Look, Anna is a bit of a disaster when it comes to follow-through. When she and Elspeth met on an app, it was such a change of pace from disastrous dates and personality mismatches. They hit it off. Like, they REALLY hit it off. Anna had real feelings for Elspeth; she was super into her wit and resourcefulness. The problem was, Anna had no real tools to deal with loving someone, and with hindsight, maybe, she can now see that Elspeth didn't either. They both pulled back from this great, promising thing, and now, for the most part, Anna pretends Elspeth doesn't exist. Yeah, she knows it sucks. She knows it ended poorly. But you see, whenever they see each other now, like at parties, they either sleep together or try to be friends but then the feelings come back and she can't!! do!! these!! feelings!! so it all falls apart all over again. Basically, Elspeth is a tangible representation of Anna's desires, failings, and unfulfilled dreams. Don't ask her about it unless you're both drunk.