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I'm attempting to meet somebody on a few dating websites. The sites that I'm using all rely on internal messaging systems and user-created profiles to stimulate conversation, so the only thing I know about other people is their pre-written descriptions. Favorite books, movies, basic physical attributes, and freeformed About Me sections. As a man seeking a woman, statistically I'm the one that has to make the first move and introduce myself.

Problem is, I have no idea what a good introduction is. I've tried some variants of "Oh, cool, you're a fan of X? So am I! What's your favorite episode of X?" with common hobbies and I've asked for details on hobbies or jobs, but so far these messages have been opened but have not received replies. According to all of the internal algorithms I'm contacting people that should be good matches, so I don't think it's a lack of commonality. I'm coming to the conclusion that I'm just bad at striking up a conversation.

What is a good way to start a conversation on a dating website?

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I'm Catija. I'm female and I met my (male) spouse on one of these dating sites. We met about 11 years ago and this is what made me respond to his message... and what made me not respond to others.


First off, when I joined said dating site, it was because I wanted to take the quizzes. Yeah, I know that everyone claims that, but it's actually true. My profile is pretty brutal. The "you should message me if" part of my profile reads:

You enjoy failure... You did read the bit at the beginning about not talking to strangers, right?

I also wrote all sorts of off-putting rules:

Profile page excerpt. Text reads: I hate being objectified. Calling me "babe" or "sexy" when you've never met me will lose you too many points, which you'll never get back, not that you'd get the chance. Do not order me around. I don't know you. If I chose to ignore you, suck it up and move on.If you REALLY want me to talk to you, say something interesting. If you just say "Hi" or "How's Austin?" you will be ignored. I am going to clarify this because a lot of people don't seem to "get" it: If you send me an IM and all it says is something boring, like the previously mentioned statements, you will be ignored and I will NOT even open the IM window! Yeah, maybe you'd say I'm a picky girl (although you might use a different adjective/noun combination) but I just like to put things out front to weed out people before I get too many messages.Oh, one last thing, the

Yet, through all that, my dearest Andy still decided to message me. And I'm glad of it.

As a female who has used a dating site successfully, this really is what you have to put up with so, thank you, thank you, thank you for asking this question. I really hope that you can get some great recommendations from the users here.


Show some respect I'm sorry, but I'm going to get this out of the way first because it's gross (to me) and I really think that some guys out there don't get it but... Don't proposition someone with sex... of any kind unless they somehow make it obvious that they're interested in that sort of thing. If they have the "hookup" or "one night stand" or other setting turned on or they mention it in their profile.

Focus on their personality. Realize that not every woman wants to be greeted with "hello sexy" or "hello pretty" (yes, I've gotten both and more) or even have anyone mention their looks at all. I personally find it creepy. Do you want someone telling you that you're a big hunk of handsome as the only greeting you get? There's a difference between saying (as part of a longer message) something like "I see we're a really strong match and I also find you very attractive." Is more welcome than "Hey, hottie, wanna get together?"

Show them that you're really interested in them. You're trying to find someone to date, to get to know better... Put some time into your communication with them. Find someone who's a good match for you and really read their profile. They wrote it for a reason... they want you to read it. Show them that you did by writing a nice 2-3 paragraph introduction that tells them about you (so they don't have to look at your profile) why you're contacting them (shows them that you've read theirs) and asks questions that draw them in (people like answering questions).

I wish I still had the message Andy sent me. While I have some of the later ones, the original one somehow got deleted. It did all of the things I list here. He introduced himself generally and told me things about himself that matched up with things I mentioned on my profile, he explained why he was contacting me despite my many warnings not to do so, and he asked me questions I wanted to answer... and I did.


Let's do a little case study:

As you say in your question, women get lots of messages. I haven't been active on the site until today because I'm happily married but even now I have messages waiting for me, all from May... for some reason... let's talk about them.

  1. A message from someone with a username implying that they're in Austin but their location is in India asking for a one-night make-out session, possibly in public. I'm not going to post this one because... Ewww. It's not actually as graphic as some of the ones I've gotten but the location isn't uncommon... lots of people from India contacting me in America.

  2. A message from someone in Hutto, TX (near Austin) that just says "Hello".

  3. A message from a guy named John in Austin who only talks about himself - probably a form message he sends to everyone he reaches out to.

Hi there! My name is John, pleased to e-meet ya! I have to be honest, I never really know how to fill up these types of first-contact messages. I'm not one to send a msg and be all forward and say "i wanna do this or that to your buttcheeks," etc. Plus, it's not exactly the definition of polite. So there ya go.

So a little about me, I suppose? I'm 39, pansexual and have a good sense of humor. I play music. I play a bit of bass guitar, standard guitar, and I am also a drummer. I'm no professional, but I can keep a beat.

Um, I'm not sure of what else you'd like to know, but I'm sort of an open book, so feel free to ask!

Hope to hear back.

John

This doesn't show that he read my profile but it's funny, open, long but not too long. I like that he makes fun of the people I talk about in the first point without being overly graphic because it shows that he understands what a lot of ladies go through. This has a better chance of getting a response (from me) than most other messages.

  1. Someone who no longer has an account making negative commentary about my profile

You don't talk to strangers? How do you expect to make any new friends with that attitude? It's, like, everyone's a stranger until you give them a chance. Hope you know where that came from and are having a good night.

Not much to respond to here... not sure why they even messaged me. I do get a lot of these, though... people arguing with my profile, as if I'm required to want their attention. Oh well... moving on.

  1. Another person who closed their account but felt like telling me how much they like Cowboy Bebop.

cowboy bebop kicks ass, the non dubbed version

This refers to something I mention on my profile, so at least he read it. Still wouldn't get a response from me.


So, in the end, endeavor to be like John but add a bit more that's referential to the woman you're contacting. I don't know how many women you're planning to write to but take your time. Those usernames are actually people (probably)... treat them like it. Think about what you talk about when you meet someone at a party. Go from there.

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    I appreciate this doesn't mean much, but I am so so so freaking sorry you have to put up with that. It screws up the entire system and I can't stand I'm sharing the same pool as some of these guys. – GGMG Aug 30 '17 at 3:29
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    But... what is that "last thing" missing in the image? – Daniel Aug 30 '17 at 13:47
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    @Daniel an explanation of how to parse my username on the site. Excluded for that reason. – Catija Aug 30 '17 at 13:51
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An entire book could be written on this subject, so I don't know how on target it is for his site (possibly "too broad") and there are thousands of variables/no "one size fits all" approach but:

Consider that women will receive somewhere between ten to a hundred times more messages on dating sites for every one message that a man gets as a conversation start. There's an incredible amount of noise in the typical female inbox, and scores of messages from absolute idiots who spam the same thing out to hundreds of girls in one sitting. It is incredibly tedious for most girls just going through their inboxes and deleting all the chaff.. Any message you write will have to stand out from the others and give the recipient an indication that you're going to be fun to converse with.

Reading their profile is good, establishing some common interest is useful also, but maybe don't immediately jump to asking a question because it's hard to ask a good open question worthy of a debate grade answer that is worded in a way that paints a picture of you as being worthy of receiving that answer. Confused? I'll try and simplify it.. A good question needs to generate an answer longer than the question, that introduces new info that can branch a conversation out. The question also has to be worded in such a way that it's different, and hence indicates you're different, or the way you think is different, and piques their interest. This is really hard to do with the small number of words your question needs to be in order to get to the point. "I see you like green day too. What's your favourite song of theirs?" - meh, it's too closed, too easy to answer, too limited in its scope for introducing new info, too likely to generate disagreement with the answer and a little too predictable - might even get asked 10, 20 times a day if green day is about the only well known or stand out thing about her profile..

I always found better responses if I could put together a short message that told a bit of a funny story, or jokingly started some point of debate, 5 to 8 lines, maybe a question at the end (but if the message was contentious enough that she felt she had to respond to put me right, or sound off in agreement it doesn't always need a question). Something that is indicative of your sense of humour is vital. Getting the length right is important. Too short or scant on personally relatable information, and you're in the bin as a copy paste chancer. Too long and you're in the bin as a too intense psycho who's picked the names of your+her unborn children already. Pick on a subject that few people will have asked about or noticed, something between the lines in the profile or in the background of a posted photo. If there isn't anything, and her profile is dull as dishwater or worse "I can't be bothered to write a profile, any questions just ask me" - don't bother; this girl is not putting the effort in regardless of how pretty her cover pic is. When writing messages, if you're not in a good, happy, confident, "a girlfriend is the last thing I need" mood, consider doing something else instead.. like going for a run. It's so easy for your mood to enter these "short but sufficiently revealing" mails, and if you're desperate and lonely it will be incredibly hard to hide it and it's a massive turn off. Finally, never, ever copy a message to a previous girl and paste it back in with a couple of words changed to "personalise" it for "another her"

Put a reasonable amount of detail in your own profile; it's highly likely she will read it before deciding to respond. Put YOU in your profile. Write how you speak; several people over the time read my profiles and were pleasantly surprised at the way it was writtten and how it turned out to be a reflection of the way I thought and spoke in terms of style, word choice and tone. Some of my profiles were written as if it was a conversation I was having with the dating site, or the girl reading the profile. None of it was "oh. Umm. I have no idea what to put here. Just hit me up if you have any questions" - if I didn't like the question the site asked, I found an excuse to change it to one I wanted to answer

At the end of a session, look to have sent about ten mails to new people and then forget you ever messaged any of them (well, apart from maintaining enough of a memory that you don't message them again). Forget how much more perfect than all the others she was, forget the vows you'd write for her.. Until a mail from her lands in your inbox, she's not on the radar. This will help prevent you getting into a warped sense of perspective about this person whom you actually know very little about. If the response doesn't land, then take some comfort in the fact that women are much much better at assessing compatibility than men.. if you're not getting a response, your approach is causing her to filter you out. If your approach is absolutely and naturally a great representation of the person you are, she's filtering you as no-match. If this keeps happening, you may be selecting the wrong candidates to assess you. You can tweak your approach a little, but keep it true to you to avoid problems later on. Some of the sites popular these days have their own forums and you can ask for profile reviews. It my also help to engage a friend who knows you well, to see if their perspective on your profile and the sorts of messages you're sending is an accurate depiction of you

Final tidbit, if you persevere and enjoy only limited success, do a bit more research; create a female profile, using some photos of a friend (with their permission, of course) who is of similar physical appearance to the sorts of girls you're approaching, write a generic profile for the details (it doesn't matter, men don't read much) that is a similar kind of girl as what you seek and then just wait and see that absolute torrent of shite that lands in her inbox. This is what you have to beat in order to stand out. It will probably surprise you just how much crap the poor girls out there have to wade brought and probably explain why most of them get tired of it pretty quickly and log off forever, or become incredibly discerning (and by that I mean, she takes a week long holiday to Spain, comes back to 500 "hey u hot" messages, with your diamond effort in the middle, and just hits Ctrl-A followed by Del.. luck of the draw, and a reason why I said to put no one on the radar/"favourite profiles to stalk list", until they write back..

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    I'd love to +1 this, but I strongly object to your suggestion to create a fake woman profile to prove a point. This system is already a messy trust exercise for all parties, I don't want to encourage more dishonesty just for personal satisfaction. – GGMG Aug 30 '17 at 1:08
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    This is not for your personal satisfaction. It's for your learning if you're still not getting it after X months; you're smart and can certainly craft it in such a way that you're not going to be leading any forlorn hearts astray, you're not going to be getting into a conversation with these people (nowhere did I advocate responding) and youll very rapidly come to understand things from your target audience's perspective. Taking personal objection to something written in an answer is not adequate reason to vote down, see stackoverflow.com/help/privileges/vote-down, welcome to SE – Caius Jard Aug 30 '17 at 1:30
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    @CaiusJard If no-one downvoted due to personal objection, nothing on this specific site would ever get downvoted, because that's the only / main reason why you'd downvote here. Nothing in that link dissuades doing so and the "official" stance on when you're "allowed" to downvote is fairly easy-going, as long as you're voting on content and not targeting users. OP also said they didn't want to upvote, which is not the same as downvoting. – NotThatGuy Aug 30 '17 at 10:23
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    "the fact that women are much much better at assessing compatibility than men" - seems a bit over ambitious and generalised.. adding a source or personal experience to explain might help – Jesse Dec 8 '17 at 6:30
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Remember that "how to start a conversation" is not always about the message you'll sent her.

If a stranger send me an introduction and wish to know about me more, this is what I will do, in order:

  1. Glance on the message.
    First of all, be polite. Joke is great, as long as it is funny. I will not cover much about the message because other answers usually will address this.
  2. Check profile picture. Anything other than their picture (or animal) will surely get my attention. On ignore button.
  3. Check their About Me section.
    Everyone will sell their attractiveness. I'll make sure this one does not oversell themselves. Of course, empty or uninteresting section will also get a big NO.
    Some people like long, descriptive About Me. People like me prefer shorter advertising. It's up to you, but try to limit a paragraph to 3-8 lines max.
  4. Optionally, when 1-3 pass and when I feel like it, I will check their other social media, if I can find it.
    If you can confirm it's the same person, conflicting description is a huge red flag.

Of course, everything is up to what your goal on joining the dating site.
Dating partner? Girlfriend? Marriage?

More casual profile pic and description will attract the earlier, while someone looking for serious relationship will check for signs of maturity. It's your call.

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You need to "declare yourself" at the beginning. Give the essence of who you are in one or two short sentences, to encourage the few that you want, and discourage others. My own approach to date selection might have been summed up by "the few, the proud, the Marines." OK, maybe not "military" women, but rather "special forces."

One example of such a declaration (not even in a dating context) is, "We respect a laser-like focus on one topic." That describes a no-nonsense individual, who will discourage "scattered" women. If that's you, you will attract dates who will get right to the point.

A declaration that's similar in quality, if different in content, is "I love children and small, cuddly animals." That will attract a different sort of date, one that's compatible with that type of individual.

Whatever you post, make it short, make it memorable, and above all, make it you.

  • Who is the "we" in "we respect a..."? – Kat Sep 5 '17 at 20:37
  • @Kat: I was quoting someone's "tag line" from a non-dating site. For the purposes of illustrating clarity of expression. – Tom Au Sep 6 '17 at 0:32

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