On Valentine’s Day, a “friend” posted on her Timeline, implying she was looking for a relationship. I messaged her, suggesting that we give it a shot. We may get together over Spring Break (March). It gets complicated because we’ve only communicated on Facebook lately, after being school friends 15 years ago. We agree to go slow, as we’re vastly different people now. When we knew each other better, I was in a dysfunctional relationship with her friend. (I’m 4 yrs older) Truth be told, I was tempted to dump the gf for her friend. This friend has died, so there’s that dynamic, of possible “betrayal”. I’m unsure she even remembers the drama from back then. I plan to ask her about it.
tl;dr Contemplating dating late girlfriend’s friend.
You don’t need to talk about her. Just when you go on a date, ask for a table for three, pull out an empty chair long enough for the dead ex to sit down, and include her in the conversation.
I’ll go along with the flow here - I don’t see a problem. Don’t bring up the late lady yourself, but if she broaches the subject, respond with compassion.
Reading this, it is unclear as to what her response was to you asking her out. What did she say? Did she give you a “maybe” answer? A definitive “yes”? What? I’m sensing no definitive answer here. Which makes me think all this hand-wringing and nervousness is *a bit *premature.