1,615 word email: Here’s how NOT to get a second date

It started off simple enough — two kindred souls finding each other amongst the romantic melodies of the Philharmonic. At least, that’s how it seemed for Mike, an investment banker who met Lauren when they both attended a concert solo. Lauren, however, was on her own because her friend got sick at the last minute. Mike was on his own…. well, for reasons that will become obvious shortly.

Dating in NYC can be a total freak show, but the 1,615 word email that Mike sent Lauren after their first date (he Google-stalked her email address) is the stuff of nightmares. She posted his message to Reddit after getting fed up with numerous calls and texts from Mike following what she called a “horrific” first date.  

In his quest for truth over what happened between them to discourage her from wanting to see him again, he reveals his countless insecurities from whether he is physically attractive to the fact that managing his parents investments should surely be considered a “real” job.

Reading the whole thing is a real treat. It’s long, but you need to take it all in to get a true picture of the insanity.

Here is Mike’s full email to Lauren — all 1,615 words of it:

Normally, I would not be asking for information if a woman and I don’t go out again after a first date. However, in our case, I’m curious because I think our date went well and that there is a lot of potential for a serious relationship. Of course, it’s 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 don’t, I gain utility from expressing my thoughts to you. In addition, even if you don’t want to go out again, I would like to get feedback as to why you wouldn’t want to go again. Normally, I wouldn’t 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 don’t want to go again, then apparently you didn’t think our first date was good enough to lead to a second date. Dating or a relationship is not a Hollywood movie. It’s 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 you’re not interested in going out again, then I would have preferred if you hadn’t given those mixed signals. I feel led on. We have a number of things in common. I’ll name a few things: First, we’ve 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 I’m in a relationship is a liking of classical music. I wouldn’t be seriously involved with a woman if she didn’t like classical music. You said that you’re planning to go the NY Philharmonic more often in the future. As I said, I go to the NY Philharmonic often. You’re 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 wouldn’t take any significant additional time on your part.

According to the internet, you’re 33 or 32, so, at least from my point of view, we’re a good match in terms of age. I could name more things that we have in common, but I’ll stop here. I don’t understand why you apparently don’t want to go out with me again. We have numerous things in common. I assume that you find me physically attractive. If you didn’t 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, you’re unimpressed that I manage my family’s investments and my own investments. Perhaps, you don’t think I have a ‘real’ job. Well, I’ve done very well as an investment manager. I’ve made my parents several millions of dollars. That’s real money. That’s not monopoly money. In my opinion, if I make real money, it’s a real job. Donald Trump’s 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, I’m both a right-brain and left-brain man, given that I’m both an investment manager and a philosopher/writer. That’s a unique characteristic; most people aren’t like that. I’ve never been as disappointed and sad about having difficulty about getting a second date as I am with you. I’ve gone out with a lot of women in my life. (FYI, I’m not a serial dater. Sometimes, I’ve only gone out with a woman for one date.) People don’t grow on trees. I hope you appreciate the potential we have.

Am I sensitive person? Sure, I am. I think it’s 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 haven’t returned my messages) than I did at our first date. However, I would be willing to go out with you again. I’m 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 don’t 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 don’t 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. I’m sure you wouldn’t like it if a man showed up thirty minutes late for a first date with you.

If you’re concerned that you will hurt my feelings by providing specific information about why you don’t want to go with me again, well, my feelings are already hurt. I’m 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 don’t 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 shouldn’t act that way toward a man and then not go out with him again. It’s bad to play with your hair so much and make so much eye contact if you’re not interested in going out with me again. I have tried to write this email well, but it’s not perfect. Again, I’m not trying to be harsh, insulting, patronizing, etc. I’m 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 it’s 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 I’ll call you). If you get my voicemail, you can a leave a message and I can call you back. Even if you don’t 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

So, do you think Mike should stop playing hard to get?



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