She probably keeps asking about the job search because that’s all she knows about you and doesn’t know what else to say. She’s not too tactful. If you tell her you’re on disability, she’ll keep asking you how’s the disability going. It’s all none of her business. I’d keep telling her I don’t want to talk about it. Eventually she’ll get the hint. Or answer her with something totally different like you’ve seen a good movie lately, giving her something new to talk about.