How to write opening emails on online dating sites.
January 28, 2008 11:28 AM   Subscribe

How to send that first email in the world of online dating.

So I'm on a few online dating sites. I'm a paying user, and I've got a profile up on okcupid as well. I haven't been living in the area I'm living in for long, so I don't know many people.

I'm looking for tips on how to approach that first email to a woman. I'm a man, fyi. I am not really a serial dater; I'm interested in something that could lead to a relationship. I'm old enough that I am interested in settling down with the right person.

But I never know how to open. I've read some other AskMe threads about online dating, but I'd love to hear about techniques that have been effective for you. Or, if you're female, what helps a message to you stand out from the crowd?
posted by anonymous to Human Relations (47 answers total) 52 users marked this as a favorite
I've never done any online dating before, but something along the lines of:

"Hi, you look like an interesting individual. I was wondering if you wanted to go out or talk sometime, I think your interests as well as mine match pretty well."

Could work. Obviously it's to short but I leave it up to your imagination to feel the gap.

Just remember the key: interests, interests, interests. In most of my past relationships the women I ended up being more compatible with interest wise have always benefited in the long run. Your mileage may vary...

Good luck, let me know how it goes, those online sites have always intrigued me.
posted by Schuby at 11:34 AM on January 28, 2008

Don't invest too much in the first e-mail because if you do, you will be refreshing your inbox every few minutes and that is an emotional freak out you don't need. An emotional freak out you don't need especially if you let it show in the second e-mail if you get a reply back.
posted by spec80 at 11:43 AM on January 28, 2008 [1 favorite]

Well, I tend to use the non-sequitur approach. It doesn't always work, but sometimes it does.

You've got to know to read people. It's much harder from text-based profiles than in person. I try to construct what I think this person might be like in real life, based on the limited bit of info (which may or may not be true) on their profile. Extrapolate patterns, e.g. She likes knitting, and I have a friend who knits, so she may have similar likes/dislikes to my friend. Or not. But sometimes this line of thinking helps.

Once you figure out what sort of approach a particular person would likely respond to, you decide if you're comfortable saying that. If the person is arty, and you like art, talk about art. If the person is into sports and you're not, then don't pretend you are.

Or, as I said, you could take my approach, and talk about squirrels and cowardice and see if they write back.
posted by kpmcguire at 11:45 AM on January 28, 2008 [1 favorite]

for your message, say something specific about their profile (especially if it's a little witty) and ask a question.

as for the profile, have friend (better if they're a girl!) look over it to make sure it reflects well on you. don't bother including negatives (i'm not looking for blablabla), instead focus on positive stuff.
posted by noloveforned at 11:46 AM on January 28, 2008

I've done a lot of this. (I'm now in a relationship, but not one that was initiated online.) I would look for females (I'm male) in my chosen age group who had interesting profiles in terms of my own pastimes, then I'd fire off something brief and chatty, just a couple of paragraphs, referencing the shared interest. "I do some gourmet cooking too -- what sort of olive oil do you like best?" Or "I see you like Kubrick's films -- did you see that post on MeFi about the comment tracks for the re-release of Clockwork Orange?" Or some such.

The thing about the whole online dating world is that of ten contacts you email out, one will respond negatively ("Thanks but you're not a good match for me."), one will reply positively ("Oh, I didn't see that about Clockwork -- got a URL?") and eight will simply ignore you. I conducted that experiment at least three times. It's annoying, but there it is... you wouldn't have wanted to have dealings with those ill-mannered ladies anyway.

One word of advice: have a nice picture of yourself to post. Get a photo-savvy friend to take it if all you have is the usual face-forward driver's license shot.
posted by Guy_Inamonkeysuit at 11:50 AM on January 28, 2008 [1 favorite]

One thing that I always did was ask a question about something in the photo provided. For example, "Gee, that's a nice boat you're standing on in your profile photo. Where was the picture taken?" It's a great opener, because you're asking the other person about themselves, but not in a creepy way. All it shows is interest without making you look desperate or wierd.

The other thing I used to do was to email a guy (I'm a girl), and just flat-out tell him what I liked about his profile.

Good luck!
posted by LN at 11:52 AM on January 28, 2008

Keep in simple. Don't go out of your way to sound "unique" unless you're actually a good writer, as it will probably sound forced otherwise. As long as it's more cogent than "ur hott, i lik ur boobs ... want to get drinks l8r???" you're probably going to be fine. Be conversational and personable, and mention something unique about her posting (so she knows you're not just casting a wide net).

Regardless of how you feel you look, include a picture on your profile. Doing so increases the chance of you getting a response more than anything else. But yea, make sure it's not a picture of your junk (sounds obvious, but you'd be surprised at how many people don't follow that rule).
posted by Nelsormensch at 11:52 AM on January 28, 2008

I had great success dating online, with a number of relationships and friendships as a result. The best first emails I got were, in order of importance to me:

1) well-written and grammatically correct;
2) clearly written to me, responding to my profile;
3) funny, witty or thoughtful, and;
4) brief.

All the big stuff (looking for a serious relationship, location preferences, religion, etc) should either be in your profile already, or saved for a later conversation.

A letter I pulled out of my archives that I thought was a wonderful first contact (greetings and usernames/links to profile deleted, of course).

"I like the way you put words together. Your appreciation for Iris Murdoch and architectural details is rather appealing as well. (Not to mention your lovely eyes.) I'm guessing there's a good chance we might find each other entertaining.

Care to continue?"
posted by minervous at 11:52 AM on January 28, 2008 [3 favorites]

Pay attention to your spelling and grammar.
posted by amro at 11:54 AM on January 28, 2008 [3 favorites]

"Hi, you look like an interesting individual. I was wondering if you wanted to go out or talk sometime, I think your interests as well as mine match pretty well."

As a woman who did a lot of online dating and is about to married to a man she met online, I'd have to say that that's the worst thing you could have opened with to me.

What was key to establishing a rapport with someone was that they wrote to me and indicated that they actually read my ad AND has some affinity for it. If I mentioned a particular film I loved, then a good response would be: "I see you liked Punch Drunk Love. That's one of my favorite films, too. Did you like any of P.T. Anderson's other films?" The key to that sort of response was that they obviously read my ad and related to it and then they asked a question that started a dialogue. If you just say "Hi, you sound interesting" then what do I have to respond to?

If you notice that she mentions a place, a hobby, a certain perspective that you share, then mention it in your initial response and give her something to respond back to you with.

And don't open with "do you want to go out sometime." Those guys just seemed like they wanted to be on a date, any date, in order to score and made me nervous. I wanted to know more about someone and see how much they were interested in knowing me before I'd go out with them.

The guy that I ended up with did exactly this. In fact, he wasn't very close to my stated target demographic but because he continued to offer a chance for conversation and interaction by seeming genuinely interested in me and telling me some very specific things about himself that I could relate to, I was interested in meeting him. And so we met and a year later got engaged.
posted by otherwordlyglow at 11:55 AM on January 28, 2008 [11 favorites]

Disclaimer: I'm a gay man. It may be a bit different etiquette wise, but we do a lot of online dating.

I just send a "Hey there, how's it going?" If their profile particularly strikes me, I may add an extra sentence. They're not judging you on your message anyway, it's just a way to get them to look at your profile. If they like what they see there, they'll get back to you.
posted by awesomebrad at 11:55 AM on January 28, 2008

The best way to open an email to a stranger is a compliment in the subject line (so she will definitely open it) and a question about one of her interests, hobbies, or photos inside the body of the email.

Anything you have in common, remark on; "We both love pugs!" "I have a sister who runs marathons, too!" "My dad was also a preacher, but we lived in West Virginia..." Tell her some things about you that aren't in your profile, and make sure to check grammar and spelling before sending.

Make it short and sweet; if you email back and forth three times successfully, call her and speak to her on the phone. If the phone call goes well, meet for coffee. That's the short and sweet of it right there. Make the coffee date for a time where, if things go well, you can carry on to the movies, dinner, a drink, or other activity (or on a day like a Thursday, so you have the weekend together if it goes well, or a Sunday, so if it doesn't go well, you have the rest of the week to look for other potential dates).

Do NOT make your emails generic; always reference specifics about the lady in question so she knows you're not a spammer or serial e-mailer.

A few articles you may find helpful:

What the first email reveals

Send a standout email

What makes an irresistible email
posted by Unicorn on the cob at 12:04 PM on January 28, 2008 [1 favorite]

As a woman who did a lot of online dating and is about to married to a man she met online, I'd have to say that that's the worst thing you could have opened with to me.

Well as I said I've never had to shatter the ice via the internet, let alone a letter of some sort.

But in my defense I said it was obviously to short and needed filler. I agree with you 100% though, specific interests and points make it personal and more appealing.

When I confront people in real life, I always open with something witty like"hey, want to buy me a drink?" (only works if you are a male talking to a female). It's never serious, just a jump start for a conversation.
posted by Schuby at 12:06 PM on January 28, 2008

I've used various approaches with success:

1. Short but to the point... I've sent entire emails that consist of "Drink?" or "We should meet." They work more often than not, but mostly it depends on your and her profiles and the type of people you are.

2. Target something specific that you like in her profile. That is, if she mentions a book or film or something that you've got a similar opinion on, send an email like, "Hi--just noticed that you're also a fan of The Dying Animal, which happens to be my favorite book. What did you like best about it. Please take a swing by my profile and if you like what you read, get back to me and we'll take it from there."

3. If there's nothing to grab onto in the profile but you want to write anyway, try some Q&A combined with a bit of self-deprecation: "Hi, I'm itching to write but suck at these break-the-ice emails... so I'll just cut the to the chase: i) cake or pie? ii) last time you bust a gut laughing and why? iii) what's something you refuse to put in your mouth? iv) what's your poison? v) favorite word that starts with G?"

I've had the most success with 1 and 3.

My best advice is to make sure you ask a question in your email. That is, give her something to write you back about. I can't count the number of emails I've gotten on the personals where the person just tells me about themselves or what they think of my profile but they don't actually say anything that I can comment on so all that does is put the ball in my court to come up with a break the ice letter of my own and unless your profile is stellar, that's probably not gonna happen.
posted by dobbs at 12:12 PM on January 28, 2008 [2 favorites]

I'd like to respectfully disagree with the first answerer: please do not feel the gap. It almost certainly leads to no good on a first date.
posted by AwkwardPause at 12:13 PM on January 28, 2008 [1 favorite]

I cannot begin to emphasize the necessity of spell and grammar checking your email. Also, it's not a bad bit of habit to write a draft, get away from it for an hour or so and then come back and read it again.

And don't take it personally if the woman doesn't reply.
posted by gsh at 12:13 PM on January 28, 2008

Oops, that should be "What did you like best about it?" Watch the grammar. :)
posted by dobbs at 12:14 PM on January 28, 2008

I met my boyfriend of over 3 years on OkCupid. When I was doing the online dating thing, I tended to immediately reject e-mails that were:

* generic. Anything that sounded canned or did not directly respond to something in my profile was chucked
* accompanied by cock shots. For obvious reasons (or perhaps not so obvious? Some online daters seem to have a hard time with that).
* poorly spelled or otherwise indicative of atrocious grammar or command of the English language (very important for this nerdy bibliophile)
* aggressive, desperate or rude

E-mails that caused me to look twice referred specifically to my interests, showed curiosity and personality, and did not come on too strong. Humor always helps, as does politeness.
posted by mynameisluka at 12:16 PM on January 28, 2008 [2 favorites]

Oh, and this isn't directly related to your Q but... not sure what happened with it but you should be aware that was sued a few years ago when it was revealed they were paying women to wink (or whatever their equiv is) at men in order to get them to spend the credits to make contact.
posted by dobbs at 12:18 PM on January 28, 2008

I agree with just about everything above. My advice:

-Definitely use good grammar and capitalization. You don't have to worry about whether your participles are dangling (heh); writing like you did in your question is fine.

-Aim for about three to six sentences in the first email. Too long and you run the risk of looking clingy or creepy. Too short and you'll come across as lazy and generic.

-Guy_inamonkeysuit, minervous, and otherworldlyglow have pretty much nailed it: reference something in her profile that interested you, and use it to start a conversation. Try not to use the most obvious conversation starter in her profile (e.g. "the most private thing I'm willing to admit" and similar questions) because she's already heard it twenty times. Including a specific but open-ended question is a good way to get a response.

-Don't put "hello" or any variation as your subject line, or "very interesting profile," or "I like your ____," or leave it blank. Most guys do this. Just about anything else is better.

-As tempting as it might be, don't say too much about her looks. If she has a photo up and you're messaging her, it's pretty much a given that you find her attractive. If she's conventionally attractive, it's been in every single other email she's received. If she's not as conventionally attractive, she may be worried that you won't find her as attractive if you meet in person (and you might not). Some compliments are fine, but be more interested in her personality than her looks.

-Also, be more interested in her than in a relationship. You mention that you're interested in a relationship and "settling down" -- if you find the right person, that will happen eventually anyway. If you talk too much about your goals for a relationship, you might come across as desperate.

-In my experience, if you click with someone, you email for a few days to a week before meeting in person. I'd recommend developing a rapport before suggesting an actual date.

-Don't get frustrated if not everyone writes you back, because they won't all write you back. There's nothing less attractive than a guy whining on his blog about how no one ever responds to his emails.

Good luck!
posted by Metroid Baby at 12:28 PM on January 28, 2008 [3 favorites]

I'm going to respectfully disagree with awesomebrad. It seems to me that his suggestions match how men prefer to interact online, which is obviously fine if you're a gay man, less good if you're heterosexual.

I'm a straight man, I've spent a fair bit of time on online dating sites, and the impression I get from women on those sites is that the following, as posted by minervous, are good approaches

1) well-written and grammatically correct;
2) clearly written to me, responding to my profile;
3) funny, witty or thoughtful, and;
4) brief.

Less good:

1. Penis photos (I've seen many many women explicitly ask not to receive these)
2. One sentence messages ("Hi, wanna meet up?")
3. Messages that show you clearly haven't read their profile, or that are obviously being cut and pasted to dozens of women.

Further (unsolicited) advice:

1. Get used to disappointment. There are usually more men than women on these sites, and a lot of men are messaging a lot of women. Your message is one of many, and statistically will probably be ignored.
2. I personally got my best results from women contacting me, not vice versa. So make your profile as good as you can make it, and maybe they will come to you (then again, I'm not American, it may be different in your country).

Good luck.
posted by Infinite Jest at 12:38 PM on January 28, 2008

No offense to Schuby, but:

Hi, you look like an interesting individual.
Hello, I see that you are a female.

I was wondering if
It occurred to me that maybe *looks down sheepishly*,

you wanted to go out or talk sometime,
If you were interested in talking to me oh god oh god please,

I think your interests as well as mine match pretty well.
We could discuss how compatible we are. Our Internet summaries appear to match.

Don't: Be indecisive, ask for a date, or say you're compatible.

Do: Actively try to start up a conversation that both of you can contribute to somehow; find something low-pressure that you would both enjoy, without playing e-mail ping-pong or pushing it in the opening volley ("Hey, since you're into THING, there's a THING exhibit at the MoMa next week that looked great. Let's check it out, if you're down."); and remember that Internet profiles are Cliff Notes, and that you won't know if you're compatible until you actually find out.
posted by Mikey-San at 12:42 PM on January 28, 2008 [1 favorite]

Also, be more interested in her than in a relationship. You mention that you're interested in a relationship and "settling down" -- if you find the right person, that will happen eventually anyway. If you talk too much about your goals for a relationship, you might come across as desperate.

Totally on the nail. Personal ads are all about SHORT-TERM GOALS, regardless of what anyone puts in their profiles regarding what kind of relationship they're seeking. Why? Because the personal itself is informal and brief; it's the first short step to the next short step (the introduction). That leads to the next short step (talking to find out if a date might be fun), which leads to the next short step (the date itself), and so on.

First step, show that you are interested in the person. Relationships happen or they don't. Not your concern.

In my experience, if you click with someone, you email for a few days to a week before meeting in person. I'd recommend developing a rapport before suggesting an actual date.

More solid gold here. Don't open with the date, but don't go back and forth forever. Either you want to meet at some point or you don't, right? See if you're on the same wavelength, then suggest something fun to move on to the next short step.
posted by Mikey-San at 12:49 PM on January 28, 2008 [2 favorites]

I met my now-fiancé online. His e-mail was short and simple (paraphrasing): "Hi, I saw your profile and you seem like an interesting person. I live in ____ and work in the _____ industry. On the weekends I like to hike and take pictures. I'm ideally looking for a long-term relationship but I can always use more friends. Take a look at my profile and let me know if you're interested in chatting further."

Why did it get my attention?

- it wasn't desperate-sounding (anything over 2 paragraphs seems to scream desperation for a first contact)
- he didn't pressure me at all - the next step is up to me.
- it didn't mention sex AT ALL, nor insinuate it. I'm not dumb, if you're looking for a relationship then I assume you'll eventually want to have sex with that person. But unless you're looking for sex Right Now, don't mention it.
- it told me some brief, specific facts about him that might rule him in or out depending on what I'm looking for. If his hobby is World of Warcraft, we're probably not a match.
- he's not bragging or trying to impress by claiming he scaled Everest or some such BS. If you have, in fact, scaled Everest or won the Nobel Prize, don't mention it in the very first e-mail.
- he paid basic attention to grammar and spelling, which 90% of male respondents to dating profiles do not do (seriously, if you can write a decent sentence, you're already far above most guys online).

I replied with something to the effect of "Sure, let's chat sometime," and his second email included his real name, phone number, and the best time to call. He also included some photos of himself engaged in his hobbies (rather than him obviously trying to look sexy).
posted by desjardins at 12:50 PM on January 28, 2008 [1 favorite]

Be funny, articulate, polite and confident. It works online and off. Additionally:

Don't make her looks the first thing you mention.
Don't tell her you're looking to settle down just yet.
Don't tell her anything about what you're looking for "in a woman" like she's a Toyota.
In your efforts to be funny, don't resort to juvenile epithets such as "It was so retarded" and "That is so gay"
Spell yer grammar good.
Leave. Your penis. Out of it.
Don't tell her you're new to this and you're only on the site for laughs and/or because you're sick of "the bar scene."
May "let's see where it goes..." be stricken from your typing fingers.
Quoting movies can be an icebreaker, but not if it's Silence of the Lambs. Save that one until you know her better.
Don't stress over it. This is supposed to be fun for all involved. If your first e-mail is too carefully composed, it's going to show like the trembling hands of a nervous dork.
posted by katillathehun at 12:57 PM on January 28, 2008 [1 favorite]

Dobbs, I can authoritatively answer that your assertion about the winks and the paying is not true. I ought to know; you can memail me if you'd like to discuss it further.

All online dating sites get sued routinely for various things; however, none of these lawsuits have come to anything, as they are almost 100% overturned due to lack of evidence.

Carry on!
posted by Unicorn on the cob at 12:57 PM on January 28, 2008 [1 favorite]

Oh, also, under no circumstances should your profile picture be of you playing a guitar. Or standing next to your car. Those are instant deletions. And if it's taken inside your house/bedroom/office, be sure whatever is in the shot is presentable, clean, and neutral.
posted by otherwordlyglow at 1:26 PM on January 28, 2008

Oh, also, under no circumstances should your profile picture be of you playing a guitar.

The exception to this is if you're rocking the fuck out on stage with your band and someone took the picture from the audience! (And you don't look like a pompous guitar masturbator.)
posted by Mikey-San at 1:32 PM on January 28, 2008

Basically, if you look like Steve Vai on stage, leave the picture out. If you look like Ted Leo, you are golden.
posted by Mikey-San at 1:34 PM on January 28, 2008

Make sure to ask a specific question related to her interests or her profile. If you just talk about yourself or write a generic "how are you?" email, there won't be anything there to latch on to or respond to.

Don't knock yourself creating the perfect most clever email ever. Keep it simple, short, and personalized to her (lots of good advice above).

Remember that your profile and pictures are just as important as the email. Spend some time on getting those right. Even the wittiest email won't mean much if you don't have an interesting profile to support it.

Think of this as a fun dating obstacle course:
When you write to a woman, she'll read your message, see your face, and then (with any luck) click on your profile to learn more about you before writing back. Those are 3 separate things she has to see and like, and any one of them can be a stumbling block. Your goal is to get her to your profile and writing back to you, so make sure each of those pieces is good enough to keep her going forward with you.

Good email = personal, short, inviting, non-presumptuous
Good pictures = at least one face shot, one full body (fully clothed) shot, you should be smiling and look happy in at least one
Good profile = real answers about you, a little humor, reflects your personality as well as your interests
posted by rmless at 1:37 PM on January 28, 2008 [1 favorite]

One more on the photo: Please do not put up a photo of you and a woman and just chop her out of the photo. Every time I have seen a photo cropped too close on one side, and a strange female arm coming out of nowhere, I have quickly moved on.
posted by Vaike at 2:01 PM on January 28, 2008 [1 favorite]

Nthing the advice to ask her a question about something in her profile. Something like "I find you interesting" makes her do the work to start the conversation--she has to figure out what it is that you might have in common. Make it easy for her to respond by giving her something specific to respond to.
posted by donajo at 2:04 PM on January 28, 2008

One more on the photo: Please do not put up a photo of you and a woman and just chop her out of the photo. Every time I have seen a photo cropped too close on one side, and a strange female arm coming out of nowhere, I have quickly moved on.

YES. Never ever do this. I'd go a little further with this and advise that all your photos be of you only. It doesn't matter whether the other person in your photo is a Playmate or your eight drinking buddies or your infant daughter or Kofi Annan. The purpose of the picture is so women can see what you look like; it's better to leave the rest to your written profile. (Group shots are often blurrier and less flattering than individual photos.)
posted by Metroid Baby at 2:20 PM on January 28, 2008 [2 favorites]

A lot of really good advice in this thread so far. Here's my perspective:

Avoid anything that sounds like spam. "Hi, I'm X and loved your profile, you should see mine." Keep it short. 2 small paragraphs is almost too big. Don't talk about attraction. If they seem real, pick one or two things that stood out to you and discuss them, or disagree, etc. "I like Nick Hornsby too but I thought About a Boy was total dross, why do you like it?"

If someone's profile seems too good to be true but you're still interested in them, mock them. This is good because these are the women that every other guy has e-mailed and they're all falling over themselves to compliment the girl; distinguish yourself by asking if that picture is actually of her mom. In the same vein, feel free to accuse her of actually being a man, or having horrible grammar or vapid interests, etc.

Be witty. Make her laugh. Ask her a question or two so she knows what to say in the reply. Don't tell her what you do for a living or where you live in the first e-mail. Keep some mystery so she wants to write you back. Oh, and unless you are very, very attractive or very, very confident, don't be self effacing. You're not likely to be written back if you've already started issuing disclaimers.
posted by Happydaz at 2:32 PM on January 28, 2008 [1 favorite]

One more on the photo: Please do not put up a photo of you and a woman and just chop her out of the photo. Every time I have seen a photo cropped too close on one side, and a strange female arm coming out of nowhere, I have quickly moved on.

Associating with women is bad? Really?
posted by MillMan at 2:55 PM on January 28, 2008

Associating with women is bad? Really?

Guys typically do it when the other person was a previous significant other. To women, it gives the impression of potential bitterness and raises the thought of "Do you really not have a photo of yourself that shows you exist on your own?"
posted by Mikey-San at 2:58 PM on January 28, 2008

If someone's profile seems too good to be true but you're still interested in them, mock them.

Good advice, although it's a subtle art, and it will fail repeatedly until you figure out how to do it correctly.
posted by MillMan at 2:59 PM on January 28, 2008

Agreeing to say do show that you have at least read their profile, and you're not just sending the same email to 100 other women. But don't overdo it. Funny is good, but be gentle...and don't try to hard to show how smart or funny you are. Trying too hard has an unmistakable smell to it.

Personally, I have been more open to people who are straightforward and say what they want, e.g., "I like your take on the politics of mountain climbing; want to discuss over coffee?" If you don't want to go right for a date, ask them about their interests that you share with them, referencing a movie or a book and asking if they saw/read the most recent thing by that director/author, and what did they think of it, for example.

Us girls love compliments but that can be dangerous territory, so check with a female friend to make sure you're going about it the right way. Be sincere and light...yeah, we know boys like boobs, you don't have to actually say that.

Send out a lot of emails just to get comfortable with the process and to see what kind of feedback you get from your efforts. You will find it easier to hone your emailing skills with all that practice.

In the end, no matter how good your email is, if they aren't into you, they just aren't into you. When I get emails from someone I am just not into, I really don't know how to reply in a non-hurtful way (maybe the subject of a future question here!) and thus don't reply; I imagine a lot of women are like that, so don't get too hung up on one email that you sent or the lack of replies.

Good luck!
posted by kenzi23 at 4:21 PM on January 28, 2008

My name's ____ and I'm responding to your ad on You seem really nice. [Insert something specific you liked about her profile.] I'd love to get to know each other a little better. If you're interested, I hope to hear from you soon. Have a nice day!

p.s. [Insert question for her.]

Notice several things. 1. You say your name. This shows you are being upfront and honest, and not a stalker. 2. You compliment her, without swooning. I think "nice" does the job nicely. 3. You say something about her profile- not about her looks. 4. You use the word "love" in a subliminal message sort of way. Others may disagree. 5. You say "If you're interested..." because it makes it seem like you're not desperate. 6. You tell her to have a nice day, and use an exclamation point, to show you're not depressed. 7. You include a question as a p.s. to give her something to talk about in her reply.

I would strongly recommend against trying to be clever in your first email. I did that for a while, then I figured out it's just a waste of time, since so few girls respond. This form email is better, I think. (though to be honest, it hasn't worked for me...)
posted by proj08 at 4:25 PM on January 28, 2008

"I am not really a serial dater; I'm interested in something that could lead to a relationship. I'm old enough that I am interested in settling down with the right person."

That is the exact wrong attitude for the online dating world, in my experience. The phrase "settling down" means "settling for", and that's not a positive. And neither is "looking for a relationship". What that reads as is "I'm totally desperate and will do whatever you say." At least in most circumstances.

The above advice is all good. Especially the good grammar, low key, positive, bright and short advice. Pretend this is a person you met waiting in line somewhere. "Oh, you like puppies? Me too! What kind do you have?" or "Hey, nice Favre jersey! It's a shame they didn't make it to the big dance."

You are selling yourself by not selling yourself, by just being likeable. If you try to game the system, you will only attract other gamers (girls who are just there for serial dating and/or free dinners). You gotta be real in a non real environment. It's practically impossible, really.

Finally, you cannot have any expectations. First meeting really isn't even a date, it's an audition for a date. Meet for drinks or coffee, depending. "Hey, let's meet at Some Public Place for a couple brews, and see if we click in person!"

Also, be very careful with sarcasm, humor and irony on emails. What would be a hilarious joke delivered in person is a creepy non-sequiter in text.
posted by gjc at 5:23 PM on January 28, 2008 [2 favorites]

Notice several things.

Know what else I noticed? It's really scripted. Why risk the other person noticing or thinking that you're basically just sending out templates to who-knows-how-many women?

This ain't Mad Libs, people.
posted by Mikey-San at 5:34 PM on January 28, 2008

Previously, on AskMetafilter:
I need a first chance to make a first impression.

That thread begins with "What should I put in my first email to someone I found on an online dating site?" You might find some good advice in that thread, in addition to what's offered here.

There are also a bunch of other potentially useful posts tagged with onlinedating.
posted by jewishbuddha at 6:07 PM on January 28, 2008

Sorry to say, as a girl and a girl who is currently doing online dating, if I got an email like proj08 suggests, I would probably ignore it. "Nice" is kind of a veiled insult or laziness; you can say I have really nice eyes. The rest of the email just feel scripted like you sent it to 7 other women in the last hour...I guess I want to feel a little special, that something in my profile or my photo brought out something in you, made you want to say something funny or ask me a crazy question. A real name is nice, just put that at the end.
posted by kenzi23 at 6:35 PM on January 28, 2008

Don't go with anything that looks generic. Even if it is copy/paste with some modifications, it shouldn't look like it wasn't a personal effort. I immediately trashed any emails that looked like some guy was clicking through all the profiles in my zip code and spamming any girls that looked remotely attractive.

Make sure your profile (which is the first click *if* I didn't hit the delete button) is sincere. Go for amusing if you can combine sincerity and funny-ness. Don't make jokes if you just sound like some college frosh asshat fishing for dates to the Phi's house party, unless you are in fact a college asshat fishing for a date to the Phi Luau house party.

It has to look (to me) that you've spent some time on the profile and that we mesh in some way, or that you're quirky and interesting enough in ways that we aren't similar that I want to know more. If your profile is full of monosyllables, make up for it with a more lengthy email.

Don't go for "I noticed you hike. I hike too." That's pretty dull. If you can really creatively engage with her profile, you'll get noticed. For example, my (now) partner wrote this in his first response to my online profile. The profile included a category of "hottest sex in movies" and I had included the Thomas Crowne Affair. He responded:

Thomas Crowne is a favourite movie of mine, for more than just the hot sex scenes. Have you listened to the commentary? It's hysterical... the director sounds so bored talking about his movie. "Camera pan left... yup. Uhhhh, I... I think... This shot was tricky."

He built on my comment and said something pretty engaging in addition, indicating a sense of humor and some shared tastes.

He also asked a question at the end of the message- the old axiom about getting people to talk about themselves equates to them liking *you* better, he says. I say, acting like you're interested in her as well as how well you mesh with her. Either way, another piece of sage advice.
posted by arnicae at 8:48 PM on January 28, 2008 [1 favorite]

P.S. Don't mention ANYTHING about her looks. Nada. Unless you're commenting on her Persian heritage and how your uncle grew up in . . . That makes me uncomfortable and though I might not immediately discard the email, I would think you shallow and your interest in me equally insipid.
posted by arnicae at 8:50 PM on January 28, 2008

Guys typically do it when the other person was a previous significant other. To women, it gives the impression of potential bitterness and raises the thought of "Do you really not have a photo of yourself that shows you exist on your own?"

I generally take these sorts of pictures to mean that the person has no taste in photography whatsoever, or doesn't know how to operate their digital camera to take a new picture. Both of which mean "close tab, move to the next profile."
posted by kpmcguire at 1:35 PM on January 29, 2008

i got this list off a david de angelo dvd

#dont give a bunch of physical complements
#dont offer to take her out, give her a gift, buy her something,
#dont treat her like she's too good for you
#Stay away from the mindset of have to tempt her to respond
#Dont comment on how you seem perfect for one another because you love everything she loves and you have everything in common ~ sounds like trying too hard
#If you do like something the same, maybe tease her about it suggest she's maybe not as good/up as you
#Dont spend hours writing a 10page letter
#Do communicate total comfort with yourself, no anxiety, no self-consciousness
#Do communicate it wont affect you in any way if she doesnt respond, perhaps even slightly encourage her not to respond
e.g. if not good luck with your search (encourage them to be independent)
#Dont say, if you dont like my pictures etc, or equivalent
#Do communicate you're busy and having fun in life
#Be charming , challenging or even direct over inconsistencies in their add
#Do communicate you are in touch with the experience she's probably having in this environment
#Point out something that might be attracting a lot of unsuitable types, (be funny/charming)
#Do communicate you're a regular person, be candid, like comedians observe the moment we've all experienced
#Do communicate you're selective, have high standards and arent willing to settle. (be clear about boundaries)
posted by browolf at 4:54 AM on February 17, 2008

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