It's not unusual to hear stories about children who cry before, during or after a daycare drop-offs and pick-ups. The stories I've heard come exclusively from mothers who often weave their feelings of guilt into the telling. Interestingly, if dads are experiencing these tears, they're not telling me about them. Maybe they just don't think the stories are worthy of being told.
I remember one time when my son, who was about seven years old at the time, cried when I picked him up from a new summer day camp on a Monday afternoon. As he climbed into the back seat of the car, backpack in tow, I asked, "Well, how was it?" That's when he got a little misty-eyed and started to tell me a sad tale about how things hadn't turned out as he'd hoped; he had wanted to make all new friends for the week, but after arriving that morning, he realized that he already knew one of the other kids in his group. And apparently that child had wanted to play with him; all day. I did remember that "all new friends" had been one of his requests, but didn't realize the earnestness of it. Apparently the presence of that single existing friend meant the experience had been a significant disappointment for him.
I share this story because it just goes to show that, like adults, children can be complicated beings and their emotional reactions can be somewhat befuddling at times. I was quite certain that there was no reason I needed to feel guilty about not being able to find a daycare situation consisting exclusively of strangers. It seemed like an unusual, and maybe even naive, request at the time. I'm not sure I even took it all that seriously.
When we require our kids to participate in activities and interact with people beyond the family, we start the process of introducing them to the world and teaching them to navigate their way through it. Regardless of our best efforts, they will have good days and bad days. They may even have good weeks and bad weeks. As adults we know we may even have good years and bad years. That's life.
It's our job to keep our kids safe while helping them to explore new situations and develop a variety of coping strategies. When they cry while encountering new situations, rather than feeling guilty, we should embrace the situations as teachable moments if we can. But like everything else in life, that can be a lot easier said than done.