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.
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.
That’s an excellent idea. “Fun activity for the kids” is a great way to get the ball rolling. If the ball doesn’t get rolling, you’ll still have a pleasant afternoon and it won’t be awkward.
“I think you’re pretty. Wanna bang?”
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.
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.
