Dear Meredith,
I really need your help with this one. I’m good with my friends’ problems but never with my own. Ok … here it goes ….
I’ve recently reconnected with a guy who I’ve tried to forget for several months. A little background story:
The Past:
We used to work in the same company (I left) and I would see him almost everyday but we rarely ever spoke to each other. At the time, I had a boyfriend so I left the attraction alone. When I was leaving, I joked with him to let him know (this is when my bf and I had been broken up for two months) that I was leaving. Our mutual friend actually convinced me to give him an opportunity to date me. So we exchanged numbers.
We spoke for quite sometime and went on a few dates. However, as time passed, we began to see less and less of each other. Unfortunately, he is a workaholic (like 8 a.m. to 1 a.m., seriously). Our plans just didn’t go through and there was always some random excuse (Later, I found out that he had a girlfriend and they were having problems. Great! I know).
I basically told him that because he is so busy, I just can’t see us even being anything but friends. It ended with him repeating the same things that I said to him but in a more exaggerated form. I guess it was some sort of payback.
The Present:
Ok … So a month ago, we spoke to each other again and to be honest, I haven’t forgotten about him. I found out today that he broke up with the gf a few months ago. We flirt like crazy. He tells me that I’ll always be special to him. He calls me these pet names that make me feel awkward because things shouldn’t move that quickly. We are friends (I am not going to lie and not admit that I don’t want more because I do, but I would like to take MORE time to see if there is any point left of trying to pursue anything).
But … it seems like the past is repeating itself … our plans didn’t go through again. He thinks that I’m mad because the plans didn’t go through. It’s not that — it’s that he didn’t let me know ahead of time.
I also feel like he is hiding a lot of things from me. I requested him as a friend online and he told me that when he logs on again he will add me. Let’s just say I know he logs on but he doesn’t know that I know he does. It doesn’t matter if he does or does not add me, but be honest about it. I don’t think it’s wrong to tell someone that you don’t feel comfortable adding them. I did the same thing with my exes when they were my boyfriends. I didn’t feel comfortable adding them because there is always some sort of drama online.
He tells me that he is making changes in his life that he can’t tell me, but will free up his time.
Basically, I am trying not to start conflict with him over things that I could be over-analyzing. I’m just a very outspoken person and I believe that I have tried telling him in subtle ways that he needs to know what he wants. He told me that he fears rejection, I do, and everyone else does. But that excuse is so over-rated.
I just don’t know how to approach him to say, “I would like more, and we need to make definite good plans if you like me,” without sounding like a desperate individual. Or I wish that he would just tell me “I just want to be friends.” He is very good at changing the subject, too.
Thank you and Happy New Year!

– Name Ms. Temporary Ambivalent