How Many Emails Before We Date?

Writing emails is hard.

I’ve been getting this message a lot lately, in response to a first email. I think it’s becoming a trend.

“Thanks for your note! You seem really cool. Wanna grab a drink? I’m more for meeting in person than trading lots of emails back and forth. When are you free?”

And you know what I do then? I hit delete.

Perhaps it’s thought of as progressive, as the sign of a modern dater, one who wants to eschew email chatter and head right for the first date. “Screw this small talk bullshit, let’s get right to face to face!” It’s the sort of line you’d give a brassy Kathy Bates in a movie about Internet dating, if anyone would ever cast Kathy Bates in a movie about Internet dating. It’s what people say when they’re trying to sound “no nonsense.” Unfortunately, to me all it sounds like is a waste of time.

There’s a lot to be learned on email. Can my future date write a complete sentence? Does she have anything interesting/funny/smart to say? Does she use the word “yowzers,” thereby nullifying her interesting/funny/smart-ness? And, perhaps most importantly, is she into the exchange, or do they just seem to be going through the motions? Yes, you could find all this out on a first date, but I for one would rather discover that I’m talking to a zero when I’m alone on my couch, rather than out a bar, staring said zero right in the face.

Me, basically.

Also, isn’t wanting to meet someone without communicating at all first just a little bit sketchy? Shouldn’t you be worried that I’m a zero also? Because at best, I’m like a 1, 1.5 on a good day. The whole thing just seems suspicious. And why aren’t these women more afraid for their safety? Is it that I don’t seem threatening? Because I have recently begun Kenpo Karate gym classes, and my instructor only rarely laughs at me anymore. I don’t know, I feel like meeting without emailing is a lot less like Internet dating and a lot more like kidnapping. “Hey you – random person – get in my car! We’re getting cocktails and being flirty for the next hour. Oh, and you’re paying!”

So what then should be our emailing game plan? Write and write and write, until you’re absolutely certain this person is the one for you? Nope, that’s also wrong. You know how you can miss your window with someone by going on too many dates without sealing the deal? Then, before you know it, you’re in The Friendship Zone? Well, the same thing happens with email, only it’s called The Annoying and Entirely Pointless Zone. There are people, usually men from what I’ve heard, who carry on email conversations seemingly without end. They’ll write back and forth  for weeks, sometimes months, without ever asking you out. It’s not even like they’re thinking about it, they just blabber on about their job or favorite movies, like your grandmother or something. It’s demented, and I won’t stand for it. The maximum emails one person can send in an online dating exchange is five. FIVE, folks. Any more than that and you might as well sign up for summer camp, because you’ve got a pen pal, my friend. And honestly, five is pushing it.

The ideal email exchange before asking for a date is three messages. You write her three times, she writes you back three times. On the fourth email, you ask her out for a drink. That is the exact amount of communication required to know your partner is delightful, not a psycho, and there’s a bit of juice between you. If the man or lady trails off before three emails, then they weren’t really interested. If they take longer than three emails to ask for a date then, well, they weren’t really interested. Remember, the goal here is not have to an amazing online correspondence, it’s to have an amazing first date. So leaving the other person wanting more, a little curious about you and your story is what it’s all about. Whet their appetite, reel them in, then ask to meet in person. Because, remember if they get bored, there’s plenty of suitors in their email box, waiting to take your place.

And some of them might know Kenpo too.

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25 Responses to How Many Emails Before We Date?

  1. Vanessa says:

    B – Don’t worry, guys aren’t the only ones getting these ridiculous “I’m too lazy to write so lets get a drink and be awkward at a bar,” emails. I’ve gotten them too and like you, immediately hit delete. Maybe it’s because I’m disgusted by the laziness or simply because well ya know, I value my life and time, and don’t want to meet up with Kenpo enthusiast guy. Either way, deleting is still the right decision to make.

    • BIBTD says:

      Am I a terrible person for archiving my emails? If my emails are too crazy, I used them as conversational pieces. Guess that makes me a weirdo huh?

      • I do the same thing! I keep my fb messages, too. I once got asked out in a fb message that included “I had steak. I love steak. Do you like steak?” … by the end I had no idea how to respond. He was a friend of my friend and I hardly knew him. She even suggested that I just ignore it. It’s one of a few that’s made for some good conversations with friends!

    • Sonali says:

      I’ll admit I’m that ‘crazy’ person that does that. But I rather do that than chat for weeks only to not like the person at all when I meet them. I’ve chatted and had “connections” with guys online only to meet them in person and I didn’t want to have anything to do with them after that one coffee. This has happened sooooo many times, that I’ve lost count. On the other hand the last guy I dated asked me out to dinner in the second email and we dated for 5 months and hanged out for 11 more. The reason is even though after 5 months we realized we weren’t a great match romantically, we liked each other’s company and he and I were new to the city and needed company to explore it together so it worked. I still love talking to him and we text each other the whole day. He turned out to be better looking in person than his pictures ( for some reason it makes it look like he has a pot belly when he doesn’t. weird). My BF right now is the same 2 messages and that’s it, met in person and we’ve been going out for more than 5 months. I don’t care if you can write sonnets in 3 emails. If I don’t like your company in person, those 3 emails were a waste of my time. Meet get a drink talk and if it works out go for dinner. If it doesn’t, move on.

  2. Kbizzy says:

    You’re getting weirder and weirder B. Usually guys complain about girls never wanting to meet face to face. Despite your funny tales I’m starting to think you’re your problem with this dating thing, and maybe subconsciously you really don’t want to meet anyone. It’s as I’d you’d rather have the story to tell than have something really work out.

    • B says:

      Ha ha, oh I’m definitely weird K, i wont argue with you there. But go on enough of these dates and you learn that finding people willing to meet you face to face is not too difficult. At least for me. The real trick is finding someone worth meeting. And I need to message with someone a bit before I can find out if they’re such a lady.

      • Jinggles says:

        I have to agree with Kbizzy, you seem to have commitment issues. People can project anything they want about themselves through an online dating profile, but it’s only after you meet that you see them with objectively bringing a clearer picture of who they are.

  3. John says:

    Sometimes I ask a girl out for a drink immediately, because there is absolutely nothing in her profile that I can ask her about, unless I want to know about her favorite pair of sweatpants. I’m willing to give people the benefit of the doubt that they are more enjoyable in person than they are in writing. I am the opposite, which is why I try to give women the quickest way out as possible. I also hate writing about myself in a non self-deprecating manner (this is why I suck at cover letters), however, I will talk about myself relentlessly in person. Also, I signed up for online dating to meet people and not to develop a pen pal. If I wanted a pen pal I would start writing to women’s prisons. “Dear Inmate #3654, what are you wearing? Any chance of you getting out soon? Hugs and Kisses.”

    • BIBTD says:

      Don’t force the issue. Some people are actually boring. I hate it when they say little about themselves in a conversation. Example: “So what kind of music do you like?” Girl says ” I like all music”. Then you say ” Do you have a favorite band?” and she retorts ” No, I like all music”. Forcing a conversation is the quickest way to frustration.

  4. Pingback: Word Minimum for Love « Datestable: The Subtle Art of Online Dating

  5. George says:

    John,
    If a girl has nothing in her profile to ask or talk to her about, I move on. If she can’t put in a little effort in her dating profile, which is the whole process of online dating, I move on it.

    B, ever have the long-distance messages?

    • B says:

      I’ve gotten out of city, out of state, even out of country messages. My sweet spot seems to be middle-aged Russian women who live in the middle of country. So yes, dreams do come true.

  6. SarD says:

    Every article on this blog I have read with relish (and a bit of mustard, sometimes), and almost every time I either learn something valuable and new, or I agree with the topic or viewpoint. This one, though… I have to disagree with you a little.

    My looking-for age range is, oh, 15ish higher than yours (and am certainly no spring chicken myself), and it’s not unusual at all for people in that (my) age group to be much more comfortable, in general, with in-person interactions rather than emails, messaging, or texts. A first-reply let’s-meet-in-person offer is not unusual at all. So… maybe it has a generational aspect to it.

    Also, I don’t know what your particular goal is for this process (other than “I want to find my match”), but there’s a lot of people on match and OKC that just want a bit of human contact. Every date doesn’t have to be the first step on the road to happily-ever-after. In fact, since most of them aren’t going to pan out, why not enjoy every chance you get to get out of the house and meet someone new?

    Sure, it can be cost-prohibitive if you do it too much. But have you ever been sitting home alone, thinking, “I would pay almost anything to be hanging out with someone–even a near-total stranger–doing something right now”?

    I’m of the mind that this is a much more common phenomenon than many would admit. And to avoid that, well, where’s the harm? Not like we were doing anything else anyway. Or, well, you might, being the social gadfly you are. ;)

    Anyway. Offering a bit of a different perspective. Love the blog, and keep up the good work.

  7. Datestable says:

    You’re spot on, even though I totally get where the “I didn’t sign up to find penpals” people here are coming from. Although a few of the reticent chicks I’ve met have turned out to have more than meets the eye, a lack of any conversation pieces or even mildly interesting facts in the profile is usually a good barometer of how interesting they will be in real life.

  8. Amy says:

    I know it’s sometimes hard to write about oneself. They should at least take a shot at it. And, if a guy can’t even fill out the profile halfway (and I’ve seen quite a few with all the No Preferences checked off) I’m not sure I want to meet them. That’s boring and lazy. They have to make an effort. Are they going to be boring and lazy in person? I usually roll right on by those people. Some of them might be perfectly nice people but I’ll take that gamble and keep looking for the guys who make the effort to show a bit of themselves. Only then can I know if I want to meet (or even email) them.

  9. Philip says:

    This seems counterproductive to me. Apart from your forking out for the bill sentiment, I cant see why you wouldn’t want to meet them in person ASAP. Perhaps it is because you are actually better at the email exchanges than the face to face meets? Profiles can be manipulated to achieve best results as opposed to portraying the real person, email exchanges can be crafted carefully to suit your suitor. And photos, well we all know about photos. You can argue that this (bar the photo aspect) can be manipulated in face to face meets too, but your certainly have a better shot of detecting it in person.

    I obviously have a completely different perspective to you B, but I see it along the lines of meeting someone in real life, at a club, bar, etc etc, you know nothing about that person, you meet for a date to see if you get along, have chemistry, are attracted beyond the beer goggles etc

    I also feel like this dating game is totally lopsided, men make most first contacts, and most go unanswered, anything one can do to avoid wasting time (time is money after all), seems like a wise move in my book. I also think a beer and a new face, is a better hour spent, than a email exchange.

    Set up a face to face meet in a pub, turn up 5 mins late (if you care about buying her a drink, she will have got her own by then), and explore a little.

    Also to Amy, I agree that it is lazy, but would disagree that its boring. Boring seems more aligned to a perfectly crafted profile listing all your interests and whims. But then again I’m very lazy, and incredibly boring.

  10. eric says:

    well what is the deal with a womans idea of what they want in a man these days. like almost every girls profile is the freakin same, they want a guy who is extremely good looking, rich and they will disguise that with word with words like successfull lol, athletic which is understandable no body really wants a fatty but why not someone with a few extra pounds?, funny… who the hell doesnt want someone funny?, outgoing? ok and tall, smart, ambitious, jesus people put something original or maybe reasonable? good luck finding a brad pitt look a like on an online dating site that is also all those things.

  11. innocentbystandr says:

    People… he didn’t say that you SHOULDN’T ever meet in person, just do it after 5 email exchanges. You’re acting like he said to never meet anyone ever. And frankly, 5 emails doesn’t make you a pen pal. To a lot of people, it makes you the difference between an illiterate with no personality and a decent option with brains and something to say. I think it is a personal choice whether to speed things up and skip right to the face-to-face thing, or nurture the conversation side to things for awhile. Both have their pluses and minuses equally. But I just feel like some of the comments here sound as if B is telling us to write emails for weeks on end. He isn’t. He blatantly said 5. Is 5 suddenly some astronomical number? If you’re really feelin’ someone after a couple messages, 5 will be reached very quickly. I don’t think it was meant to be taken as far as “I’m either meeting them immediately, or forming a pen pal”. I think B’s advice was somewhat of a comfortable middle ground.

  12. KevLars says:

    You need to do what you feel personally comfortable with. The minute you start analyzing how many emails you need to send before asking her out, is the minute the connection turns inorganic. “Shoot, I’d love to meet this woman for coffee, but we haven’t exchanged the appropriate amount of emails yet.” Then she’s sitting on the other end thinking, “If he doesn’t ask me out in this next email it’s over.” Lmao. If you want to ask a woman out after one email do it. If she turns you down then find a woman that will meet you after one email, and she’s probably more your speed. Analyzing, controlling, and trying to put it all into a nice neat little box just doesn’t work, cause it ain’t natural yo!

  13. TJ says:

    Having been doing this online dating thing off and on for years, there is one thing I learned. Everyone is just weird. One person wants to meet right away, another person wants to email and be a Pen Pal for 5 months before they decide on meeting! WTF. So we exchange a few emails with a new match and ask her out for a drink and then she gets creeped out and hits DELETE? Really? So we are supposed to be mind readers and know when the “perfect time” to ask you out is? This whole thing is beyond ridiculous if you ask me.

    I had one match respond to my email with her phone number, she said she wants to meet potential matches right away as she does not like the whole emailing back and forth. I accepted and we went on a few dates. It was refreshing. Even though it didn’t work out, it was nice and I was open to it. Should I of hit DELETE? No wonder there are so many single women out there with lots of cats.

    • mike says:

      Well said. If you want a girl.Its Better to only be lookin for sex to begin with honestly as a dude. Relationships happen that way. If thats what you want. Be the guy every women complains about and soon enough you’ll be married. Being concerned about a womans one thing one minute another the next, emotionional roll coaster, wants a good boy with a bad boy attidude??? Reads to many romance novels and magazines and has a tmz driven crazy every man should have a crystal ball mind.. is pointless!! Just F them good treat em right try your best to listen to them lol. And live your life the way you want

  14. Giovanni says:

    How about if when the guy asks the girl out right away, the girl can tell him she’s uncomfortable with idea of meeting too soon, but she might if he tells her about himself and if they get along. A smart, faithful guy that isn’t good at dating will be happy to do so, or at least try, while the uninterested and strange guys won’t. Not all guys know how to date, it’s not like somebody teaches us how.

  15. Avrohom says:

    Why all this talk of typing, it’s 2013 WE HAVE PHONES?! You could have typed 120 years ago by tele typing!

  16. Jim says:

    Have you eve thought communication isn’t just words, it’s gestures, facial expressions, body movements that help to fully .communicate a point? I’m disgusted that the human race has succumb to this divisible form of communication.

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