The Boob Crusher (3rd Date Investment)

One night I was out on the town with my male friend (The PM) which already makes the odds of meeting another guy pretty slim hence we went to my favorite place for men - PS450.

We were drinking at the bar and scoping out the people, commenting on appearances and behavior of the young professional crowd. It's pretty amusing to observe really.

That's when I saw a good-looking, well-dressed, 6'3 (my ideal), shy guy standing alone while his friend hit on some girl with bad taste in shoes.

Some time later and half-way into my Very Berry Mojito, PM urged me to approach the bored-looking boy. This is something I don't know much about since they usually come to me and wow does that take courage! PM told me what to say - nothing complex or anything but I was glad that I didn't have to think of anything nonetheless.

We hit it off and exchanged phone numbers. He seemed interested when he called and we immediately set up a date for later on in the week - a good sign from the start.

I think I've turned a new leaf when it comes to being the pursuer... I kind of like it!

After two dates with lots of talking and no physical contact (no kissing - nothing), I knew we had to step it up on date # 3. This guy was a catch - Tall, Good Family, Sound Job, Compatible Religious Background, Solid Private School Education in a Ritzy Community, and we had hours of conversation without a hint of the normal dating interview question & answer session.

I consulted with PM about our dates and he asked me a question that I never thought of before - did you offer to pay? I didn't and I don't think I ever have. I was always told not to and even my male friends have paid for me.

After a major discussion, we decided to survey some people we know on the topic. To my surprise, the majority of people we asked think that the woman should offer to pay even if it's insincere. It's like a test... if he let's the female pay, never date him again! Personally, I don't get it. Why ask a question that you don't want the answer to? But that's another story.

There I am on my way to my 3rd date and in my mind the tests are coming. We went, we talked, I offered, and he actually accepted!!!

I was shocked... but I had to see if there was any physical connection after I panned out the dough (hold on - was I turning into the man in this?)

Finally we went to his place and kissed. It was terrible. Not the kiss itself but everything else. His apartment smelled like B.O. and mildew. He grabbed my boobs so hard that they hurt the next day and everywhere that he touched me felt like probing.

I actually got out of the clasp by claiming that I needed to use the bathroom and giving some lame excuse when I got out. "It's getting late. I think I should go now."

So, if you're at a bar and you see a good-looking guy standing alone, there's probably a great reason for his lack of confidence. Don't date him New York.