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First Date: So Confusing!

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After emailing a guy for six months (a long-distance “friendship.” We’re both in our mid-thirties, and both workaholics), we finally found the time to meet up. I was in his city; he texted if I want to meet up for drinks. He was approximately thirty minutes late, as “he got stuck in a call,” He was also badly dressed (jeans, wrinkled t-shirt with a hole in his sleeve—he’s rich and probably doesn’t care what people think). I felt like we “clicked” immediately and loved his sense of humor. He immediately asked me to tell him about myself, I could tell he liked the way we clicked when he started getting nervous, texting some friends (a couple who was in town) who were supposed to join us (I didn’t know that he invited his friends to our “date”).

They showed up ten minutes later; it was noisy at the bar and he mostly talked with the guy while I exchanged some words with the girl. It was impossible to get a one-on-one conversation that night. I was jetlagged from long travel, he had a long work day, and it seemed like we both got tired—maybe he got bored because I became really quiet. When we left the bar, he ran out the door with his friend, while the girl and I walked behind them. He asked me if I wanted to walk over to some other place but I was so exhausted that night, he hailed a cab for me. He kissed me on my cheek and said “Talk tomorrow.” I never heard back from him the next day, so I wrote him a “thank you” email. He just replied, “Let’s touch base later.”

I didn’t hear from him any more that weekend and had to leave town a day earlier. I informed him about it with two emails, he said he “didn’t see them,” while he was lying at some pool the whole weekend. I suggested we get together for drinks the night before I leave, he said, “He won’t be back before midnight.” I am over it, seriously. I texted him one more time, he replied that he looks foward to when I’m back in town. One person can’t do the work alone. I really like him for who he is, I don’t care if he has cash or can have every woman he wants to. I have my own career. However, we clicked and I’m confused and irritated. Not sure what to think … Please let me know your thoughts or some advice. Should I give him a second chance? I really like him.

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