I need a first chance to make a first impression

May 1, 2007 6:47 AM

What should I put in my first email to someone I found on an online dating site?

I've read through lots of the Ask MeFi threads on this subject (13 tagged onlinedating, 4 marked dating and online and a slew of others), but still haven't really found the guidance I'm looking for, so here we are.

I have an account on an online dating service. I log in, view lots of profiles, read about many women who seem very interesting to me, and then.... I do nothing.

I find the first email to be just as awkward as going up to a stranger in a bar, which I never do, except I know a lot more about her than if we were in a bar, and she will know more about me. In fact, it's even more awkward, because there's a lot more information in play, which means the rejection might actually be based on something. (Although, I don't always know useful information, since lots of women all share an interest in going out or staying in, dressing up or dressing down, and family and friends! But that's a separate discussion).

This is not a minor hurdle for me, for some reason. I've been a member of the site for a few years, and have only emailed or IM'd complete strangers a handful of times.

I'm not normally shy or particularly introverted. I do well in groups, and fine with individuals once I've met them. It's the meeting and making a first impression that I'm stuck on.

For those of you who have tried online dating (match, yahoo, nerve, okcupid, jdate, whateveryourkinkis.com, etc.), what makes a good first email? I'm a guy looking to meet a lovely lady, but I'm happy to hear from anyone with thoughts on the issue.

How long should it be? Should I mention if I think she's cute? Generally, I've had good luck with sincere compliments in person, but another thread said that was a generic thing to put in an email. Will that sound like every email she gets? Should I comment on specific things in her profile? What do I say about me? She can click on my profile for the basics, so I don't want to repeat it all, but it seems presumptuous to assume she's going to read the profile, right? Should I specifically ask her to read my profile? Do I say i hope she'll write back, or that I'd like to meet her, or that I'd like to chat?

And so on... I get all wound up on what to say and end up never saying anything. Help!

posted by anonymous to Human Relations (32 answers total)

Keep it short and sweet and avoid generic compliments ("you're cute" etc). Your goal is to intrigue her and have her write back. Mention something interesting about yourself without going into details, make a point of noticing some little thing in her profile you think most people probably skip right over, compliment her writing style (if, of course, you actually like it). If she's interested, don't worry, she'll read your profile without your telling her. And good luck.
posted by languagehat at 7:00 AM on May 1, 2007

Just say,

Dear [name],

I found your profile on [site] and you seem like a really interesting person. We both enjoy [listed profile interest]! If possible, I'd really like to get to know you better.

Of course, you can look at my profile to learn more about me, and if you have any questions, just ask.

I hope to hear back from you soon.

Sincerely, [your name]


Don't comment on her physical appearance or her pics. It just comes across as creepy and lecherous. If she is attractive, she knows it. If not, she knows you're just flattering her. Just don't comment on her appearance at all until you actually have a conversation with her, otherwise it seems like your hearts not really in the right place.

If you don't have any interests in common, I don't know if sending the email is such a good idea. Because then it seems like you're just in a broad sweep, sending out dozens of emails hoping someone will respond. So I think it's good to be specific and connect with some particular aspect of her profile, such as an interest you have in common, books/movies/music you both enjoy, etc.
posted by crackingdes at 7:08 AM on May 1, 2007

You're having trouble because it's hard. The more generic the profile, the harder it is.

I think the best strategy is to hang a short email on a hook from her profile. Be sincere, there's no real need to pay a compliment, as the assumption is that you're emailing because you find something about her attractive. Close with a question that is raised by her profile but not answered, and invite her to write back if interested.

Don't take rejection personally, there really isn't enough in a profile to warrant a personal rejection. There's enough to warrant a rejection based on quirks (she hates asparagus and you mentioned it as your favorite veggie, or she loves Barney and you slightly disparaged him while talking about your cute nieces), but that can't be controlled and has nothing to do with you.
posted by OmieWise at 7:10 AM on May 1, 2007

Um, okay. Real answer. The dating website you're using matters. I mean, if it's Ok Cupid, the tests are a great place to start. "Oh you got --- on such a test, I got ---. I guess that means maybe we'd make a good match?" Something like that. A bit corny, but it can work.
posted by Deathalicious at 7:23 AM on May 1, 2007

I tried out online dating a couple years ago and here's my advice:

Your first contact should be brief. It basically should let her know your interested without being the cop-out "wink" that some services offer. Some evidence that you read her profile is recommended. A typical opener:

Hi [girl's name],

I just read your profile and thought I'd say "hi" and [compliment something from her profile, such as her taste in music, her dog, etc].

[One or two questions referencing something in her profile, e.g., "Where would you love to travel that you've never been?"]

["Write back," or "Look forward to hearing from you," etc.],
justkevin

Keep in light. Experiment with different openers.

Whatever you write, don't be disappointed if your dream girl doesn't write back. You could be Brad Pitt with Cyrano de Bergerac feeding you lines and not hear from half the girls you write to.
posted by justkevin at 7:45 AM on May 1, 2007

The first email is just as difficult for her as it is for you. Your best chance of getting an answer is by making it easy for her - ask an interesting question based on her profile, so she has an easy topic of conversation to respond with. Make it about something you have in common. Examples:

So you like [some band listed in her profile]? I saw them play a great show at [wherever] last summer - have you ever seen them live?

Hey, I love [that author she mentioned] too. Have you read anything by [another author you like that is similar]? I really loved [a book by that person], and you sound like the kind of person who might enjoy it.

I've also been won over by extreme honesty:

Hi. I'm not really sure what to say here, but I found your profile intriguing and I'd love to get to know you better. How's your week going?

posted by vytae at 7:46 AM on May 1, 2007 [2 favorites]

I married Mrs. Procrastination through an online dating site (in a roundabout way). I can't tell you what to write, because that depends deeply on you; you want yourself to show through. I think writing something personal about what you have in common with the person that you are writing to and something that shows you read their profile and have a reason to be interested in them is the way to go. Tell a story about it, or a joke, or something unique. This helps more than a generic "check me out and write me if you want". Women get many more responses than men do, and most are like that. It is hard to stand out.

How do I know? During my online dating time, I conducted an experiment. I posted a fake female profile which I left up for just a couple of days. I know, I am a bad person. But reading what other guys wrote was quite an eye opener. I immediately saw that what I was doing when I contacted people was just noise in the crowd. The majority of answers were very generic, some clearly just cut-and-paste jobs that were sent to everyone.

I would actually recommend doing this for opposition research. See what other guys are writing on a first contact so you can stand out. You could also just ask a female friend to share her messages with you, if you know a woman who is doing the online dating thing. Also, do searches for men who are similar to you and make sure your profile isn't just some other generic guy profile. It is hard to put yourself really out there, no doubt about it, but I think it works better.
posted by procrastination at 7:47 AM on May 1, 2007

I'll repeat what others have said: make sure that you refer to something in her profile that interested you. Many of my friends get amazing amounts of messages at those sites, and from what they say it's obvious that some guys are just spamming everything in a dress to try to make contact.

Make sure your profile is interesting. One of the main purposes of your message is that it acts as a pointer back to your own profile, which is where you should spend time being witty and creative and all that.

Tying this all together: you may not get responses to all (or even many) of your messages. It doesn't really say anything about you - seriously, women get dozens of messages and I know some of them don't have time to read them all. So keep it short, refer to something in her profile, and don't get discouraged by a few rejections or non-responses.
posted by flipper at 7:47 AM on May 1, 2007

Oh, and like others said, do NOT compliment her appearance. It comes off as creepy, no matter how much you mean it.
posted by vytae at 7:47 AM on May 1, 2007

"Sincerely"?

Skip the formalities, just ask them a few questions, as if you were already in mid conversation. That's assuming they have some books or movies or hobbies listed:

"So did you get to see either of the film versions of Lolita, or are you just into the book? I just saw the Kubrick version for the first time and was pretty surprised."

No agonizing over greetings, closings, content about yourself. Giving them a few leading questions to answer is all the kindling you need for starting a conversation. Trust me, they'll answer if they're interested.
posted by hermitosis at 7:48 AM on May 1, 2007

Lurking on a dating website is kind of pointless. Also remember that you may find the love of your life after looking at a person's profile while they may not feel the same about you. On dating sites you need to almost use the shotgun approach. Find many women who meet your criteria and email them ASAP. Don't do form letters or you will get nowhere.

Be aware that unless you are a hunk and have a profile that portrays you as such, you probably won't get many responses. For the most part it is a learning process. What works for one person may not work with another.
posted by JJ86 at 8:17 AM on May 1, 2007

I've used a number of dating sites over the years and know many people who have as well. Several married friends of mine met their spouses that way.

The one thing I have heard over and over again from the women I know who used the sites - both the ones I met and dated and friends - is that the thing that made the biggest impression on them was a mail from someone that clearly indicated that they'd actually read their profile.

Women get a lot more responses than men on most sites and weeding out the ones who were just blasting the same form letter to a lot of women cut down the volume by 90%, according to my friends.

Beyond that I'm not sure there's many universal qualities you have to have in a letter. My friends would likely think less of you - but not all of them would just reject you outright - if your letter was poorly spelled and punctuated. If you don't care enough to be articulate initially you're either inarticulate all the time or not putting in the effort. A bad sign for some people, but it may be that this would matter less to a different age group (we're all in our 30s in my circle).

As far as it being awkward - well, duh. Dating is awkward. Accept it and deal. Awkwardness almost always fades quickly and a lot quicker in the face of meeting someone you like.

I wouldn't be shy about repeating something from your profile if it's pertinent. Assuming she'll click through to your profile - possibly a leap in itself - doesn't mean that she'll necessarily notice the characteristic you think might be important to her. I wouldn't bother to ask her to read your profile - if she's on the site, assume she knows how it all works.

And there's nothing wrong with indicating you would like to hear from her, even though it's obvious. People like to be liked, so long as you're not a needy/desperate stalker.
posted by phearlez at 8:22 AM on May 1, 2007

I’ve tried OKCupid, Nerve, and Consumating (I’m a woman). It’s true that women get a lot more email than men do, so you do want to say something that distinguishes you—or in a way that distinguishes you. I’d stay away from the generic form letters posted above—I mean, at least they’re not creepy, but they’re not super interesting, either. Do not: compliment her appearance (maybe some girls like it, but I hate it—do that in person!) except maybe her smile, if it’s a good one; suggest meeting up right away (when a guy does that, I question his motives—how ’bout we get to know each other a bit more first?); or talk overly much about “what [you’re] looking for”—you should be sending a message because you think she sounds interesting, not because you’re hoping she’ll tell you just how she conforms to your criteria. Also, don’t suggest that she “check out [your] profile!” I do that almost immediately, and I’ll bet other girls do, too.

Instead: identify a common interest (hermitosis’s suggestion is a good way of doing that); make the message relatively snappy; and feel free to say that you’d like to hear from her. (If she responds, you can suggest continuing the conversation by personal email or IM screenname; my personal preference is that phone numbers or invitations to meet come out in the third conversation at the earliest.)

Two stand-out first messages from my experience (paraphrased, of course): One guy wrote saying that he’d been trying to copy down my username, so he’d hurriedly pasted it into a graphics program he was working in, and it looked cool in block letters, like the name of an architectural firm. Then he said he found my profile interesting, especially my value system; mentioned that the “written word rules [his] life, too”; and asked what kinds of books I work on. This note caught my attention because I could tell from the first lines that he was creative; I could ask him questions: why he was working in such a program/what he did with it; and I could tell that he’d read my profile.
The second: I’d left a note on his profile asking “what’s your favorite poem by [poet mentioned in his profile]?” He wrote back with a poem, and asked if I had a favorite. The interaction was short and sweet, but already we were talking about something a little more personal than the usual “what’s your favorite food?”

Don’t sweat it too much. If she’s not interested, she won’t write back, but it’s not really a rejection the way it would be in a bar. Just move on to the next one.
posted by CiaoMela at 8:33 AM on May 1, 2007 [1 favorite]

I agree with keeping it brief and with making it clear that you have actually read her profile. Also, just for your personal dignity, if there is no response to your first email, don't send a series of follow-ups ("hey, my last email must have gone missing, so instead I'll write to you every hour..."). No response = move on. You also need to not get discouraged by non-responses and brief "no thanks" responses (or even by the people who get into long email exchanges with you... and then drop off the face of the planet with no explanation). It is sort of a buyer's market for women on dating sites -- they often get lots of emails (albeit of very low quality), and are often wary of sending a "no thanks" email in case the guy turns into Mr Stalker and won't take no for an answer.

I really like the idea of doing opposition research, by having a fake profile or having a friend share her experiences. Also, do you have anyone (sister, cousin, friend) who shares your tastes and can say whether or not your profile a) would attract her and b) represents you in the best way possible? (There are also commercial services that will do this for you -- there was a big article a month or two back in the LATimes about it -- but I don't know if it is worth the money or not. One way or another, though, you do need to get a second set of eyes on your profile to make sure it is working for you.) Also, is your photo flattering? People put the worst photos up on dating sites; a good photo will help you stand out.
posted by Forktine at 8:33 AM on May 1, 2007

yeah, I think a lot depends on what kind of site you're on to start with. If I got a generic formal email like what crackingdes wrote above I can't imagine I'd bother to look at the profile, unless maybe the pic really caught my attention. What vytae & hermitosis have said fit with my experience - quick little notes with some specific reference that can start a casual exchange. Sometimes the exchanges will then move to email, and eventually to a date, and sometimes they won't. At the beginning, IME, you're just looking for light banter & shared interests.

But, it may have more to do with the culture of the site you choose - if the profiles you're responding to only include information about dressing up and dressing down, then perhaps all they want is to know the generic stuff. There isn't really a right or wrong way to do this: it's a question of who is going to respond. Someone with lots of interests is going to want to know what you're into, while someone who just wants a decent guy within a convenient distance doesn't need much more than "hey, what's up" (but that working out will be largely a matter of lucky timing).

I'd say, remember this email is her first impression, so just try to give her something that is moderately accurate. If you love to read find a way to reference a book, or if you adore the outdoors maybe work in something about a recent trip, etc. Give her some little sliver of specific information, try to ask her something so that she can respond easily, but at the same time keep it easy-going and non-formal.
posted by mdn at 8:35 AM on May 1, 2007

Given that this seems like you have someone in mind, here is my 2 pence on what to write. Much of this is based on advice I got from an Online Dating set of DVDs that I watched - I was sceptical, but the results don't lie.

Essentially, think about things from her perspective. Women get *far* more messages from guys than the other way round, so you need to stand out. The best way to do this is in the subject line to make some sort of passing reference to something in her profile, that show that you "get" her. For example, I emailed someone with "caligirl" in her name, so I guessed she was from California, and my subject line was "I wish they all could be..." - she loved it.

As for the message itself - keep it short. It will creep her out if she thinks you are sending obsessively scripted emails to her specifically. At the other extreme, it should not be so generic that you could be mass mailing. Again, make reference to something in her profile briefly - if possible, tease her about it!

It will seem counter-intuitive, but it is also a bonus to be a little bit arrogant. Something like - "your profile was interesting, but I still don't feel I know you - tell me why I should spend my time chatting to you - what makes you special". This positions you as a guy who has plenty of girls to talk to, and only wants to deal with the special ones.

I should add, none of this is intended to be manipulative - it is all meant genuinely, and is about making sure that the two of you have a chance to make a connection without just getting filtered out as "one of the crowd".

Oh, and she will read your profile before she replies, so get a professional photo done, and re-read it from her perspective. You want to put the "best you" forward. Don't lie, but just like on a resume, put things in their best light.

Good luck!
posted by csg77 at 9:03 AM on May 1, 2007

Presumably something she wrote in her profile was interesting to you. Ask her about it! Don't force anything, and don't try too hard. She might not message you back, but don't let that discourage you -- women get to be choosy in the online dating pool, and that's fine. It's no indictment of you, just how the market seems to operate. Keep trying. :)
posted by Alterscape at 9:11 AM on May 1, 2007

As said above, keep it pretty short and sweet. Your profile should do most of the talking for you. But you should hit a few key notes:

1) Show that you read her profile and actually found something interesting about it and you're not just spamming her or sending out a feeler based on her picture (girls get a LOT of that)

2) Ask a few questions. Give the email exchange somewhere to go, conversationally. You don't want her to be just as square-one-awkward about writing you back. So ask a question or two she can answer. It also shows you're interested and want to listen and know more about her, which are both good things.

3) Make a provisional offer to meet. I'm the kind of person who feels you can get to know each other over email a little bit, but some think of the computer/internet as a means to an end, a poor substitute for "real" connections. Not everyone wants to talk a lot over email. If they're interested, they want to stop with the online stuff as quick as possible and proceed with a real meeting. But mention it casually. You could easily be too forward with this. I'd put it out there but in a very generous "if you're interested" kind of way. Say something like "I hope to hear back from you. Let me know if you'd rather talk by phone or get together for coffee." You could also save that for your second email - use your judgment.

Good luck!
posted by scarabic at 9:18 AM on May 1, 2007

It will seem counter-intuitive, but it is also a bonus to be a little bit arrogant. Something like - "your profile was interesting, but I still don't feel I know you - tell me why I should spend my time chatting to you - what makes you special".

Um, no, it isn't a bonus to be arrogant. I would immediately delete any message I got along these lines.
posted by amro at 9:19 AM on May 1, 2007

I've used dating sites several times over the years and as a female, I can tell you the following based on my experience:

It does not matter what you write (within reason) if some ineffable quality that speaks to our possible chemistry does not come through. You could write the greatest first email of all time but it won't make an ounce of difference if you're just not the right guy for her.

I guess what it comes down to is write brief emails to the girls whose profiles interest you, and do make sure to indicate that you've actually read it. Best way to do that is to ask her to elaborate on something she's said in her ad. Leave out the compliments. The point isn't to woo at this juncture, but to start a conversation to see if wooing should commence.
posted by hollisimo at 9:23 AM on May 1, 2007

And amro is totally right. The arrogant crap would head straight for the round file.
posted by hollisimo at 9:29 AM on May 1, 2007

Met wife through Match. Great ideas above...

2nd email question:

If you could have the perfect day, and time & money were no object, what would you do? Why? Thorough explanation will show what they like and whether they want to look good (save dolphins) or be honest (brady bunch marathon).

(E.G. Breakfast in Milan, Arctic Circle for some Northern lights, lunch on Rodeo drive, Afternoon to the riviera to look at man meat & dusk at Ayer's rock.)
posted by UncleHornHead at 9:30 AM on May 1, 2007 [1 favorite]

It will seem counter-intuitive, but it is also a bonus to be a little bit arrogant

Um, no, it isn't a bonus to be arrogant. I would immediately delete any message I got along these lines.

This is again why there is not a right or wrong way to do these things. "Caligirl" may love self-important studmuffins. It all depends who you want to impress. If you want to instigate some kind of jock/chick match-up, then read those Rule books/ DVD guides and follow the traditional roles until you too have achieved the appearance of a relationship. If you want to get to know another human being, introduce yourself honestly but without expectation, and see what (if anything) happens next.
posted by mdn at 9:46 AM on May 1, 2007

Second hollisimo.

IME, saying something that would make her smile (or laugh in a happy way) also helps.
posted by whitneykitty at 9:51 AM on May 1, 2007

vytate has the right idea.

You should write your email as though you're continuing a conversation that she started with her profile. Find something you have in common or that you find interesting (You're really a lion tamer?) and use that to give her something to focus her response on (Is there a school for that?).

If she's swamped with responses, she'll appreciate that you've taken the initiative to find a topic of conversation. So many people just say "check out my profile and write back if you want" which may seem reasonable at first, but then the ball is in her court to find something in common and start the conversation. Given that she's probably got other emails to deal with, the ones that require the most work on her part are probably going to fall by the wayside.
posted by stefanie at 10:21 AM on May 1, 2007

Last August, I checked my OKCupid account after a few months of neglecting it, and found a several-week old email from one of the other users. The subject line was "Wow, hello," and the first line included the words "we must meet."

The email was pretty brief, just two paragraphs, and it referenced our common goals and interests to back up his "we must meet" claim. The closing? "What else do you want to know about me before we get together over tea?"

I speak only for myself, not for every woman out there, but I found the email format really compelling. Unlike all the "hey babe...wanna cHat?" spam that finds its way to my inbox, and even more unlike the formulaic epics in which men desperately try to share everything they can think of about themselves in one 10,000 word email--correctly guessing that they are not going to get another chance to get it all out--the email showed genuine interest of the "wow, you seem awesome" variety and exuded confidence.

I use that as an example in part because it has the elements in place that I find important: brevity, genuine interest, rephrased examples of shared interests, confidence, and help seeing the next step. It's basically good cover letter protocol.

The other reason I use that example is because it worked. We met a week later, and have now been together for almost ten months.
posted by bloggerwench at 1:51 PM on May 1, 2007 [2 favorites]

Spell correctly. dOn't WRitE LikE THis. Don't use aim lingo (lolz, omg, stfu).


My first email to my SO on OkCupid.com was something like, "Hi." But, I'm female, so I guess I had some advantage. Good luck.
posted by nursegracer at 3:35 PM on May 1, 2007

Disclosure: my experience is from Nerve. YMMV, and all.

Your intro letter is only half of the equation: you've got to have a fun, compelling profile for your potential sweetie to click back to. Nothing about the online dating scene is meant to be taken too seriously, until you get that meetup with the one who gives you tummy flips and makes you all googly inside.

Keep it breezy, casual, fun, and gently snarky (this applies to your profile and the intro letter). Something like,

"Hey, looks like we're both into [whatever in her profile made you go a-flutter, then maybe elaborate *a bit* on why you're down with the same whatever]. That's great! I think there's a chance we could get on pretty well. Let me know if you'd like to chat a bit more. Thanks!"

As far as the profile goes, I've noticed two archetypes: the lecherous macho dude (he's the one that sends the form letters to anybody who looks like she might be a nice piece of tail), and the sensitive intellectual wanker. This is the guy who makes it a point to *not* be the lecherous macho dude, and takes pains in his profile to appear smart and sensitive, which just comes off as boring and takes-himself-too-seriously like. A dating site is the last place you want to overthink a plate of beans.

So: keep it simple, and have fun with it! A non-response isn't a rejection; women get spammed with so much creepy shit that it's honestly hard to seperate the wheat from the chaff, as it were.

Oh, lastly: for the love of god, put a picture in your profile. If it's not there, you're going to be labeled as either lazy or ugly, which aren't so great for attracting your hunnybunny sweetie-pie.
posted by driant at 4:02 PM on May 1, 2007

As far as the profile goes, I've noticed two archetypes: the lecherous macho dude ... and the sensitive intellectual wanker ... A dating site is the last place you want to overthink a plate of beans.

I dunno, I pretty much only date sensitive intellectual wankers.

just be yourself.
posted by mdn at 4:32 PM on May 1, 2007

csg77: "It will seem counter-intuitive, but it is also a bonus to be a little bit arrogant. Something like - "your profile was interesting, but I still don't feel I know you - tell me why I should spend my time chatting to you - what makes you special". This positions you as a guy who has plenty of girls to talk to, and only wants to deal with the special ones."

Eeeeek! no no no no no! I have never replied to messages like that. (I've received many of them from Craigslist.) If you're emailing me, it's your job to introduce yourself, not to challenge me, make demands, or otherwise put the ball in my court immediately.

The briefer the message the better -- that said, never just say "Add me on MSN" or whatever. I don't have time to IM with every person who demanded it.

Just be cool. Be casual. "Looking forward to hearing from you" sounds like the closing of a cover letter. What you want to get across is that you liked her profile and would like to chat more... not that you're applying for a job.
posted by loiseau at 9:56 PM on May 1, 2007

Don't ask her to read your profile -- she either will or won't.
Don't say "I read your profile/your profile is interesting" -- because, duh, obviously you did or why would you be writing.
Mention something she said in her profile to *prove* you read it and ask a question.
Spell properly. Good grammar. Write it in MS Word and paste it into the message window.
Understand that women have to deal with all manner of stupid, pointless messages from men on these sites. It is exhausting and in general, women are wary.
And, for the love of god, don't sign off with 'later cutie' to a girl you have never met. (This happened to me a few weeks ago. I marvel at the cluelessness.)
posted by gsh at 5:34 AM on May 2, 2007

Sometimes it seems like you need to hit a home run in the opening email, but if she just looks at your profile and goes "meh" when she sees the photos, it's going to get deleted.

I'm in the same boat. It seems like half the women on Match.com have read "5 people you meet in heaven" (3 years ago it was "DaVinci Code") and they all wanto hike the Maccu Picchu trail in Peru. They're probably bait profiles.

Just be yoursely. Say something witty. Comment on something in the profile.

And be prepared for lots of unanswered emails.
posted by drstein at 7:04 PM on May 2, 2007