Milan being Meredith yet again

Today is our last day of help from Bruin Milan Lucic. Video is up! (Sorry for the delay.) I think that with today's advice, he scores a hat trick. You'll notice that he references "He's Just Not That Into You" in his final answer. I swear he did that all by himself.

We'll skip today's chat. I know you all want to bail from work early (and should).

Again, tickets for the Love Letters/Movies event are on sale. We'll announce pre-party information soon. And the bracket with the films should be up early Dec.

As for tomorrow and Friday, I'll post some updates.

I stumbled across Love Letters last fall when you published a story about a girl who had moved in with her boyfriend and he broke up with her rather abruptly. A friend sent me the link and I've been hooked ever since.

Moving to New York has been, without a doubt, the biggest change in my life. I'm still adjusting to the pace of the city and trying to find my way around a place where I don't know many people. Up until I moved here over the summer, I hadn't been dating for nearly a year -- a direct result of having gone through a nasty breakup with the Ex. Given that I'm in NYC for the long haul, I figured -- what better way to meet people than through dating?

I'm naturally a very shy person and have difficulty approaching people out of the blue, so I thought I'd try online dating first. As you can imagine, I met people who ran the gamut of sincerely nice to the disgustingly insane. There was one person who stood out from all the rest. He had e-mailed me to tell me he liked my profile, and while I wasn't interested at first, I decided to exchange e-mails with him. We corresponded for about a week, and since he wasn't mentioning it, I asked him out for coffee. He agreed to it with the tone of someone who at least sounded interested in meeting me.

The first date was fantastic, although I felt like I was left a little out in the cold at the end of the night when all I got was an awkward hug. However, a few days later, we made plans for a second date, which was just as great as the first. We spent all afternoon and evening together, and it wasn't until I realized that it was midnight that he suggested going home (separately, of course!). I had had a great time on both dates, and it seemed that he enjoyed hanging out with me too, but after the second date, I haven't heard from him at all.

Part of me worries that he wasn't really that interested in me. After all, if he were, he'd at least call or text, right? On the other hand, when we were together, everything seemed to point to him enjoying my company and wanting to see more of me, even going so far as to mention other things we could do "for next time." He did also mention that he tends to feel socially awkward at times, and doesn't always feel comfortable interacting with women.

All that being said, what do I do? It's been more than a month since our second date, and while I think it might be too late to follow up with him, I think he's a really great guy and someone I'd really love to know better. On the other hand, if he's not interested I don't want to be pushy and/or clingy where I'm not wanted. Help, please!

– Should I Call, New York

SIC, if you really need to send a note to make sure that your signals weren't crossed, fine, but I'm going to guess that it won't change anything.

He sounds like guy who's more comfortable e-mailing that asserting himself in the real world (after all, you had to initiate coffee), and I think that you're better off continuing to date other people until you find someone who prioritizes clarity. It'd be great if you found a guy who respects your time and makes it known if he wants to see you again. You shouldn’t have to waste so much energy guessing.
So, yes, send a quick note if you need closure, but balance that note by sending messages to a few more guys online. New York City is a big place populated by assertive people who know what they want. Living there isn't always easy. Try to make dating a bit simpler by walking away from people who confuse you.

Readers? Should she call? Should a shy person pursue a guy who feels awkward around women? Is online dating a good way to meet people? Discuss.

– Meredith