Burning Question: Can I Email Someone Twice?

This, but with boobs.

I think that, honestly, the woman of my dreams probably doesn’t email people back right away. Certainly not the people she encounters online dating. First of all, she’s busy. She has a demanding career in the field of writing for SNL/teaching literature/impersonating Jessica Biel/being the first female manager of the Boston Red Sox. On top of that, she has her hobbies. And frankly, the girl of my dreams just doesn’t feel right if she can’t spend at least an hour a day parasailing/playing guitar/cleaning up oil spills/training to be the first female manager of the Boston Red Sox. So I understand if she doesn’t respond to my first email quickly, she probably gets so many. It’ll take her a day or two to wade through the other suitors and come upon the majesty of my message. She will open it and immediately see that this is the one. She’ll recognize it for its humor, its intelligence, its obvious demonstration of an almost supernatural sexual appeal. But what if, even then, after she’s saved the rainforests and adopted all the stray puppies and called for the perfect hit and run, what if the girl of my dreams still doesn’t write me back? What do I do then?

Simple. I write her again.

Hold on! What?! You can’t write someone twice! You’re harassing them. You’re becoming one of those deranged Internet daters who copy and paste every message, who live in a different state, who have only the loosest understandings of the English language, who never ever ever take “no” for an answer. That’s what people say to me when they ask if they can email someone twice. Then, calmly, sagaciously, in a manner that no doubt reflects the great Dalai Lama himself, I respond, “What’s the worst thing that could happen? She’s gonna not write you back…again?”

Wanna know what the perfect second email should contain? Of course you do. Well, all those precious details can be yours for JUST $2.99! 

Buy my new book Not a Match: My True Tales of Online Dating Disasters. Available for your ereader on Amazon and iTunes. I promise it will get you laid! (May not be true.)

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14 Responses to Burning Question: Can I Email Someone Twice?

  1. J says:

    What if the second email is all,

    “Why haven’t you written me back? I want to write you love poems. Badly.”


    Because when I got that one a few years back, I considered changing my locks.

    • Marco Esposito says:

      Not crazy… really crazy people. ?.. I’ve been sending multiples all along. Sometimes I “rain ” with single word emails just to take up space in the inbox.

      Still well intended and working the site happily and sometimes not so much. It’s like life and the box of chocolates ya know.

  2. J says:

    …And / or laughing at the idea of love poems.

  3. luckyemail says:

    Dude, did you hack my email and read the first few messages I sent my gf? She wrote me back after the first two, then went on vacation and I didn’t hear from her for 10 days. Imagine if the girl of your dreams won’t respond for 10 days after two charming, chemistry-ridden emails. It drove me crazy. Cut to the end: I emailed her, she emailed me back, we met, she fell madly in love with me the moment she saw me, and now she’s begging me to stop writing so we can pick out the names for the kids we don’t yet have. Lesson? send one more email than you really want.

    • B says:

      That’s a good rule. When dealing with people you’ve never met, and won’t meet unless they respond, one more email is never a bad idea.

      And yes, I did hack your email. You should write your Mom back, she misses you, for God sakes.

  4. Phil says:

    A similar situation happened to me. However it is a bit different.
    The last time my ‘gf’ wrote to me was in April this yr. I was quite certain that she still loved me at that time. Then she returned overseas back to her home.

    One month later in May, I sent her a message asking abour her current situation but she did not respond. After waiting for another month in June, I wrote to her through email asking a similar question but there was still no response.
    (I am unable to contact her through cellphone because she is in an overseas country and the dialing codes don’t work at all. I tried to add her to my contacts through skype but there was no response.)

    I really don’t know what to do now. Should I message her a third time? How should I carefully word it so that she would eventually respond to me? If I choose to remain silent from now on until she replies, is this a good or bad idea? I would like to hear perspectives from both genders regarding the possible explanations as to why she is doing this and the best course of action that they would take if they encountered this.

  5. theshoegazer says:

    I’ve probably emailed someone twice… by accident. When I do online dating, I rarely stay on whatever site I’m on very long. I hang around long enough to search through most of the compatible ladies in my area and send out a few emails. Once my searches just return the same people over and over again, I quit and try a different site or cool it for awhile. And then if I return again 8 months later with a new screen name, I’ve been known to email a girl, forgetting that I’d written her before and she didn’t respond.

    On the flipside, I had a girl email me 5 or 6 different times via craigslist several years ago. Yeah, I know, posting on craigslist… but I actually met a very normal girl there once who I wound up dating for almost 3 years. Way more wackos than girlfriend material though, and once I even got an email from weirdo girl after writing “please no serial internet daters or frequent CL users”.

  6. NunyaBiz says:

    Great article, but I have a fairly different spin on the situation plaguing me right now. I’m trying to be friends with a woman that has already slept with me, early on in our friendship. We were not in love, we were just having fun – I am in a poly relationship with another woman. We had to stop on account of her finding a new, monogamous boyfriend. I was dismayed by this at first, given how suddenly our sexual relationship began and subsequently ended, and I let her know. However, I also let her know that I would support her wishes. She said we could still be friends, and I thought everything was cool. I got over it in just a day or two, and I only want to continue being friends, like SHE suggested we could! That was a little while ago, and the last message I sent her was about three weeks ago. I’ve yet to hear from her in any form or fashion, and it’s really worrying me. I’m hoping she didn’t misinterpret my intentions as crazed, desperate, or the like. The thing is, I will most likely see her at an upcoming social event out of town, and I’d rather it be as friends than awkward acquaintances. What do I do?

    • B says:

      Well, it sounds like she either doesn’t really want to be friends, or can’t handle it with the complications that have arisen. I’d just let it go for now. If you run into her later you’ll have a better chance to rekindle your friendship if you haven’t hassled too much over the past. And truthfully, how likely is a great friendship to come out of these circumstances anyway? I wouldn’t worry about it, and let it be whatever it is…

  7. K says:

    Dude erase this page, before anyone else reads it! LOL Great tip man!

  8. Pingback: Advice From a Hot Chick: How To Email Your Dream Girl | It's Not a Match.com

  9. “Not a Match…” is a great book! I want to endorse the books formula for initial emails and follow-up emails. I also feel much better about me dating disasters having read B’s tales.

    You will laugh your ass of in the process….but I can vouch that the book does give sound advice on the follow-up email subject. And if you don’t believe B, read the “Advice from a Hot Chick” link above.

  10. Pingback: It’s Illegal To Lie In Your Dating Profile | It's Not a Match.com

  11. chaddie says:

    When someone says “let’s just be friends”, they never, EVER mean it. They’re only saying it to assuage their guilt over ending a relationship, regardless of the relationship type.

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