ETA: I think small talk is good, and there is nothing wrong with asking about family and school as long as it is not too personal.
I wonder why you feel it's awkward?
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I think it depends on the age of the child.
Offering food/ toys, not OK by my standards.
This is different from 'small talk'.
Any normally functioning adult would know not to offer food/toys to small child without at least addressing the parent first. Otherwise it is a red flag to me (should I continue to see this other person).
I think these type of situations present a great way for parents to see how their children interact with others. This allows the parent to see the child's comfort level and sense of boundaries and then discuss with the child if there is any concern.
We had a man hanging around baseball games this summer. It was the uncle of one of my son's team mates. He have me a bad feeling in my gut, but not much else about him was concerning.
About halfway through the season and having no verbal communication with him, he approached my soon to be 12 year old son. He was reading about 5ft away from me on a blanket while we watched my younger son play. My older son has a very profound speech impediment and cannot get words out right away or 'speak up' right away should something bother him, and he has a rather passive personality. So I feel he is a bit more vulnerable.
So anyway this uncle approaches my 12 year old and strikes up a conversation about what he was reading...no biggie. I think it's 'more normal' to also acknowledge parent, but whatever.... Until I hear him asking what grade my son is in.....where does he go to school...what's your name...what part of town do you live.....(what? Oh he// no...)
So I watched how my son handled it, and despite all the 'stranger' talks I had with him he felt giving the adult the respect of answering was more important then his gut feeling that the questions were too personal....So my son knew it was inappropriate he just felt powerless to set his boundaries. This is what all stranger/danger books and programs can't really teach.....
After the game we discussed the situation and how to handle it better, and that it is ok to set boundaries even if it comes across as rude.
Having been molested, and having been around sex offenders I can tell you at least 90% are male, and that about 80%will use friendship/ relationship to lure a child (to get in between the parental child boundary), and about 2/3 of child victims are female.
Again, you cannot control other people's behavior and 95% of small talk *is* harmless chitchat, but I think it's a great "live" opportunity for a parent to teach their child about boundaries and comfort levels.