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. 😊
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)).
Thank you. I have considered the option you suggested. That’s mainly why I am wanting to be careful about this. I did take your suggestion about inviting her and her son to an activity with my kids. We’ll see how that goes.