Jen Renee asked:


I have this buddy that I’ve known two years, but we didn’t start hanging out outside of work until a year of knowing each other. We would go out with two other friends until two months ago when I made a move and one on one dinners started. A lot of things have progressed and everyone I know is convinced he likes me, but I’m still not sure. He hasn’t kissed me yet, but he spends hours and hours with me, always pays for dinner, he’s always finding a reason to touch me, always suggesting things we should do, etc. So we’re not dating per se, but he’s constantly making little moves but nothing major. My friends say it’s because of the fact that we started out on a friend level and he’s not sure what I’m thinking and is afraid to mess it up. So right now he’s testing me out and waiting for me to make the move.

Last weekend I mentioned that I’ve never celebrated new years and he said, “Do you want to celebrate with me?” I also told him how I was going to be down in Florida but obviously didn’t go, and now he wants to do that with me as well. He told me he’ll call up his friend down there and figure some things out and let me know. He told me twice that his two week vacation starts Dec 23.

Knowing him, I’ll probably have to text/call him and ask what’s going on. While I understand that I’m the planner and that he’s the spontaneous “let me know the day before” person, I don’t get it. Why make plans but not follow through to confirm but instead want me to do that? Is he really unsure of what I’m thinking/feeling and wants that to all be in my hands so he doesn’t get hurt? He has to be interested in actually going out on new years and going to Florida if it was his idea and he made a point to say when he was off and how he’ll research some stuff on the internet first.

During our last dinner he also mentioned the fact that I’ve only been out drinking with him once. Once again, I have a feeling I’ll have to contact him first because he seems to want me to make all the moves. Should I just text him and ask him if he wants to go out drinking later this week or something else?

I don’t think this is a “he just wants to be with you whenever he feels like it” situation because he never ignores me, always follows through with plans, and he’s always the one to be like, “let’s do this.” In fact we had a discussion about other people we know and he made sure to bring up the fact that he’s never let me down (which is true).