His friend is mine as well and has been for 2 years. We all work together. "Our" friend is always pushing him to take me out and do things with me and he'll do it right in front of both of us. He does not mind calling you out! Just today, he pointed directly at my head and said, "Is that a pimple?"
When I had my 5K, he asked him if he was going to go to support me - that should be the first thing any person would think of. My boyfriend is the type of person who won't do anything unless you bring it up/suggest it. Of course he hadn't. I knew better than to ask him because I knew he would find a way to let me down. Things that have happened to me in the past has caused me to be traumatized so I don't even bother to ask him.
I've got him in training right now. He keeps asking, "When are we going to hang out again?" I just tell him, "When you ask me" or "Why don't you think of something? Let me know what you come up with and I'll make sure to clear my schedule for you!"
I'm usually the one to make plans for us, because his procrastinator tendencies would fail him in that area. I used to be so easy and do it, but now I've taken up hobbies and am teaching myself Korean as well as relearning Spanish (took it for 7 years and still can't speak a word) Our friend is helping me because he is Hispanic and a native Spanish speaker. Bikram yoga and barre classes start next week - so I keep myself busy. Meanwhile he's wondering why I'm not so available anymore or wanting to spend time at his apartment (cheap date). I've told him this for 9 months. He suggested a movie and we went - 2 weeks ago, but haven't done anything since then. I was sick last week and TOM is in town this week (I go incognito and he knows to leave me alone and that as a Crab I go into my shell). I'll be on vacation in New York with my brother the week after next. I'm okay with taking this as far as I can until he's fully trained in speaking up and showing that he wants to spend time with me.