with you just like anyone else, especially if they know that you like them. That can make them potentially feel even more comfortable around you.


Wondering if you are getting signs? I wouldn't read too much into it. I think if he really likes you or whoever is in this situation, it will become obvious if they like you in that way even if they are shy. Being shy doesn't necessarily mean that he wouldn't be able to express his interest in some sort of obvious way. Even the really shy will express themselves in some sort of way such as a note or email or something. It sounds like it is just joking and teasing.

You can always ask him to join you for something that you already are planning to do and see how he responds and take it from there.

[sweet&simple]

I agree with the above.. flirting is natural, and it sounds like you're someone he's known for a while so, shy or not, he's comfortable flirting with you.

If he's flat out told you he's not interested in a relationship with you, he's not interested.