Help me write excellent online dating emails.
October 20, 2008 10:11 AM   Subscribe

I'm not a bad writer, but I'm really, really bad at writing online dating emails. Please give me some tips on how to write an excellent online dating email.

I keep finding myself in the situation where a girl likes my profile and sends me an email, but after I respond, I never hear back. Obviously, I know how to write a compelling profile, otherwise she wouldn't be writing to me in the first place. However, I always manage to screw up the email.

I'm not a bad writer. In fact, I've been complimented on my writing by many people. However, there's something about the online dating email that just eludes me. Perhaps my tone is too formal, or maybe my emails are too long. Who knows. In any case, the result is often the same - a big, fat, unresponded email.

And so I turn to you, hive mind.

Girls - what do you look for in an online dating email? What makes you think "this guy is someone I would like to meet?" What are some specific turn-offs? How many questions should I ask in an email? How long should an email be? How can I avoid looking desperate? I promise you that I'm not actually desperate.

Guys - what works? What doesn't work? (and by "work," I mean "get a positive response that continues the conversation.")

I don't write crude, risque, or profane things in my emails. I write complete sentences and use correct spelling. I capitalize properly, and I don't use chatspeak. So no need to remind me of any of these things.

Thanks for the help.
posted by Sloop John B to Human Relations (43 answers total) 21 users marked this as a favorite
Dude, I'm a woman and I'm having the same problem; it may actually not be writing so much as "bad luck".

But I'd be interested in having you send me a sample email through Mefi mail and I can give a more direct commentary, if you're interested. (Shoot, maybe we could swap emails and give feedback to each other.)
posted by EmpressCallipygos at 10:23 AM on October 20, 2008 [1 favorite]

In my experience, you should be concise, casual, and honest, and if she doesn't reply, try not to worry about it. People are weird and flaky, it's probably got little to do with your writing style. Being witty is good, but you don't want to force it. Don't go for overt compliments.
posted by ludwig_van at 10:31 AM on October 20, 2008

For a first email, I'd say you want to be encouraging, but not overdo it. Your email should ideally be slightly longer than her initial email -- you're continuing the conversation and showing interest, but not immediately launching into pages and pages. The length of her email should give you a clue about how much you should write.

As for what to talk about: Thank her for getting in touch. If she has any questions, answer them. Pose one or two questions of your own. Mention what you like about her profile. That should do it, I would think -- you won't always get a response, but if you stick to that, I don't think you'll turn her off in any way.

Is there a photo in your profile? If not, does she ask you for a photo in that first email message? If you're reluctant to provide one, she may see that as a red flag. If you do send one, ask a friend to take a look to make sure it's a decent shot. (It's hard to be objective about your own picture.)

Out of curiosity, if YOU write the first email, do you usually get a response?
posted by cider at 10:34 AM on October 20, 2008

First, and it might be me, but I haaaaaate being called a girl. I'm an adult woman. With that out of the way, you might very well be right about the emails being too long and/or too formal -- I get that feeling from the way your question here is posed.

When people are reading online, they expect short paragraphs and an easy read. When I was doing professional web writing, the rule was to limit paragraphs to three or four sentences. I would think three paragraphs should be enough to get across what you're trying to say.

Another thing to remember is to ask questions, or give the woman something to respond to; I think we've all gotten emails that leave no room for response, where it's clear that the author has entirely forgotten that this is to be a kind of conversation. Be funny if you can. Don't be funny if you can't, or if you can't do it well via email. Don't brag too much.
posted by runningwithscissors at 10:37 AM on October 20, 2008 [3 favorites]

Without concrete examples, it's going to be hard to give you concrete pointers, but:

Perhaps my tone is too formal, or maybe my emails are too long.

If you have to wonder about these things, the answers are probably yes and yes.

But! I've had my share of online dating email correspondence, and most of them do fizzle out even when they start out promisingly. In general, you're likely fine, and it's just the luck of the draw. Think of it more as a casual conversation than a cover letter.

One thing that almost always helps is asking a question near the end of the email, or introducing a new subject, or anything that can push the conversation forward or in a different direction. There have been times where I've not responded to emails because I just couldn't think of anything to talk about. (If you ask about something in her profile, don't ask about the most attention-getting thing, because that's what everyone else is asking about. Talk about the one obscure film buried deep in her likes and dislikes, instead of the Most Outrageous Moment or Deepest Secret or whatever the provocative prompt is.)
posted by Metroid Baby at 10:39 AM on October 20, 2008 [1 favorite]

Don't write messages that are too difficult to answer. Keep them short and chatty with a focus on the other person, not just yourself, and with openings for them to respond.

It's highly likely they'll have a lot of other e-mails to respond to, and if yours requires too much of an effort then they'll put off doing so and then it will get forgotten.
posted by kerplunk at 10:41 AM on October 20, 2008

Seconding cider. Not too long, talk about what she wrote, and bring in a piece or two from her profile. Chatty is the key.
posted by rhizome at 10:51 AM on October 20, 2008 [1 favorite]

Response by poster: Thanks for your responses thus far.

One question - what would be the solution to a too-formal writing style? Should I throw in some random misspellings or what? Should I purposefully use bad grammar?

Seriously, this is a problem for me.
posted by Sloop John B at 10:53 AM on October 20, 2008

Don't write too much. You want a dialog not a monologue. I'm wondering if you're spending too much time thinking about the writing and not enough just chatting with her. I've been guilty of that more than I'd like to admit.
posted by valadil at 10:59 AM on October 20, 2008

Should I throw in some random misspellings or what? Should I purposefully use bad grammar?

Of course not. Just try to write the way you speak. If that seems too formal to someone you probably wouldn't get along with that person anyhow.
posted by ludwig_van at 11:00 AM on October 20, 2008

Yes, I agree with asking some questions to keep the conversation going.

Also - are you coming on too strong? Things that may be interpreted as coming on too strong include: giving out your phone number, suggesting meeting up right off the bat etc. There may not be anything wrong with these things for a lot of people but I definitely think that you need to let the woman be the instigator of these things and go at her pace (within reason), otherwise she may interpret this as being a bit aggressive.

Just my two cents - good luck!

On preview: I find absolutely nothing wrong with your writing style based on what you've written here and I would caution against dumbing it down. Typos don't bother me, but I would be put off by a real lack of attention to spelling or grammar. I can't imagine that anyone would hold good spelling against you, but the opposite might hold true for some people.

I think thus far you may have just had bad luck, unfortunately. Keep at it though - hopefully you'll find someone that was worth the wait.
posted by triggerfinger at 11:02 AM on October 20, 2008 [1 favorite]

One question - what would be the solution to a too-formal writing style? Should I throw in some random misspellings or what? Should I purposefully use bad grammar?

Oh, GOD, no -- bad grammar is one of the things that puts me off.

The best advice I got when it came to "informalizing" style came from a friend who was critiquing an essay I wrote -- she said "imagine that you're on the phone with a friend and you're telling them this story. Now write down exactly what you said on that phone call." There's a sort of light-hearted breeziness that comes across if you're more relaxed.
posted by EmpressCallipygos at 11:08 AM on October 20, 2008

Guys - what works? What doesn't work? (and by "work," I mean "get a positive response that continues the conversation.")

IMO It's email itself that doesn't work. Even if both parties are keen on each other, initially corresponding by letter is poison. Email is also time consuming, and if she has twenty guys sending her email, where is she going to get the time to write replies?

I suggest cutting the email right down to the basics - contact/chat info, so the intention is that further correspondence is via a medium that sucks less than email, and enough of a comment or response that it's clear you're writing to her specifically, not firing off template emails to anything with a pulse.

You can find out if you like someone far quicker and easier and more reliably even in mindless chat, than by email, so the sooner email is behind you, the better off you both are.
posted by -harlequin- at 11:09 AM on October 20, 2008 [1 favorite]

It's very hard to figure out what you're doing wrong (if anything) without seeing some examples. I think you're focusing too much on the technical part of writing (spelling, grammar, etc.) when your problem might be the content. If the person disliked the technical aspects of your writing enough to stop considering you, she probably would have stopped at your profile rather than contacting you.

Could you possibly paraphrase an email you've sent or give us some examples of topics you generally bring up?
posted by burnmp3s at 11:09 AM on October 20, 2008

I suggest cutting the email right down to the basics - contact/chat info, so the intention is that further correspondence is via a medium that sucks less than email, and enough of a comment or response that it's clear you're writing to her specifically, not firing off template emails to anything with a pulse.

Interestingly, harlequin, this has the OPPOSITE effect on me -- it sounds like a guy is just shooting emails out to everywhere and then offering his home email to whomever answers so he can pick and choose from the luxury of his email box at home. I usually like to trade a few on-the-personals-site emails before I give out more direct contact info so I know if I want to bother.

It's very hard to figure out what you're doing wrong (if anything) without seeing some examples. [...]Could you possibly paraphrase an email you've sent or give us some examples of topics you generally bring up?

Nthing this request. (I critique written stuff as a vocation, to boot.)
posted by EmpressCallipygos at 11:14 AM on October 20, 2008

Don't throw in random misspellings or bad grammar. Do use contractions and a casual tone. Try to use your speaking voice rather than a more formal writing voice.

This all depends what you're like when you're speaking, of course, but as an example: you may want to consider beginning with "Thanks for writing!" or "Great to hear from you!" instead of something like "It was such a pleasure to receive your email."

(I'm not trying to be snarky, but one example of what might feel "overly formal" in an email is saying "thus far" instead of "so far". Of course, if that's the way you speak, too, then you probably don't want to change that -- and the right woman won't care.)
posted by cider at 11:14 AM on October 20, 2008

One question - what would be the solution to a too-formal writing style? Should I throw in some random misspellings or what? Should I purposefully use bad grammar?

Nono. No. God, no. Speaking as a man who is dating someone he met on an online dating site, let me just say, the process can be cumbersome, but every person who doesn't write back because they're put off by how you write (be it content or mechanics) is someone you did not want to talk to in the first place. Trust me on this: there are awesome people who are on these sites, but they are wheat hidden in a sea of chaff. While it can be daunting to experience such a high apparent-failure rate, treat it as a blessing in disguise: it would be a whole lot more awkward if you made it to a meeting in person before discovering that you're on totally different verbal wavelengths. Then, bask in the gentle warmth of the ones who appreciate your long and unwieldy emails. Eventually you'll find one who writes her profile entirely in limerick (hi Jen!) or who nerds out over exactly the same things you do, and it will be grand.

You can't always identify the good ones through email, but you can sure spot the bad ones. Keep it chatty, ask questions that lend themselves to easy banter, and don't wait too long to move it to real-life meetings.
posted by Mayor West at 11:23 AM on October 20, 2008 [2 favorites]


If he's giving you his home email address, then he's not moving things to something more useful and easier than email, he's just trying to move to a more direct form of email (WTF?) so you're right to wonder, but if you're lumping in chat requests with that, your dragnet may be too wide. (An exception would be something like MSN where it's a really a chat request, but the username happens to be an email address because that's how the system works.)

Pretty much all dating sites have chat features built in these days, which can nicely sidestep the issue.
posted by -harlequin- at 11:27 AM on October 20, 2008

If she is writing you first (which is not that common), she is most likely writing e-mails to other men. Maybe one of them caught her attention before you were able to respond.

Girls - what do you look for in an online dating email? What makes you think "this guy is someone I would like to meet?" What are some specific turn-offs? How many questions should I ask in an email? How long should an email be? How can I avoid looking desperate?

I hate to reinforce stereotypes, but I want to hear that he is interested in me. You would think this would be obvious by the simple fact that you're replying to HER email, but a few questions about her profile will cement your interest. Desperate guys talk about themselves and talk themselves up. Creepy desperate guys talk about their fetishes and talk themselves down. Don't do either - instead, focus on her while slipping in some info about yourself. It's not an interrogation, though.

She writes (or her profile states): I currently live in Baltimore and I like to read.
You respond: Really, I used to live in Baltimore. Do you know [independent bookstore] on [whatever street]? They had great coffee. What kind of books do you like?

OK, that's a little stilted, but you get the point. Be yourself. I think your writing style is fine, if it's similar to what you've written here. I also learned to look past the occasional grammatical mistake, both because it'd be hypocritical if I didn't, and because I've learned that you miss out on a lot of great guys that way.

If you're comfortable offering your phone number, do so. My (now-husband) emailed me first, I responded, and he emailed back "Why don't we talk on the phone?" with his number. It's a MUCH better form of communication, it put me at ease because I knew he was for real, it felt much better than him asking me for my #, and we just got married 3 weeks ago.
posted by desjardins at 11:27 AM on October 20, 2008 [1 favorite]

Best answer: Write your email.

Cut out the unnecessary half.

Speak the remainder out loud.

Fix whatever doesn't flow out of your yapper nicely.

Replace at least one, but not more than two, periods with exclamation points.

Hit send.
posted by paanta at 11:34 AM on October 20, 2008 [8 favorites]

Response by poster: Hey all - sorry to keep poking back into my own thread.

A bunch of you have asked me to share some email samples, but I'm sure you can understand that this isn't very practical.

I'm really looking for general tips and "gotchas."

The advice about "informalizing" is helpful. I think this is an area where I especially need help; my writing style is way too formal. Any advice you can give me on this will be appreciated.

Some more specific questions -

+ Asking her questions is a good idea, but how many is too many?
+ Likewise, a reference to something in her profile is a good idea, but how many references is too many? Also, is it bad to have both profile references and questions in one email?
+ Length. How long is too long? It doesn't seem like there's much consensus on this.
+ To the women out there - when reading an online dating email, what are some "red flags" that make you think that the guy is desperate? What would be some opposite signs, indicators of confidence instead of desperation?
+ After how many exchanges is it customary to suggest a meeting? For example, is it safe to suggest a meeting after I've received 3 emails from her? Should I wait for four?

And as much as I'd like to think that this was just "bad luck," the sad fact is that I've been doing this for almost four years. I really think that I should be better at it by now.
posted by Sloop John B at 11:36 AM on October 20, 2008

You say you don't want to post your emails but would it be possible to maybe provide a sample email that women send you and we could craft a good response? Then you could kind of compare it to what you're writing.
posted by triggerfinger at 11:49 AM on October 20, 2008

Not to repeat myself too much, but for all of your questions, I think the answer is: follow her lead. If she wrote three pages and asked you forty questions, you can do the same. However, if she wrote a short note, you should respond with a short note (or a slightly longer note, perhaps). Ask one or maybe two questions. These can relate to things in her profile -- in other words, combine the questions and profile mentions into one thing. (desjardins's example was a good one).

Every woman will have different red flags, and what's a red flag to me might be endearing to someone else. However, don't say that you're looking to settle down, or that you're eager to have kids, or anything that you wouldn't say to someone when you were first meeting them.

I personally like meeting right away, but I understand that some women are turned off by that. After three emails, though, you should be safe -- if she doesn't want to meet then, she may never want to meet.
posted by cider at 11:49 AM on October 20, 2008 [1 favorite]

Response by poster: Oh, and one more specific question - how much does timing matter?

In other words, how long can I wait to respond before it starts to look like I don't care? Likewise, if I respond too quickly, is that a sign of desperation?
posted by Sloop John B at 11:53 AM on October 20, 2008

Best answer: Some of my male friends routinely paste me their dating site messages to girls. These are the biggest (and let me tell you- glaring) mistakes along with the impression created:

- Way too freaking long. More than like 3 sentences (unless girl in question herself wrote over a thousand words) is way too long. Don't you have things to do with your time? How much have you invested in this email, etc.
- Play by play commenting on things in the profile. Oh, my god, did you have two windows up when you did this? Don't you think being interested in every single thing I mentioned seems a bit disingenous? The best way to avoid this is to make one (1) joke based on something in her profile -- that's it.
- Telling her she's cute or seems interesting. Well, duh! "I think we'd get on fine" is also unnecessary, but doesn't always come out tacky, if you must.
- Sounding like a job application. Your profile is the job application. The email is more of a "hey girl, what's up?" (see: informalizing).

General tips:
- In general I'd worry a lot about doing the whole play by play setting up of pros and cons thing: this is what your replies are looking like.
- Most ladies over 22 do not like poor grammar. Many do not care about capitals, but don't throw in errors to appear "casual".
- There are no set rules for this. Your first email can suggest a meeting. Don't be shocked if she doesn't accept until you've chatted once or twice. People who want to talk forever probably aren't that interested in actually meeting up.
- Persevere. Sometimes you will hit on someone cleverly and they will stop replying. Trying again in a week or two could work ;) People are busy, etc.
posted by shownomercy at 11:54 AM on October 20, 2008 [2 favorites]

You are way overthinking this. I know it seems that from your experience, you are not giving this enough thought, but really, you are way overthinking this, and this amount of over-introspection will come off as phony and desperate. If a guy has obviously put as much effort into writing an e-mail as he would a term paper, that's a red flag. It shouldn't be that much effort to ask her questions and talk about yourself a bit. Again, don't interrogate, and don't go on and on. Follow the middle path here. Take cues from her; did she ask YOU a lot of questions?

Three emails is a good point at which to ask her out (see, I'm a grammatical moron). I personally never liked to drag it out past a couple of weeks, because at that point the time investment usually outweighed the possibility of us being a good match in person. You'll get people who DO want to drag it out. They're probably not interested in ever actually meeting you in person and are wasting your time.
posted by desjardins at 11:55 AM on October 20, 2008

In other words, how long can I wait to respond before it starts to look like I don't care? Likewise, if I respond too quickly, is that a sign of desperation?

If your profession involves sitting at a computer (which, given this thread, it apparently does), then I think a speedy response (less than 2 hours) is fine. I wouldn't go under one hour unless it's obvious you're online (i.e. the dating site shows when you're logged in). Unless you're stranded in the jungle, don't wait more than 24 hours to respond. Like I said, she probably emailed other guys, and she could have moved on to the next one. Strike while the iron is hot, etc.

Also, another clarification re: meeting. We've already made up our minds by the third e-mail. Anyone who still isn't sure she wants to go on a casual date (read: no sex) isn't someone who is social enough to meet anyone, and isn't someone you want to meet anyway.
posted by desjardins at 12:00 PM on October 20, 2008 [1 favorite]

Online dating can be such a crapshoot. The signal-to-noise ratio isn't too favorable, if my experience is any indication (and I'm female).

That said, you might try focusing less on rules or techniques, and more on showing genuine interest in the specific woman you're corresponding with at the time.

For me, it's gotta be personal. If I get the sense that a man who writes me is more interested in "meeting someone" or "getting a date" in the generic sense than he is in getting to know me, I become hesitant about continuing the correspondence. It's hard to put my finger on exactly what it is that gives me this sense, but the idea that there is some trick or technique (e.g., "always wait until I've received 3 emails before suggesting a meeting") that will magically enable the correspondence to continue is a red flag for me.

Some men come across as if they have a hidden, unexamined belief that women are some kind of alien species, rather than individuals with a full range of human traits. That's a big turn-off for me. So one of the things I look for is an indication that my correspondent has read my profile carefully and thoughtfully, and has some compelling reason for writing to me in particular.

There's no such thing as "too long" or "too many questions" in the abstract; no consensus is going to emerge here, because this varies greatly from woman to woman. There's only what matters for the particular woman with whom you want to correspond.
posted by velvet winter at 12:48 PM on October 20, 2008 [1 favorite]

If he's giving you his home email address, then he's not moving things to something more useful and easier than email, he's just trying to move to a more direct form of email (WTF?) so you're right to wonder...

This could indeed be a your-mileage-may-vary thing. I've sent out initial emails to men who've responded by saying "hey, thanks for writing, here's my real email, can you write me there instead?" and not saying anything more. I've also had guys do the same but offer their phone number. And once I had a guy respond by asking me out to a movie. Twice. In a half hour. The first two came across as "I've got so many irons in the fire that I need to have people come directly to me because I can only concentrate on what's directly in front of my face," which to me was off-putting. The third just was....really desperate sounding.

But I'm not mentioning it because I think there is one Gold Standard for internet dating activity (she said, turning back to include Sloop John B in things), I'm mentioning it to say exactly the opposite. SJB, you're asking for specifics in a field when there actually may BE no specifics. There is no one universal constant that every woman in the world is going to find appealing/unappealing, forward/laidback, offputting/endearing. I personally like more distance right at first, other women like to cut straight to the real phone number. Some women like it when you're chatty, others think it looks like you're trying too hard -- there is no one hard-and-fast rule for how many questions to ask, how many emails should pass before you suggest a meeting, etc., because every individual woman will have her own comfort zone for that.

The one thing we CAN help you with on a specific level is "how do I sound less formal", because that is more about your own personal style than it is "tailoring your style to guarantee a response". The latter is about trying to predict others' behaviour, which is impossible; the former is about you, which you CAN control. And that, I think, is why some kind of a sample would be helpful, because we can break it down and go "ah-ha, see, HERE is a passage that sounds like you're writing a Master's thesis and here's why." You're still going to have people that don't like what you write no matter WHAT you do, but at least you have identified something you want to do for your own self in general, and there we can help.
posted by EmpressCallipygos at 12:56 PM on October 20, 2008

Response by poster: Okay, I feel like this thread is starting to go off the rails a bit.

Yes, I'm asking a lot of specific questions here. But the fact is this - as a guy in my situation, the only feedback that I ever get is an unanswered email. This is unhelpful and tells me nothing. So I'm just trying to see this from all different angles, and figure out what I've been doing wrong. Obviously I'm doing something wrong. That's why I asked the question.

I don't think there is any "trick" or "technique." But obviously, judging from other responses in the thread, some things are just bad ideas.

Anyway, I'm starting to get some nasty vibes from this thread, maybe it's best to just ask one of the admins to close it up.
posted by Sloop John B at 1:01 PM on October 20, 2008

Specific answers to your questions:
  • Any more than three questions tops is probably coming on too strong. Keep it short and simple.
  • You should be able to manage both one or two profile references and your email responses in a single email.
  • I'd aim for two short paragraphs, three max. Show you care, but no need to overwhelm.
  • I'm not a woman, but I had decent luck when I was doing online dating. I think you try to match the tone and length of the email sent. If she's earnest and thoughtful, respond in kind. If she sends you a flip one-liner, go with funny. In fact, in general, the funny wins so if you can find space for it, use it.
  • I tended to suggest a meeting early, after two or three email roundtrips. But, you've got to do the request right. The two rules I followed was:
    1. It's a preference, not a an ultimatum. Provide the option for further email communication.
    2. Don't ask for specific events or day/times, just a general interest. That way if you get rejected you're not wondering if they're rejecting the specific option (e.g., "Sorry, busy Friday" or "I hate bowling!") or you in general.

I'll open myself to almost certain internet ridicule by offering up something in my own personal style (I'd use a real one but has deleted all my old entries since my profile has been inactive for so long) to give a general feel as the type of response that seemed to work well:

Hey <profile_name> ,

Thanks for responding! Yeah, I really dug <book you mentioned from my profile in your email>. I kept thinking, "Get out of my head, <book author>!" I'm looking for a good read for my long subway commute right now. Would you say <other book mentioned in profile> is accessible in subway increments of nine stops or less?

While I love the messaging back and forths as much as the next guy -- Hey, pipe down, next guy! -- it can get a little tedious, no? Any interest in catching a beverage in the near future and telling me more about <funny thing she said in her profile>? Of course, if you would like to do more online sussing out, suss away.

Talk to you soon,

<My real name> I always enjoyed the little thrill of learning someone's real name. (e.g., miss_fancy_pants == 'Veronica', neat!)
posted by funkiwan at 1:03 PM on October 20, 2008 [9 favorites]

Timing is a minor point, but I disagree with desjardins, I think two hours after the initial e-mail would be too soon. I hate to sound phony, but a big part of the reply seeming casual (and not seeming desperate) is acting as if you have other things going on in your life, and that getting an e-mail from an interested woman is no big deal, and doesn't warrant immediate attention.

Keep in mind that since she contacted you first, the potential for rejection will be going through her head as well. Giving a little time for potential anxiety/anticipation to build can possibly make your reply that much more interesting, even before it is read. I think giving it anywhere between a day, to two days is ideal, any longer than that is entering rude territory.

It may just be me, but being upset by someone taking a day or two to respond to an initial e-mail would indicate some very unattractive character traits anyways.

Oh, and make sure you are giving THEM enough time to respond, up to and including a week or two. After all, would you rather find yourself with the kind of person who was waiting at the computer hitting refresh on browser for new e-mails every hour, or someone who might only check a specific e-mail once a week because of all the incredibly interesting and time consuming things they have going on in their life?
posted by paradoxflow at 1:23 PM on October 20, 2008

I really like that message you wrote, funkiwan. I can see why it worked well.

It's a clear expression of interest, with specific reference to something mentioned in the person's profile. It asks a question and invites the recipient to respond, without sounding overbearing or presumptuous. You come across as lighthearted and fun, and you make your interest in a face-to-face meeting clear, while still allowing ample room for the recipient to continue the correspondence via email if that is their preference.

Nice job!
posted by velvet winter at 1:24 PM on October 20, 2008

I like to think of online dating email as a special form of flirting. And flirting follows many of the same rules as improv comedy: the goal is to be fun and engage curiosity and interest by playing with expectations (in a respectful way), and in general keeping the momentum moving forward. So answer questions, but you can leave parts of questions hanging in a way that invites more inquiry. It's like playing with a cat -- they're shy, so you don't want to scare them away, but you also want to draw them closer with their claws sheathed. If either party isn't enjoying the game, they'll give up.

Here's a great guide on how to be a better improviser. The "Yes, and ..." rule is crucial.

The other thing is to listen to what they say, extremely closely. Treat every statement as a clue to their interest and personality. See if you can follow up on unusual aspects of their profile. In flirting, the other person will almost always give you a subtle clue to their true desires. Sometimes it is left deliberately ambiguous, in order to leave an escape route. So your job is to tease them into more revelations, but not force them into the open before they are ready.

At the very least, if you are attentive, clever, and really interested in what they have to say, they will be interested enough to want more interaction.

You can suggest getting together after 2 or 3 exchanges, depending on how much she's started warming up to you. I recommend avoiding a dinner date-- it can be intensely awkward if you discover you don't really like each other. Coffee / tea or a stroll at a park gives you an easy out if necessary. Be sure to have an option for continuing the conversation if things are going well. Casual activities (as simple as bowling) are great.

I recommend reading books like Dale Carnegie's How to Win Friends and Influence People, and Malcolm Gladwell's Blink. Both quick reads, with a bit of insight into basic social interactions.
posted by Araucaria at 1:29 PM on October 20, 2008

One other question — are the only women you're contacting the ones who contact you first?

If that's the case, you're getting a very skewed sample.

Muster your courage and start sending out unsolicited emails. I would consider a 1/10 response rate a success. At the very least, you'll get a broader sample size, and if your writing is as good as you say, you might be more successful than I was.
posted by Araucaria at 1:48 PM on October 20, 2008

What dating service are you using? If it's Nerve / Spring Street Networks, your lack of response may have nothing to do with your emails.

I used to use that service and this used to happen to me. Then I would often see profiles from users that would say, "sent you an email in the last 3 days" or whatever the language is that they use. However, the emails were never in my inbox.

I then noticed that the email section of the service had multiple "inboxes", one of which was labeled "junk/bulk" and it had the same number of emails in it as people I noticed had sent me letters. I tried to open this box but was denied by a message that said I had to contact customer support. I did, and of course they never responded.

I never found out what the emails said, never heard back from customer support, and now refuse to give them anymore cash as they're friggin thieves in my book. Whatever service you use, see if there is some filtering going on.
posted by Manhasset at 2:16 PM on October 20, 2008

My advice (from a female):

Keep it short, i.e. one paragraph. One or two questions...simple chatty ones, like, "oh, you mentioned you work in the finance field in your profile, do you like it? or "How long have you lived in the area?" not "What are you looking for in a partner?" or "Tell me about your religious beliefs."

Turn ons: Friendly, non-agressive tone. Suggestion of meeting IRL for a cup of coffee or a drink. I don't want to get to know someone through email.

Turn offs: Bad grammar. Pushiness (things like "I think we'd be a great match!". I mean, you haven't even met yet. Same with "I'm looking for a partner and a best friend.") The use of the words "sexual", "sensual", or "comfortable with her body." (unless you're on a casual encounters type site)

In summary, keep it short,sweet, and simple. Good luck!
posted by emd3737 at 2:23 PM on October 20, 2008 [1 favorite]

I didn't read every response, so I apologize if I repeat something.

Not everyone can list letter-writing as a talent, so not all of us can really "sell" ourselves in an online ad. Doing PR for yourself is a tough gig.

But there are some things you can do:
Be specific. Don't say "I like to read." Say "I like to read books by Salman Rushdie and James Patterson." Discuss what you like about them. Don't say "I like having a good meal with friends." Say "I love KFC and a Bud Light" or "Pad thai is my favorite food."

Don't be overwhelming. "Keep it short" is good advice. Ask about her (show that you read her profile but also thought beyond it) so that she has a specific reason to write back. Thrown in a fun fact or two about yourself.

And I really don't think it's wrong to ask for help. Run your answer by a female friend. Or, if writing really isn't your strong suit, you can even get some help from a service like that helps you sell yourself in the online dating world.
posted by cherie72 at 2:35 PM on October 20, 2008

Shakespeare himself said that brevity is the soul of wit, so remember that. Answer her questions, maybe using an interesting anecdote if you have one to provide. And don't ask more then one question, just one that will leave it open and easy for her to respond. You want to seem interested in furthering the conversation but not too pressed for it. Also, I would wait a little bit, but I think a day or two is your max for response before it seems obvious.

Also is there a photo of you in your profile? Do they see that before they email you the first time? If not, are you ugly??

Anyways, good luck brother!
posted by BobbyDigital at 2:37 PM on October 20, 2008

I'm a bit late to the party, here, but I have some experience with online dating and thought I'd chip in.

Regarding messages, the two factors that determine whether I reply are not are 1) your spelling and grammar, and b) whether you have obviously read my profile. I get a lot of emails that are obviously sent to loads of women, and I never bother to reply. Don't pick apart every sentence in my profile, but I like messages that refer to several things in my profile. More than just one.

On the other hand, if messages are really long then I feel I have to send one of a similar length, and it seems a bit daunting so I never get round to it. (A guy sent me a great message a few months ago - it was funny, and tailored to my profile, and was really interesting. But it was really, really long and I spent ages crafting a reply and wasn't satisfied and put it off and then it was too long after his original email and I felt silly replying. I really regret that now - it's still been the best message I've ever got on the site.)

How soon you suggest a meeting should also depend on how near each other you live, and how complicated meeting would be. If meeting up requires a three-hour train ride, then suggesting meeting for coffee on email 2 is probably not going to get the best result. You could suggest phoning, though. Skype can be good if people feel weird about giving you their number.

Also - my exboyfriend suggested meeting up when we'd been emailing for two weeks. I balked a bit, but agreed, and he was a little pushy on the first date. To me, emailing doesn’t replace hanging out, getting to know how the other person feels and moves, shyly touching each other, the silly flirting. Just because I've emailed someone a few times doesn't mean I want them to lunge at me the minute the lights go down in the cinema ten minutes after meeting them...

With timing, I generally reply to messages a couple of days after I get them. This is mainly because I'm crap at replying to things in a timely message - I don't want to send instant replies because then I'll look pathetic, but then I forget and leave it much longer than I'd meant to. But I'd find it a bit odd if people sent replies within an hour. OK, once or twice would be fine but consistently would put me off.

However, I get the feeling that other people in this thread have completely different opinions. Just because we're talking on the net instead of meeting in a bar, it doesn't mean that we've suddenly all become one person. The normal rules of human idiosyncrasies apply! That's the point I really want to stress: everyone's different. Sadly there are no easy rules. The only thing I can suggest is to take your cues from the other person.

Good luck! From what you've said, you sound much better than most of the people I get emails from...
posted by badmoonrising at 3:01 PM on October 20, 2008 [1 favorite]

OP - you come off as "desperate" in this thread. Desperation is a natural human emotion and all people experience, but to be good at anything, you can't be desperate about it. Learn to hide it. You characterize yourself as having been at this for four years with no success and are asking for very specific and nonexistent rules for success.

I'm in sort of a similar situation. However, just a few days ago I had some great success (for me) on a dating website - messaging and getting responses from 3 girls and engaging in simultaneous chats with all of them.

Getting non-messaged hurts, but the trick I use is to ask myself "do I need this person to respond to me?" Sometimes the answer comes back yes, sometimes I realize its absurdity. But the point is I'm always aware of it.

When you need a person to like you, you are coming from a deeply selfish state of mind. Desperation manifests selfishness, and people can pick up on that and are turned off by it, because it is rude and dangerous. I find with myself a lot of times all I'm really seeking is the person's validation. If I get a response, I immediately lose interest in the person. I 'won'. That is very selfish, and who knows, maybe what happened to you.

So anyway, I think it would do you well to get in touch with your own level of neediness and desperation, and just be aware of how it guides what you say and what you do.
posted by norabarnacl3 at 3:44 PM on October 20, 2008

For what it's worth, I think the type of profile you have and the messages you send depend on what sort of person you're trying to find. My profile is a bit long and different, and my correspondence is the same way for the conscious reason that I'm pretty sure the type of girl I'd mix well with would tolerate (and perhaps appreciate) this.
posted by sinical at 9:23 PM on October 20, 2008

Response by poster: Hey all,

Thanks for your help. Although a few responses were mean and antagonistic (and missed my point completely!), most of you were really helpful.

I don't think there's anything wrong with wanting to improve my communication skills. Just because we're talking about online dating emails instead of, say, memos or term-papers, doesn't mean that I can't find better ways to express myself. I think it's a shame to miss out on making a connection with somebody because of awkward phrasing or what-have-you.
posted by Sloop John B at 7:03 AM on October 21, 2008

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