What I Learned from Stalking Katie Holmes

I only meet a handful of girls that are attractive to me, so when I miss opportunities I get really mad at myself.

This past Friday, my friend Margaret and I were walking home to our apartments after work. As we approached Third Avenue on Twelfth Street, we noticed a throng of paparazzi gathered outside the apartment building that was formerly the American Felt Building.

Margaret knew exactly what was going on:

"That's where Katie, Tom, and Suri live," she explained.

OK, even though I'm not on a first-name basis with Tom, Katie, and Suri Cruise like Margaret apparently is, the chance to see A-listers was a bit too tempting. I got giddy.

"Well then, why don't we stick around and see if we can get a sighting," I asked her.

I was more interested in impressing my little sister. Actually, I planned to send texts to everyone after I saw Katie (I'd be allowed to be on a first-name basis with Katie after I saw her).

The crowd continued to build. After about half an hour, there were about 100 people gathered around. Two girls walked by the front of the building and then decided to stop and watch and engaged us in conversation.

One of these girls was a striking blonde. We chatted for a bit, and I actually remained cool for once but, as Margaret put it, I "wasn't flirty at all."

Eventually Katie Holmes came out and jumped into a waiting SUV and was on her way to perform in her Broadway show.

Apparently Katie didn't smile enough because a passing gay man(if he was straight he was very feminine) made an angry remark about how mean she was. I did a perfect impersonation, and the girls broke into laughter.

So this is where I made my move right? Nope. I told the girls to enjoy their weekends, and Margaret and I were on our way.

Afterward, I asked Margaret how to turn these sorts of opportunities into a date or getting a number. Margaret mentioned that the deck was stacked against me because it looked like she and I were dating.

What needed to happen was a change in conversation topic. We had to get the conversation off of Katie Holmes and on to the actual girls:

But Margaret pointed out that this kind of transition would be awkward.

This leads me to the subject of Margaret's development into my "wing-woman."

She demonstrated that she has reached the point of knowing who I think is attractive. She needs to take the big step to the next level: managing my public relations by putting me in a great light. She could have helped with a statement that made me look good and sparked conversation into the right direction to eventually get me a phone number.

Quality wing people do this. If I am to get a wing-woman other than my sister, I'll need to train her to understand the seamless silent communication that happens between a guy and his wing-man. I think girls are capable of becoming quality wingers, but that intangible communication that is natural between people of the same gender must be taught if it is to happen between a guy and a wing-woman.

My failure was by no means Margaret's fault. It was just a good opportunity for her to develop into an official wing-woman, but it didn't happen. There will be more opportunities, and we learned from this.

So here I was again walking away from a girl I thought was cute, had a little "in" with, but did nothing.

At least I saw Katie Holmes, and — yes — my sister was impressed with the sighting.

What should I have done here? Can you help me figure out how to make this transition from light conversation into getting a number or getting a date? I've never been good at this, sober and not in a bar. But because of my pickiness and bad luck, I need to seize more opportunities because they are rare. How many times do you think I need to do this before I reach that magic numb point where I don't fear rejection?

Is it just plain creepy to hit on a girl in this situation? Do you mind being hit on at times like this?