Is my ex punishing me?

So you like the early letters, eh? Maybe that will be my New Year's resolution, to post letters before 8 a.m., even after I get back to the East Coast. I'm shocked that some of you are up at 5. You make me feel lazy.

This is really our last letter of 2010 because you'll get updates tomorrow. I'm thinking of you, in my West Hollywood hotel. I'm staying next to this. It's sort of ridiculous.

Roughly six years ago, when I was 21, I met J. I loved him, but I was not ready to settle down.
I often found J to be overbearing and sometimes obsessive about our relationship. We dated on and off for a few years before calling it quits when I met someone else. I lived with that person for two years and we just recently broke up. Over the last few years J and I would occasionally reconnect on birthdays, just the normal chit chat.

Fast-forward to now. I moved home a few months ago, and J found this out through mutual friends. He asked me out and we started getting together periodically, once every couple of weeks. Eventually, during one of our hangouts, I spent the night. The next day, I expected to hear from him, and the day after that and after that. Eventually I called him (I was not too pleased). I let him know that after all we had been through together (yes, I broke his heart but we did have wonderful moments) I thought he would have respected me enough to call. Needless to say we then had a very long talk. I apologized a million times and and we said that we loved each other, but he still wasn't sure.

We have hung out a few times since my outburst -- simple hangouts that have included drinks and a night spent at his place. Each time there has been an extended period of no contact before I hear from him again. He mentioned needing time, so I have not contacted him at all. I am letting him work this out at his own pace. Each time I finally hear from him, he seems to be more interested in the sleepover that comes after the drinks.

My question is -- how do I show him that I love him and that I'm sorry for the past? Is he just scared? Are these sleepovers his way of getting back at me?

– Not sure we can go back, Boston

You dropped J for someone else, NSWCGB, but you paid your dues. You apologized profusely. You've been attentive. At this point, he either wants to be with you or he doesn't. Tell him what you want, and if he doesn't want in, move on.
You could have handled the break-up better years ago, but you did the right thing. You weren't ready to commit and you wanted to be with someone else. Sounds like typical 20s behavior to me.
I guess I'm wondering whether you're pursuing J because you love him, or whether you're just having trouble adjusting to life after your most recent break-up. Are you sure that a relationship with J is what you want? Or are you just seeking his approval because you feel guilty and alone?
No matter what happens, start thinking about what you want and deserve, not what you have to do to win someone back. You broke up with J years ago, and for appropriate reasons. Keep your expectations high. This shouldn't be a chase.
Readers? Tough love for the end of 2010? Does she deserve to be toyed with because she left him for someone else? Is he not calling her after dates because he's scared? Is there a future here? Discuss.

– Meredith