Men That Go Beyond One Email Attempt in Online Dating

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Recently I wrote an article discussing the topic of a man re-contacting a woman after his first email was unsuccessful (that is, she may have looked at his profile but didn’t respond).

In that article, I discussed how the reader had a theory that contacting later could be beneficial because she may be more able to respond at that time. This wasn’t something that I had considered in my original article on contacting a second time (but an idea I liked).

women's view on men repeatedly contacting them

In a sense, pursuit is something that we accept as common in the “old style” of dating. I’ve seen plenty of great relationships start because a guy wasn’t deterred by the fact that the woman rejected his first few attempts. I’ve seen friends remain persistent (while remaining respectful) and have success and long-term relationships/marriage.

So while it sounds like a good idea that a man would pursue a woman beyond one email, I’m looking to get some reader feedback from women on what they think of this approach. My concern is that what works well in the real world might just end up being creepy in the online world.

Some Questions for the Ladies

With that in mind, I’m curious if any women could comment on the following questions:

  1. Does the enjoyment of “being pursued” translate to online dating? Or are real life and online dating simply too different?

  2. If additional pursuit is acceptable, where do you draw the line for number of attempts? For example, the same guy emailing you every two weeks for a year, that would be annoying.
  3. Do you feel the man should wait an extended time before contacting you again? Obviously if he’s contacting you every day that’s bad but should he wait weeks to try again? Months? Never?
  4. Is there a point you would let the man know you’re not interested? Obviously no one expects women to respond to every email with “No Thanks” (and I’d honestly encourage you to not do that) but if a man were to contact you more than once would that encourage you to state that you’re not interested?
  5. Have you ever ended up dating a man that repeatedly pursued you online? If not, have you ever found yourself at least having conversations with them after a second email where you had not responded to their first email?

When answering those questions let’s assume:

  • He’s pleasant. He writes you real emails (not form emails) and may even make light of the fact that he’s contacting you again.

  • He’s within the requirements you describe in your profile. This doesn’t mean you find him attractive or interesting necessarily, but he’s not ignoring what you’ve stated that you’re looking for.

Obviously, every woman can be different in her views on this so I’m not really looking for a “right” answer for guys. I’m just looking for some honest feedback that guys could take into account as they try to pursue some women beyond a single email. I’ve been recommending that men be willing to make additional attempts and would be interested to see what women using online dating think of this.



About the Author:

Brad initially struggled with online dating but over time became quite successful using it. He met his wife using online dating and has been giving advice and helping people improve their results since 2007. He has written a Free Online Dating Guide to help others find success with online dating. You can learn more about his personal experience using online dating and running this website here.


  1. Melani  October 4, 2011

    Actually most of the men that we women ignored are the ones that are not pleasant nor do they fit our requirements, thus they are rightly ignored. And by unpleasant, I also include pics. There are lots of men with unpleasant pics on their profiles (ab pics, bathroom pics, making amateur insane expressions, tattoo or car pics, etc I could go on).

    Sometimes I view men with decent profiles and learn quickly that they smoke cigarettes and marijuana by reading their match questions, and immediately Im turnoff (No matter how great everything else is on their profile). It also seems to be case that 50% of men on okcupid smoke cigarettes and/or marijuana, already eliminating the large pool of men online.

    If we are assuming pleasant men as well as men who fit our requirement email us, of course they will get responses.

    1. I believe Yes for #1 because I am actually pleasantly surprise when a real potential match emails me (writes a good email, has a BA, etc). It can spark an immediate interest just like in person, even better because I am able to immediately know if this particular person has an education, a job, intelligence by reading their profiles.

    2. & 3. An acceptable second email attempt I think should be sent after two weeks of the first initial one. But if she doesnt respond, I wholeheartedly believe the guy should move on. You deserve better if she is pretending your emails do not exist.

    4. To be fair, women show disinterest by not responding. Jerry Seinfeld once said “men are obvious, women are subtle.” I cant agree more….Women are subtly saying “Hey Im not interested” when they dont respond. I know I am, I am not very comfortable emailing someone I dont know very well in an email turning them down. Im assuming most women are the same, as it seems this is universal. Especially if you sent a second or third email, if she doesnt respond, look elsewhere. Most likely she is not interested, especially if you see her online all the time. She got the email, she is just not interested.

    5. No, but Yes I did find myself responding to guy after a second email to see where it would lead…and usually it lead nowhere.

  2. Liz  November 25, 2011

    In the time that I’ve been dating online, I haven’t experienced the situation where a man persisted beyond one email. When I get an email from someone who does not seem like a good match, I either ignore or reply with a polite “No thanks”, so it never goes beyond that point.

    Whether I’d welcome a second attempt depends on my initial impressions of the guy based on his profile and the style/content of his initial email. For instance, was it a bland, form-style message? Or was it a sincere, personalized message that shows he obviously read my profile? In the latter case, (assuming the man fit my criteria), I would be open to a second attempt (if for some reason I hadn’t yet responded to his first email). If the initial email was not even a pleasant, individualized message but simply a form-letter, I would be annoyed by a second attempt (*unless* for some reason the guy was smart enough to pull a save by crafting a genuine, personalized email the second time around). 🙂

    If a guy wanted to send a follow-up message to a woman who didn’t respond to the first email, I would say to do it within a couple weeks, as the previous poster (Melani) suggested. Too soon (within a day or two) could be creepy and annoying…too late (beyond a month or more) just doesn’t seem right either.

    As for me, If I’m truly not interested, I usually send a polite “no thanks” early on, that way there’s no mystery about whether I even received his email, or whether I haven’t replied because I’m busy, or whatever. I may be in the minority, but I also prefer to hear a “no thanks” response from a guy who may not be interested in communicating with me (if I was the one to initiate communication). At least I know he got my message and he’s not interested, so there’s no reason to send a repeat message for any reason … I can simply move on without wondering.

    I do have to admit though, there was this one time a guy was VERY detailed about why he wasn’t interested in me in particular — wow, that really STUNG. In that instance, I wish he would have simply ignored my email or made up a white lie about having met someone else. 😛 Hm, in checking the dating site now, it appears he’s still “available”. Maybe I should try a second attempt at contacting him? NOT. 😛

    • Exagerado  September 13, 2016

      @Liz: “As for me, If I’m truly not interested, I usually send a polite “no thanks” early on, that way there’s no mystery about whether I even received his email, or whether I haven’t replied because I’m busy,”

      Thank you Liz,

      It’s amazing how rude we can be. Ignoring someone who send us a thoughtful email?

      (In the case of a nasty email, one can always block him/her.)

      Politeness doesn’t hurt. It should always be like that (sorry Brad to disagree with you on this) so there is no wondering.

      @Melani “men are obvious, women are subtle.”

      You think? Amazing how some people buy into these old clichés… *some* men are obvious; *some* women are subtle. That’s what Jerry should have said, would he knew a thing or two about genders.

    • Exagerado  September 13, 2016

      @Liz “I do have to admit though, there was this one time a guy was VERY detailed about why he wasn’t interested in me in particular”

      There’s a guy with no class.

      I’ve turned many women down (sorry, I’m picky) but I never detailed or even pinpointed the reason, even when asked. I will just say something the lines of “I’m not feeling it” or “I don’t see a match here” always followed by “(mea culpa, sorry)”.

      Saying something like “sorry, I’m not interested in someone that smokes” (which is true) would appear reductive and judgemental. I am no better than you; just different, would be my motto.

      P.S: I forgot to say, I never contacted a woman twice. I always imagined that if a woman doesn’t respond to my thoughtful personal email it is because she isn’t interested. Even if she is busy and/or pursuing a potential serious relationship; I would think that it wouldn’t hurt to say something along the lines “hey, appreciate your email, but kinda busy right now, sorry”. That would give me the hint and maybe within a month I would reach them back. Just saying. I don’t see anything good arising from the silent treatment. With all due respect, it strikes me as plain selfishness and an ego-centered mind, which I run away from.

      Thank you Brad and all the ladies who commented.

    • Sterling  February 20, 2017

      thanks. I wish more women were like you. a polite “no thanks” is very cool and non-judgemental and yet, quite direct…which I (and I think most men) like.

      It lets me know that you’ve received the email, read it, checked my profile and are not interested…no muss, no fuss, no worry…helpful for us “obvious” guys 🙂

  3. Naomi  April 15, 2012

    I’ve had a few situations where I’ve had repeat emails – more often than not they are from men who clearly don’t remember they’ve already contacted me, and are sending the same spam email again. In this situation I would just block them, they really don’t deserve any consideration!

    However, if a man sent me a genuine email for a second time, I would most likely respond, even if just to tell him I’m not interested. I wouldn’t mind him contacting me a second time (and I agree with previous responses – one to two weeks is a good length of time), mainly because I get a lot of emails, so it is probably easy for me to miss someone. However, if I don’t respond after two attempts I wouldn’t really want a third email – you’re right, this is bordering on stalking!

    I have ended up having conversations where I have ignored the first email, I’ve probably even had dates from this, but I don’t think I’ve dated anyone for any period of time. However, I think most women like being complimented, and chased to a certain degree, so as long as this is done in a respectful way, I can’t see a problem.

    I think a bigger problem is the lack of decent first emails from men – possibly less than 5% of emails that I receive make me want to reply. The main problems are lack of anything in them that I can respond to (e.g.” hey, how’s it going?”, and nothing else!), lack of respect (“hey sexy, love your pics!”), or the fact that it is very obviously a generic email. I think if men just put a little more effort in, they would get many more responses! Men often write to me saying it’s nice to see a genuine profile from someone who knows what they want – well, it’s nice to see a genuine email as well!

  4. DazlingDater  April 19, 2012

    When I first signed up for Match I was overwhelmed with emails. A lot were just “Hi” or “really like your photo.” It was difficult and time consuming to weed through the emails looking for a possibility and I’m sure I deleted one or two that deserved another chance. If you are similar in appearance to that person; i.e., weight proportion, attractiveness, social circles; I would recommend responding again after four days or a week. Follow up with a pleasant email that addresses something specific about that person’s profile and be sure to ask a friendly question other than “want to meet?” If they don’t respond a second time they probably don’t feel you are a good match. Don’t take it personally.
    I actually met a man for lunch and agreed to meet him again but cancelled because I felt he was moving too fast. He texted me after about a week and asked if we could meet again, and I agreed. It turned out I liked him very much and we enjoyed our time together while it lasted.
    If you like a person, always include a question in your email to engage them to answer back. If you simply answer their email with a statement, it places a burden on them of pursuing you or they may think it’s your way of backing off.

  5. Brad  April 20, 2012

    Thanks for the feedback everyone. It’s great for us guys to hear feedback from what women are seeing/dealing with. Really appreciated.

  6. Nigel  November 23, 2017

    I have contacted people twice sometimes. I usually assume a no response is a lack of interest and move one. However I have seen profiles where I think we are particularly suited, and maybe we live quite close, so I think it is worth a second shot. I would wait a couple of weeks. I would acknowledge that it is my second email and I would say why I am emailing again. I’d also keep the second email quite short. I did this once with a woman whom I had contacted when I first started online dating and who I thought was particularly compatible with me. I hadn’t read the rules so I had sent her a long email 🙂 I had no reply. A few weeks later I tried again and this time she did respond. She had just been busy and hadn’t used the site much. I got lucky the second time. We chatted and met up. We had three dates. It went no where but still…


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