To my socially awkward fellas: “Please don’t ask a girl out with an e-mail”

I’ve done this once before. Okay, twice. Okay, three times. Fine. It never turned out well and I’d like to tell you what I learned.

If you don’t read anything else below, I hope you will at least read this great article explaining how a easily an e-mail from an interested classmate can spiral into sexual harassment from a girl’s perspective:

Here’s my takeaway:

  1. It’s important to have a rapport with the person you like, before you ask them out.
  2. This is the hardest part. If they say they’re not interested and they just want to be friends, then you have to be okay with this and not overstep the friend zone.

P.S. – I’m writing this because I recently learned a coworker of mine tried asking a girl from our math department out via e-mail. It was really awk, and I wish I could have warned him about this first.

Here’s a more detailed breakdown of my own experiences.

First things first, for all three situations, I had briefly talked to these girls in person before (in math classes, haha). I had great conversations. And then I got it in my dumb head that it would be great to see this person again, maybe grab coffee, and maybe it wouldn’t be so bad to shoot them an e-mail asking if they’re free. I mean the worst they can do is say no, right? Wrong!

What happened for me is that the first girl flatly said no, the second girl stopped talking to me, and the third girl flatly said no as well.

I think the reason is that I didn’t have a good rapport with these girls I liked. In the first situation, there was a girl in my college Algebra class who I had only talked to in class. We always got along fine, but to this unsuspecting person, I was just some stranger with whom they had a couple nice conversations before class. She was completely unaware I was interested and I imagine that when I sent her an e-mail asking her out she felt rather blindsided. She stopped talking to me in class and I felt bad for making her feel so uncomfortable. In hindsight, it would have been better if I had just talked to her in person and if I focused more on just being a better friend to this person.

With the second girl I talked to, I made the worst mistake imaginable. I tried to “talk feelings” over a message. The NY Times article above explains this better, but long story short, I did my CS homework with this girl and over the semester, we became friends and I had a crush. I tried asking her out with a text and when she didn’t respond I just sent lengthy text after lengthy text expressing my feelings for her. Terrible. Utterly awful. We didn’t talk much after the course ended and we never did stay in touch. A word of advice. Please don’t hurl loaded emotions at another person. As much as you may want to “express your feelings”, no one enjoys receiving emotionally charged messages. Like how is anyone supposed to reply to those? This girl I liked didn’t want to reply at all. And in general it’s just not cool for friends to hurl heavy feelings at friends. In hindsight, after she didn’t reply to my first message asking her out, I should have backed off it and left her alone. I hope my experiences can be an abject lesson for you.

P.P.S. – Feel free to let me know you want me to update this with any further details about my unfortunate experiences. If it can help you, then my life is an open book.

Oh also, here’s an example of something corny that I once did to ask a person out to coffee. I really meant this one as more of a joke though: Screenshot from 2017-06-03 15:08:08

Update June 22: I forgot to mention that I’ve also had a couple girls before hit me out of the blue with an e-mail or text asking me out. I don’t judge them for it, but I’m telling you so that you know this can happen to guys too.






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