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How do I talk to someone I've had issues with before?

I wrote three paragraphs but it got deleted. Oof.

So, last year someone found me annoying. No grudges! Just "I wouldn't choose to sit next to him." This year they don't find me annoying, and I try to talk to them but it ends up being very awkward. I'm a guy, and she's a girl. That makes my various attempts start to look either very desperate or very thirsty. How do I start a conversation? I've been told I'm incredibly engaging to talk to, but finding a topic is really difficult for me.

I'm trying to talk to more people, like my therapist told me to, and I know we have similar interests, but it's very difficult for me. I end up just saying "How's your day been?" and getting an answer I can't really respond to with anything other than "that's good."

I have BPD, if it helps. Thanks guys.