My boy is almost three. He's generally shy and clingy for ten minutes or so in a new situation and then turns into a whirlwind. His reticence is awesome, his best friend isn't shy at all and his mother has to constantly chase him down in new situations, whereas we can go to the zoo or a store without fear of him running of or getting distracted.
Making progress away from Velcro... He has been with babysitters while I work since five months. With his first babysitter he cried for three days. With the second (at nineteen months) he cried for two days and then 3/5 days a week when I dropped him off. At twenty-five months he started day care and... didn't cry at all on the first day. I felt like we'd rounded some sort of crazily-unexpected corner. Two weeks ago we started attending athiest church. We brought him to "Sunday school" and left him there without tears, and although last week he was sobbing when we left him, it only lasted five minutes and other parents reported on the incredibly smiley little boy they had meet in the classroom. My yardstick for whether he actually enjoys a place is how he acts when I pick him up. If he doesn't want to leave, then I know he's enjoying the place.
That's pretty much how it goes. Everything is either super-sunny or super-stormy, in a way that we'd think was normal if we never talked with other parents. He's incredibly generous and rarely ever has a problem sharing or giving up his toys to others. Others remark upon his generosity of spirit. He has a new baby sister whom he adores and kisses and tries to soothe and care for all the time. He loves other babies he meets out and about. We're terribly afraid he'll go into social services and not be our back-up retirement plan in a better wage-earning field (joking!).
His baby sister is almost three months old now. It's bizarre because she rarely cries and, although she prefers to be held, will entertain herself for twenty or thirty minutes watching her mobile or life go by. Unlike her brother (who was speech-delayed which did not help him be less Velcro), she is already working on figuring out how to babble and coo.