I had a 3rd date with this guy who is a criminal attorney. Now, one would think someone who works in this field would exude confidence, right? It should come with the job….. Plus, attending a top-tier law school and having a job that generally WILL attract women should boost self-esteem.
Not this guy.
He took me to Greenhouse Tavern, which is one of my favorites and I was optimistic that it would be a nice Friday night. I was wrong.
Halfway through a bottle of wine and a few bites into my steak this guy goes “So, I have to ask you something.” I just had a feeling I wouldn’t like this. He continues… “Now let me know if I’m wrong, but I have a feeling you’re on the fence about us. Like you’re not sure if you like me.”
I choked. It’s the 3rd date. This is what dating is for – to determine if you are compatible with someone. True, I am not sure if it would work with this guy. From date one, his apparent lack of confidence was the sole reason why. He’s tall, cute, successful… but he’s a guy I could walk all over. I don’t want a guy I can walk all over because it bores me. He wasn’t proving me wrong.
Although it made the remainder of the dinner rather awkward, I replied with an honest “I’m still getting to know you and trying to see if we are compatible.”
Then he goes into a “Most women want to like me, but in reality they are just being nice and really don’t” tirade. I kept trying to change the subject, but he kept going with his “No one wants a nice guy” spiel. It ruined dinner. I didn’t know what he expected me to say, so I didn’t say much. I just sat there and awkwardly nodded. Eventually, I managed to get on another topic. Yeesh.
Afterward we stopped at the bar next door for a nightcap. Once again, he began asking me if I thought I liked him or not. If I wasn’t sure, why wasn’t I sure…. I was highly agitated at this point. Finally I couldn’t take it anymore so I responded… “Do you want to know why? You have zero confidence. I don’t understand how you even perform your job with such low self-esteem.” I went on to explain how I’m a very brash, animated kind of person and I need someone who can keep up with me. Lacking confidence isn’t going to work. I don’t want to be with a push-over.
The conversation went on for a bit longer, and then finally I became so frustrated that I bluntly told him to “Grow a pair.” I didn’t even care anymore – his constant need for affirmation was so unattractive.
He keeps texting me. I don’t think we’ll be going out again.



