We (DH and I) have friends that have recently moved up to that status (that of "friends") in the last few months. They were acquaintances for almost seven years, though. We have a daughter and they have a son about the same age. The kids play together really well.
Since the friendship for the whole family is new, we've been having get-togethers. Either both whole families get together, or one adult from each family plus the children.
The woman friend, let's just call her Dee, has asked a few times if DD could come over by herself. The first time she asked, we asked DD and she said she didn't want to - I wasn't surprised; DD had only been over their house once at that point (mostly mutual playdates at the park before).
Now DH is not a trusting man. He is not of the "humans are basically good" tribe. He is suspicious of motives. He is fiercely protective of his family. And he has some good reasons to have come to this (I can already hear people criticizing my DH). So the first time Dee asked DD to come over by herself, DH's antenna went up. It bothered him that Dee asked this. No, not like "I'm ending the friendship" bothered, but just like wanting to talk out with me what could have spurred this request.
Now, I trust Dee very, very much. Our friendship may be new but they (Dee and her husband) have very similar values to us. She is a calm and good mother. And DH was actually the one who decided to kind of bring the acquaintance to the level of friendship, and he did that because he thought they were good people. He is not a man to just hang out with anyone.
I told DH I thought Dee wanted DD to come over by herself to give Dee a sort of a break. Since the kids play together so well, they could entertain each other while Dee maybe got things done around the house or did a little reading, knowing she could just keep an ear out for the kids. The reason I thought that was because I've had that urge myself :) To have a kid come over and engage DD while I did my own stuff, and a playmate that fit well enough that there aren't fights or trouble is hitting the jackpot.
So DH asked Dee if she would like to drop her son off here for a playdate. Ostensibly this would give her a break as well. But her son also did not feel ready yet to come over by himself.
So the matter got put to rest for a while but then it came up again. Dee asked DD if she felt she was ready yet. DD said yes (which might be true, but it's also possible that when it comes right down to dropping her off, she might change her mind, dunno). So now DH is scratching his head again trying to figure out Dee's motives.
I think he also posted this question on some forum somewhere, and he got mixed responses - some thought he was crazy to have any concern about this, but others thought he'd be crazy to drop off DD with a woman who obviously has some agenda to get DD alone (lol). On the last bit, I have to agree that Dee does have some sort of motive, it's not just a passing thought, she's brought it up more than once. Of course the motive may be entirely innocent (I'm still sticking with the "break" scenario myself).
Well, what do you think? It seems obvious that I should just outright ask her what her motive is, but it does seem awkward. We are not close friends, just beginning a new friendship.