Overcompensating

When I decided to be a stay at home mom, I was scared of two things.
 1. That I would become one of those moms that ONLY talks about their "angel child" (when in reality the child is nuts) and 2. That my child would be that awkward, sheltered child that doesn't know how to socialize with any other humans and clings to their moms legs when ANYONE comes near them. I try to limit number 1, and I do my best to avoid number 2. (haha, I said number 2).  We do play dates as often as we can and we try to get out of our yoga clothes and go out into the big bad world as much as we can.

Most of the time, play dates are a blast. The kids have fun and the moms get to socialize and learn from one another. Other times, play dates turn into a circus and the moms never speak to one another because everyone is too busy playing the referee. That's not so fun.
The other night when my nephews and niece came over, things got a little crazy (as things do when there are 4 young kids around) and I could tell Isabelle was getting overwhelmed and she proved me right when she took her little toy and went to play in the hallway by herself.
That made me realize that there is such a fine line between "socializing" and "over doing it". It's nearly impossible to balance, but I'm learning her cues and even listening my inner self when I know that I've had enough and just need some alone time. Some days Isabelle is literally screaming with joy at the thought of going to school with friends and tells me that she wants me to "drop her" (that's Izzy talk for drop her off and leave her) and other times, she tells me that she just wants to stay home and play. I am happy to hear her say both of those things, but I am also confused by them. I think a little mothers day out program would be good for her, but I don't want to push her out the door before BOTH of us are ready for it.
Was there a certain time when you knew that your little one was ready?
Please tell me all your secrets.
That would be helpful.