Alright, so my son is friends with a kid at his school, and through this I met his mother. She is a nice woman, who is attractive and friendly. What I do know about her is that she and her husband are separated and/or divorced. I do not know if she is seeing anybody.

I have an unsuccessful history of assuming things with women who are nice to me; i.e., I often confuse being nice with them showing a romantic interest, and that not being the case. Given that my son and her son are best friends, I do not want to make this mistake and make things awkward for anybody. Given my unsuccessful history of reading social cues, I want to be careful in how I interact with her.

I feel like I have three choices right now: I could continue my current course of action, and interact with her when my son and her son get together; I could text her and try to strike up a conversation out of the blue; or I could add her as a Facebook friend and from that angle try to strike up conversation.

I don’t necessarily want to go the “do nothing and hope it works out” approach, but I am not sure if I would make her uncomfortable by being too direct. I’m kind of leaning toward the Facebook option, but I am curious if I should ask her if she’s ok with me requesting to be her friend (and possibly sparking a conversation that way, but letting her know it’s okay to say no if she’s not comfortable with it).

And before anybody says it, yes I’m aware I’m probably overthinking it. 😊

  • @dohpaz42OPEnglish
    2•4 hours ago

    I did fail to mention that last night, when dropping my son off to trick or treat with her son, she invited me to go with them. I had to decline because I was taking my other son trick or treating elsewhere.

    • @paddirnEnglish
      2•4 hours ago

      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.