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. 😊