Jason and you weren't really 'friends' or anything. Dick introduced him to you, apparently you were an old friend off his. You both tolerated each other, yes, and you knew about him being Red Hood, you also knew of Dick being Nightwing.

He found himself texting you often to not be 'friends' with you. So when he found himself calling with you on patrol he knew he was smitten.

"You know when to contact someone on the most annoying time ever" He said throught the phone as he dodged a bullet.