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I actually had a very similar problem recently and now we consistently talk throughout the day. What worked for me was being relatable. Thankfully, I was on their private story and noticed they posted a picture at a concert where an artist I love was performing. So, I slid up and we talked about the music. People tend to like relatability, a lot of comedy is built upon that. Find that common interest and build on it. In the end though, find or make an opportunity to talk to them and be CONFIDENT.