I said it first when I felt it and didn't expect to hear anything back in return. It took him a bit longer but he said it. I was okay if he didn't say it. Life is too short for me to live in regret. Perhaps, if I didn't say it, he would have taken longer given his dating history.
I love how you can articulate your attachment styles and its effects on your behavior so clearly. I will have to analyze mine more closely. I think I am somewhere in between an avoidant and secure depending on the situation.