Q: The mom of one of my son’s classmates wants to pick him up from kindergarten for a playdate. I don’t know this woman or her home. Should I let him go, or break his heart and say no? Consider this the first in a series of many times you will break his heart—for his own good. It can be awkward to finagle a peek at the scene of the playdate, but you need to know as much as possible about where you’re sending your child. Just because the mom seems nice when you bump into her at drop-off doesn’t mean her sense of responsibility matches yours. You might wonder: What could a house possibly contain that would be so horrible for a measly three-hour get-together? How likely is it that they have a rabid dog or a dungeon in the basement? Still, there are legitimate concerns, like older siblings using colorful language. Sometimes the minute kids get home they turn on the video games (and that’s not how you roll). Sometimes there isn’t even a parent present, but an uncle or an older cousin, and the person chaperoning the playdate isn’t the person you spoke to at all. Some people keep guns in their home. The list goes on, and you’re entitled to call the host mom and ask all your questions. If you don’t like the answers, turn down the invitation. But if you’re not comfortable being that direct, there are other ways to do some research. You could call another parent who knows the host or her home. You could also counter with an invitation of your own. You might say, “It’s not going to work for me to have Jordan go home with you that day, but what if Michael comes here?” Then you could invite Michael’s mom in for a cup of tea, with the hope that she’ll do the same when you drop off Jordan. Of course, she may come right back at you with an excuse, because now she’s uncomfortable with the arrangement. Congratulations! It’s a match.

Q: My 2-year-old daughter loves playing with the girl across the hall, but during the week, the girl’s stay-at-home mom never wants to make playdates with our nanny. Is this playdate not meant to be? It’s the rare mother who will playdate with a nanny. Why is that? Because for most stay-at-home moms, de-isolating is the number-one concern—who their children socialize with is secondary. Socialization is socialization, and unless the other child is ripping the heads off dolls or chasing your daughter around with a switchblade, there’s not a lot of soul-mating going on in the 2-year-old playdate set. It’s about mothers wanting to get together, and that’s fair. While it’s too bad that your neighboring mom doesn’t want to grab a latte and head to the park with your nanny, that’s her choice. Still, the girls can play together on the weekends, when you’re home. You could also invite the mother and child over for a playdate when you and your nanny are there together. Include your nanny in the conversation so your neighbor can see how she is with the children. If your neighbor starts to feel comfortable with her, she might be more amenable to a playdate. Or at least she may be open to letting her child play at your place when the nanny is there and she’s just across the hall. They could even switch off. It just might be the start of a beautiful friendship.