"Where is this going?"

That's what I naively asked my first college "boyfriend" after we had been "hanging out" for a couple months. Big mistake. Huge. (Did anyone else say that in a Julia Roberts/Pretty Woman voice? I hope so.) He totally wigged out and didn't talk to me for a month. And that, my friends, set the precedent for our two-year rollercoaster relationship. (Hello, red flag!) I later learned that I had opened the floodgates to having THE TALK. I had no idea it was such a big deal. Geeze.

There are so many stages to dating—I just gets exhausting. The "talking" phase is the trickiest. You like someone, they like you, you have fun together, so why is it so gosh darn hard to make that next step? Well, that's exactly how I feel about making new friends as an adult.

Gone are the days you proposition someone with a lick of your ice cream cone or just flat out ask them to be your friend. (Btw, if anyone wants to be my friend, the ol' ice cream trick will TOTALLY work.) It's frustrating because I have a lot of friends in NYC that I'm in the "talking" stage with, but I just don't know how graduate to the let's-hang-out-in-our-yoga pants-and-watch-movies-on-a-Sunday-night type of friend.

Or, am I just being greedy? I do have lots of friends here, and a few that I know will be in my life forever, but I'm still constantly searching for more people I can truly connect with. I used to be embarrassed to bring this subject up (I mean, who wants to admit they want more friends?), but I'm finding more and more that it's something lots of people want and struggle with later on in life. Take Rachel at MWFSeekingBFF for example!

So what's your advice for me readers: How do I turn casual friendships into the real thing? I know I can't just flat out ask "WHERE IS THIS GOING?!" but oh, I really want to. And where are you on the friendship-o-meter—are you happy with what ya got or do you wish you had a few more pals? Oh and does anyone have a good story about busting out the "talk" with a guy?