Ask Lemmy

I feel like "don't try to get with your kid's best friend's mom" is also an option that should be on the table.

That said, don't go the Facebook friend route. The intent is too ambiguous and doesn't get you any closer to your goal. I'd favor either the direct approach (the classic, "would you like to go out for a drink sometime?") or tie it to an activity you'd both be doing already anyway ("My son and I are going out for pizza after the t-ball game, would you and your son like to join us?" (I don't know how old your kids are)).

I don't think social media works well for these kinda things, but you could pick an activity you think she and her kid would enjoy and invite her out. Something casual like a museum or park. Take the temperature there and see how things feel.

My adage with dating is to err on the side of gaining a new friend as your goal. Then the worst outcome is you get a new friend.

Do nothing / don’t show any romantic interest.

Get to know her better as a friend. If she becomes interested or is interested in anything more, believe me you will know.

Seriously, just forget about any romantic possibility. If she is interested then she will make it happen… otherwise you will just ruin your son’s friendship for no reason.

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.

Seems like if she's interested, she might invite you in for a drink or coffee next time you drop your kid at their house. If she's too shy, maybe you offer next time she drops her kid at your house. If she stays in her car as little Billy runs up, that's a sign she's not interested (or just busy at that moment).

I also like the idea of offering to take the boys to a movie or something and inviting her. But she may just want to see a movie, so that's not a total green light. If she grabs your dick during the movie though, that's a pretty good sign.

"I think you're pretty. Wanna bang?"

Ask her what her favorite steam locomotive engine is.

Get upset when she gives the wrong answer.

Erupt into a heated diatribe about the necessity of good boiler design and make sure she knows why she isn't allowed to be friends with you.

Yell something unintelligible at her son on the way out.

If she still comes back to you later, then you know you've found a keeper.

Maybe ask about the dad when you next meet up? Should open up the conversation.

Could ask if she and her son wants to get dinner sometime with you and your son. As long as it's a pretty inoffensive family restaurant, that shouldn't be too forward. From there you can get a better understanding of her situation.

Meh people are gonna come down on you in this thread for not being some perfect picture of a parent/person, but you are considering things, trying to find the best path to be respectful and decent. It's ok to acknowledge your wishes in a "private" conversation where you weigh the consequences of things.

Imo this is your son's relationship with the friend. Let that run it's course, and just read the signals along the way.