That sounds innocent enough that it could go either way. It could easily have been just an innocent thing to have another adult along to hang out with the kids, women tend to not think anything of inviting somebody out to do something like that and don’t necessarily have an ulterior motive. It could mean more though, but it doesn’t seem like a big enough data point to go off of.

I think there’s a leap here that you’re not explaining or that I’m missing from the text. She sounds attractive and friendly, she’s apparently “available”, but what is prompting you to wonder about a course of action? What’s the trigger? Has she already behaved a certain way towards you that’s making you question if there might be something “there”, like she seems to be extra “nice” to you or whatever? Or are you just wondering in general, “Hey, there’s a person I’m attracted to and I want to see if she’s interested?” There just seems to be a disconnect in what you wrote and I’m not sure what prompted it to begin with.

To answer the question though, you can certainly try any of the things you talked about, or try to setup a meetup between your kids, but somehow include yourself and her in on the plans (go out to a movie together or some event) and see if she’d want to join you all. Personally, I wouldn’t try to force things too far and make it awkward, but if you’re trying to gauge interest, you should try to figure out ways to spend time around her or start finding reasons to text to ask about stuff. You also have the issue that should things progress between you two, do things get awkward between your kids anyways, even if you and her hit it off? It could potentially cause friction for them no matter what happens. Relationships are hard no matter what.

I find happiness getting lost in projects, projects being anything & everything from writing to designing to stuff around the house to whatever. Just something that gets me obsessed for at least a few days or weeks. I can’t predict when it will happen, it just has to be a sufficient problem for me to look at.

I also find happiness with some people, but that sort of happiness is unpredictable as well since people have their own lives going on and feelings can change over time. Getting too close to people though can just as easily make my life feel meaningless and make me depressed when things turn sour. I tend to crave affection and physical touch, so this is a hard one for me to just ignore this.

I went out with my kids and we went to a few houses actually that had lights on outside and inside, told my kids to go to the door and knock, waited a minute or so, and nothing. This was maybe half-a-dozen houses, so it’s not always a given that just knocking on the door will get results. The new “normal” is that people are either waiting outside to hand out candy or they’re leaving bowls out for kids to help themselves. Knocking on the door for trick or treating is a crapshoot and it’d be understandable why most kids will skip that. Compared to other houses, it’s more effort for potentially no reward, or, even if there is a reward, it’s the same as every other house.

If a girl doesn’t like you, but you just keep pursuing her, everything will eventually work out and you’ll be happy together.

Our boss just took us out to lunch and gave us four hours off the rest of the day to go out and vote, which is probably the most encouragement to vote I think I’ve ever gotten from any boss before. I’m sure I was entitled to it this whole time, but it’s never been encouraged like this before with this boss at any of my other workplaces, if anything, previous bosses probably would’ve talked shit if I said that’s what I wanted to do with my time.