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Banker's 1,615 word email to woman who didn't call him back.

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Hi Lauren,

Im disappointed in you. Im disappointed that I havent gotten a response to my voicemail and text messages.

FYI, I suggest that you keep in mind that emails sound more impersonal, harsher, and are easier to misinterpret than in-person or phone communication. After all, people cant see someones body language or tone of voice in an email. Im not trying to be harsh, patronizing, or insulting in this email. Im honest and direct by nature, and Im going to be that way in this email. By the way, I did a Google search, so thats how I came across your email.

I assume that you no longer want to go out with me. (If you do want to go out with me, then you should let me know.) I suggest that you make a sincere apology to me for giving me mixed signals. I feel led on by you.

Things that happened during our date include, but are not limited to, the following:

- You played with your hair a lot. A woman playing with her hair is a common sign of flirtation. You can even do a Google search on it. When a woman plays with her hair, she is preening. Ive never had a date where a woman played with her hair as much as you did. In addition, it didnt look like you were playing with your hair out of nervousness.

- We had lots of eye contact during our date. On a per-minute basis, Ive never had as much eye contact during a date as I did with you.

- You said, 'It was nice to meet you' at the end of our date. A woman could say this statement as a way to show that she isnt interested in seeing a man again or she could mean what she saidthat it was nice to meet you. The statement, by itself, is inconclusive.

- We had a nice conversation over dinner. I dont think Im being delusional in saying this statement.

In my opinion, leading someone on (i.e., giving mixed signals) is impolite and immature. Its bad to do that.

Normally, I would not be asking for information if a woman and I dont go out again after a first date. However, in our case, Im curious because I think our date went well and that there is a lot of potential for a serious relationship. Of course, its difficult to predict what would happen, but I think there is a lot of potential for a serious relationship developing between us one day (or least there was before your non-response to my voicemail and text messages).

I think we should go out on a second date. In my opinion, our first date was good enough to lead to a second date.

Why am I writing you? Well, hopefully, we will go out again. Even if we dont, I gain utility from expressing my thoughts to you. In addition, even if you dont want to go out again, I would like to get feedback as to why you wouldnt want to go again. Normally, I wouldnt ask a woman for this type of feedback after a first date, but this is an exception given I think we have a lot of potential.

If you dont want to go again, then apparently you didnt think our first date was good enough to lead to a second date. Dating or a relationship is not a Hollywood movie. Its good to keep that in mind. In general, I thought the date went well and was expecting that we would go out on a second date.

If youre not interested in going out again, then I would have preferred if you hadnt given those mixed signals. I feel led on. We have a number of things in common. Ill name a few things: First, weve both very intelligent. Second, we both like classical music so much that we go to classical music performances by ourselves. In fact, the number one interest that I would want to have in common with a woman with whom Im in a relationship is a liking of classical music. I wouldnt be seriously involved with a woman if she didnt like classical music. You said that youre planning to go the NY Philharmonic more often in the future. As I said, I go to the NY Philharmonic often. Youre very busy. It would be very convenient for you to date me because we have the same interests. We already go to classical music performances by ourselves. If we go to classical music performances together, it wouldnt take any significant additional time on your part. 

According to the internet, youre 33 or 32, so, at least from my point of view, were a good match in terms of age. I could name more things that we have in common, but Ill stop here. I dont understand why you apparently dont want to go out with me again. We have numerous things in common. I assume that you find me physically attractive. If you didnt find me physically attractive, then it would have been irrational for you to go out with me in the first place. After all, our first date was not a blind date. 

You already knew what I looked like before our date. Perhaps, youre unimpressed that I manage my familys investments and my own investments. Perhaps, you dont think I have a 'real' job. Well, Ive done very well as an investment manager. Ive made my parents several millions of dollars. Thats real money. Thats not monopoly money. In my opinion, if I make real money, its a real job. Donald Trumps children work for his company. Do they have 'real' jobs? I think so. George Soros sons help manage their family investments. Do they have 'real' jobs? I think so. 

In addition, Im both a right-brain and left-brain man, given that Im both an investment manager and a philosopher/writer. Thats a unique characteristic; most people arent like that. Ive never been as disappointed and sad about having difficulty about getting a second date as I am with you. Ive gone out with a lot of women in my life. (FYI, Im not a serial dater. Sometimes, Ive only gone out with a woman for one date.) People dont grow on trees. I hope you appreciate the potential we have.

Am I sensitive person? Sure, I am. I think its better to be sensitive than to be insensitive. There are too many impolite, insensitive people in the world.

I suggest that we continue to go out and see what happens. Needless to say, I find you less appealing now (given that you havent returned my messages) than I did at our first date. However, I would be willing to go out with you again. Im open minded and flexible and am willing to give you the benefit of the doubt. I wish you would give me the benefit of the doubt too. 

If you dont want to go out again, in my opinion, you would be making a big mistake, perhaps one of the biggest mistakes in your life. If you dont want to go out again, then you should have called to tell me so. Even sending a text message would have been better than nothing. In my opinion, not responding to my messages is impolite, immature, passive aggressive, and cowardly. I spent time, effort, and money meeting you for dinner. Getting back to me in response to my messages would have been a reasonable thing for you to do. In addition, you arrived about 30 minutes late for our date. Im sure you wouldnt like it if a man showed up thirty minutes late for a first date with you.

If youre concerned that you will hurt my feelings by providing specific information about why you dont want to go with me again, well, my feelings are already hurt. Im sad and disappointed about this situation. If you give information, at least I can understand the situation better. I might even learn something that is beneficial.

If you dont want to go out again, that I request that you call me and make a sincere apology for leading me on (i.e., giving me mixed signals). In my opinion, you shouldnt act that way toward a man and then not go out with him again. Its bad to play with your hair so much and make so much eye contact if youre not interested in going out with me again. I have tried to write this email well, but its not perfect. Again, Im not trying to be harsh, insulting, patronizing, etc. Im disappointed, sad, etc. 

I would like to talk to you on the phone. I hope you will call me back at xxx-xxx-xxxx (if its inconvenient for you to talk on the phone when you read this email, you can let me know via email that you are willing to talk on the phone and Ill call you). If you get my voicemail, you can a leave a message and I can call you back. Even if you dont want to go out again, I would appreciate it if you give me the courtesy of calling me and talking to me. Yes, you might say things that hurt me, but my feelings are already hurt. 

Sending me an email response (instead of talking on the phone) would better than no response at all, but I think it would be better to talk on the phone. Email communication has too much potential for misinterpretation, etc.




Best, Mike









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