Dating Advice, Relationships

Do’s and Don’ts of Online Dating: How Not to Let Men Waste Your Time

31 Comments 15 June 2010

BadDate_400How soon should a man you’ve met on the web propose an offline get-together? Read on for advice on how not to let a man waste your time, from The Rules for Online Dating.

Ideally, you want a man to ask you out as soon as possible to move the relationship from the computer to a date. But you cannot tell him to do this or even hint it. On the other hand, you should not wait forever. We think four e-mails is enough. If, by his fourth e-mail, a man hasn’t suggested meeting, don’t e-mail him again. He may just need a “push” to ask you out — and by that, we don’t mean you should suggest to him that he ask you out. We mean you should simply drop out: Stop e-mailing him!

Most women hang in there way too long, sometimes as long as six months, waiting and hoping for a man to ask them out. We’ve heard of men who are still talking about politics, workout routines, and past relationships in their tenth e-mail. For whatever reason, they can’t get around to saying “Let’s meet” and following through with it.

Ed (Entrepreneur40) is a perfect example. He answered Suzanne’s ad (SassyGirl39) and she was thrilled, as he was not only handsome but seemed worldly as well. Never married and very particular, Ed thought Suzanne was attractive, but he was in no rush to ask her out. He asked her lots of questions, everything from the weather to hobbies and vacation spots. Suzanne was only too happy to answer every single one, all the time wondering if he was ever going to ask her out! She didn’t realize that by responding to him, she was preventing herself from getting a date.

Here are their e-mail exchanges over a period of three weeks:

Entrepreneur40: When I saw your ad, I thought, very pretty. I would have answered it sooner, but I had a top priority project to do. I’m an environmental engineer by day and an entrepreneur on the side, kind of a workaholic. Now that that’s done, I can concentrate on you. I have to say you look familiar. Where are you from?

SassyGirl39: I grew up in Buffalo, New York. I live in New Jersey now.

Entrepreneur40: You’re kidding. I went to college in Buffalo. SUNY-Buffalo. I skied there a hundred times. Worst snow storms I ever saw in my life. Do you like to ski?

SassyGirl39: I know, growing up I never took off my ski jacket and snow boots. I love to ski too. I have a ski share in Pennsylvania.

Entrepreneur40: I just got back from skiing in Italy, nothing like it. It was half business/half pleasure, two weeks. I could live there in a heartbeat. Have you been to Europe? Do you like to travel?

SassyGirl39: I lived in England on a semester abroad 20 years ago and France for work two years ago. I work in public relations for Hermes, the scarf company. But I’ve never been to Italy. Sounds wonderful, maybe someday. I love pasta, that’s for sure.

Entrepreneur40: Me too. Fettucine Alfredo is my favorite. I know this great Italian restaurant we can go to sometime. What do you like to do for fun? I’m a gambling man myself. I go to Atlantic City five times a year. Won $500 last time, but lost $1,200 the time before that, but hey, it’s a blast. I stay at lavish penthouse suites, catch a few shows, spend some play money. Have you ever been to Las Vegas? Or maybe you’re an Atlantic City girl?

SassyGirl39: I’ve been to Atlantic City twice, saw Earth, Wind, and Fire once and a comedian another time, I forget his name, maybe Don Rickles, lost $25 in the slot machine both times, walked on the boardwalk. I don’t play cards. It was fun.

This is the e-mail Suzanne should never have sent, the point at which she should have just stopped corresponding with Ed. After four e-mails, it’s time for a man to ask you out. If he wants to find out what you like to do for fun, or about your career and family, then he should ask you face-to-face on a date.

Think of four e-mails back and forth between you and a man you’ve met online as the equivalent of a half an hour talking to a guy you’ve met in a bar or a party. If, after 30 minutes, he hasn’t asked for your number, you have to look at your watch and say, “Wow, I really have to get going,” or “My ride is leaving, I have to go,” in hopes that that will prompt him to ask for your number or risk never seeing you again. If you hang out all night waiting for him to ask for your number, you won’t be a challenge and he may never ask.

All Ed really needed was a Rules-y girl who would not give him hours of time, or, in the online world, someone who would not be content chatting so easily and indefinitely. Men think when you chat with them endlessly that you will chat with anyone endlessly and that you’re probably not very discriminating. A man should have to work hard on some level to get all this information out of you. He should at least take you out on a date!

Suzanne was too available online and not a challenge, so Ed lost interest. Although he did allude to taking her out for dinner, it was more of a “bookmark,” with no definite date. He did not follow up by asking her for her number. Instead, he changed the subject and asked even more questions. Had Suzanne stopped e-mailing him, he might have thought, “She won’t e-mail me back. I guess I’ll have to make specific plans with her.” Allowing the e-mail correspondence to go beyond four e-mails ensured that Ed would get bored and Suzanne would get frustrated.

Here are the remaining e-mails between them:

Entrepreneur40: I’m going to Vegas tomorrow. I have an engineering convention there, five days, all expenses paid. Can’t wait. Need some R&R, this project was grueling. PR sounds fun. What exactly do you do?

SassyGirl39: I try to get Hermes mentioned in magazines and newspapers, deal with any disgruntled customers, you know, celebrities and royalty and such. I send actresses and VIPs free samples hoping they will wear them in their next movie, that kind of thing. Can’t complain. I have like 100 Hermes scarves in my closet.

Entrepreneur40: Sounds neat. Do you like sports? I’m a sports fanatic. Basketball, baseball, football, I watch sports all the time. ESPN is my middle name. I also go to the gym, run three miles a day.

SassyGirl39: Wow! Very impressive. I ski, play tennis, and take kick-boxing classes at the gym. I have two brothers so I know all about sports.

Entrepreneur40: Are you close? I’m an only child. Wish I had siblings, but my father died when I was three. So it was just me and my mother. She never remarried, she just couldn’t get over my father’s death. He was killed in a car accident on his way home from work. There were a dozen roses on the seat next to him that he was going to give her that night. They were so in love.

SassyGirl39: Sorry about your father. Must have been hard growing up without one. My dad died last year at the age of 69.

Entrepreneur40: Sorry. So, I guess I should ask the obvious question. Why is a pretty girl like you never married?

SassyGirl39: Good question…I guess I haven’t met the right one. What about you?

Entrepreneur40: Obsessed with work my whole life, I support my mother, we’re very close, and I just never made dating a priority, until now. Determined to change all that. Want to get married and have kids, more than one!

SassyGirl39: Sounds good. I always wanted to have two, a boy and a girl.

Entrepreneur40: Well, it’s late and I have to pack for Vegas. Have a 8 A.M. flight and then when I get back I have to put my mother in a nursing home. She’s 80 and getting worse and worse. I’ll be in touch.

SassyGirl39: Hope you have a fun trip and good luck with your mom. Bye!

Ed e-mailed her a week later about his trip to Vegas (he won $700 at blackjack), and about his mother’s declining health, but he still didn’t ask for Suzanne’s number. She e-mailed him back, and then he poofed! She never heard from him again.

We are not surprised. When a man takes more than four e-mails to ask you out, it is not a good sign. Sometimes he may need a push — the one girl who is too busy to e-mail him back forever. That is the one he will pursue.

Unfortunately, most women continue e-mailing men after four exchanges, often wasting weeks or months with these men. Rules girls don’t; they set limits. Of course, we don’t tell men what these limits are, we just stop e-mailing them back after four exchanges. We do not say, “We’ve been chatting for a while, do you want to meet or are you just going to waste my time?” or even the more subtle but equally manipulative, “I’m not big on e-mailing, I’m better in person,” in hopes that he will ask you out, or even “My nails break when I type…” Hint, hint!

As we’ve said before, breaking one Rule leads to breaking another. Women who continue to chat past the fourth e-mail usually end up volunteering their phone number, in the hope that it will lead to a date. They usually end up frustrated by these men anyway. These men don’t call regularly, they ask them out at the last minute, or they find trivial excuses to break up — one man broke up with a woman because they couldn’t agree on what movie to see on their third date, which led to a fight. In plain English, they break up with you because they weren’t that interested to begin with.

So if you keep writing a man back after he hasn’t asked to meet by his fourth e-mail, you are asking for trouble down the road. He may get to know you so well online that his desire to meet you evaporates (poof!). In the online world, as in real life, familiarity breeds contempt. Just cut your losses, delete/next! and move on. Of course, if after you stop e-mailing him, he e-mails you that he wants to meet you and actually asks you out, you can go out with him. Sometimes a man won’t get serious unless he realizes that you have moved on!

The Rules for Online Dating

The Rules for Online Dating

Ellen Fein


We are wives, mothers, co-authors, dating coaches, and have been best friends for the last 30 years. We came up with the idea for a self-help dating book called The Rules after many, many dinners with single girlfriends at the now-defunct Sung Chu Mein, a Chinese restaurant on the Upper East Side in New York City—it was sort of like Sex and the City, but before Sex and the City! Like most women our age, we were career-minded with our own apartments, but we also wanted to get married. So over fried tofu and mixed vegetables, we each brought our dating problems to the table. We began to notice that the women who played hard to get, either deliberately or by accident, were the ones who got the guys, while the women who asked guys out or were too available were the ones who got dumped. We put two and two together, and wrote and wrote, and that’s how The Rules were born! We had no idea The Rules would become a bestseller… we just wanted to help women stop making mistakes and get the men of their dreams—and that’s what we still do now, 20 years later! Today, Ellen is married with two children and lives in New York, and Sherrie is married with a teenage daughter and lives in New Jersey. We did The Rules, wrote The Rules, and have helped millions of women do The Rules, too. Now, we want to help you!

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  • Inna

    Great, but what advice do you give when this man is on the other side of the world?…

  • sammy

    Ohh wish I had known this earlier…I’m up to message #10! But its shown me that I’m actually more keen to meet people than chit-chat with them online. Now I know who will be the chatty ‘friends’ wanting you to fill in a gap for abit and who will be the dates.

  • Studmachine

    Don’t take them out to dinner either.

  • JustSayin

    Are women supposed to wait for a guy to ask them out? Seems a bit out-dated to me.

  • Flower White

    Yes. The man asks the woman out if not, how do you know if he truly likes you?

    Lazy, horny and crazy men want a woman to chase them, men who don’t want a serious relationship men who fly by the seat of their pants. Many men are content to waste women’s precious time. Those men don’t pursue or ask you for dates. Like lazy lions they wait for the meat to be delivered.

    Ladies don’t buy that “I’m shy” routine, that is a pack of nonsense, a dog is never too shy to hunt, so to speak.

  • macydee

    This all sounds too familiar. I have been on and off of dating sites since 2004. Most men just want to be a penpal or brag about themselves. It has replaced the bar scene and if they do want to meet, they just want one thing. This is my experience, the best advice i can give, after a couple of emails, I give them my number or I get their number. I can tell within 2 minutes if I want to meet them~ I have hung up on a few!

  • sunshine pris tymow

    oh gosh i should have known this before i got my self in a hurting relationship i was are dogs no one of them is perfect but why?

  • sally

    Iv been talking to this guy online for two weeks and after we exchanged 20 mails he told me he would like to meet me after two months because he want us to get to know each others more and how we think.

  • http://match MB

    I’ve met a couple of men, who after 2 or 3 emails, have given me their numbers to call/text and take our conversations offline. I am hesitant since I am really new to this (and shy). Been three days now, I’ve not responded. Holding out hoping they don’t lose interest. But I feel like I need to send them a note because I am interested

  • gsl

    Interesting how all the online dating advice sites for men EXPRESSLY FORBID asking a girl out early so that she will not think of you as a creep!!! But no, a guy is too dumb to realize he likes you unless you ignore him?!! And here is the best part…..once you ignore him, he realizes its time to ask you out??!!! NOOOOOO. If a girl ignores me….I’m done. I feel nothing close to wanting to ask her out at that point.

  • Ian

    I looked at the contents of the emails and was wondering why the guy asked questions all the time but the woman did not really ask questions? I feel like the guy dominated all the questions? If I was the guy and the woman did not really ask questions to me, I thought she was not interested in me.

  • Jaya

    Great advice! Am getting fed up with the redundant “chat buddies” on these online dating sites…was debating whether or not to respond to a message but after reading this article I went back and counted and what do you know it was up to four emails so I am now not replying to this handsome man he can decide if he wants to go for a date and if not move on to the next one! It would be wonderful if you could write an article in regards to why men chicken out of meeting in person as well! Men will talk to me and ask for number and seem interested but then will not keep plans…. I’m only interested if I know we’ve got chemistry and I believe you need body language to gauge that!

  • Kieran

    I’m wondering the same thing as Ian. Based on the conversation, I don’t think that ignoring him would do the trick because she was ignoring him the whole time . . . by letting him ask all the questions while never posing any of her own. That demonstrates a lack of interest on her part – a lack of interest that would most likely drive me and Ian away.

  • Jess

    I don’t agree with this. I have gotten lots of dates after way more than 4 emails. I have also stopped responding after a few emails and guess what? The guys don’t write again.

  • Tammy

    I’ve been online dating on and off for about 2 years now. Just got back into it a few months ago. I get loads of dates, really I do. They ask for my number to get together generally around 4-5 exchanges. If they don’t, I just as this article says, don’t respond anymore, most don’t send another message and so what, they were not asking you out on a date anyways for whatever reason. The problem for me is not getting dates, it’s meeting a quality guy that is looking for what I am looking for and that is a relationship. That’s the problem I have.

  • Marie

    my question is: what to say, then, that will encourage a guy to ask for your number? What could “suzanne” have written in her third email that would have pushed Ed to ask for her number? Sometimes if you stop emailing a guy altogether, they think you aren’t interested and have met someone else – sometimes they just need that little push to let them know that you would love to meet up with them!
    Consider long-distance relationships as well. Maybe you can’t meet up all that easily, but still can find ways to talk on the phone or on Skype…

    It also depends on the guy as well – some are much shyer and scared of getting rejected to ask a girl out by the fourth email. While I am all for a guy pursuing me by that time, I’m not against giving him a few more emails to work up the courage to ask for my number.

  • Bamalam

    This article is kind of bogus and doesn’t account for a lot of factors in online dating. Ranging from a persons past online dating experiences to the barriers in communicating through emails. There’s a lot more to it than saying “four and done”. Not good advice.

  • Joanna

    This guy that I emailed first, have so far exchanged 3 emails each between us. I gave him my no. in my second email to him and he responded by giving me his in return. I have noticed that I have been the one asking the questions and sharing in kind. He shares based on what I’ve asked him but only ever asks one question to end each of his emails. I then went on to whatsapp, and he replies in kind then tells me to have a good day. It doesn’t sound like he’s interested and is only being obliging. I decided not to write or text him again because I am honestly tired of being the one who is showing most, if not, all of the interest. This article only solidified what I decided, thank you! Like Ian and Kieran, I feel my interest in him waning simply because I’ve been trying to connect and he’s showing little if no interest at all in me. Sad but I thought this guy was different from the weirdos I’ve met. At least I’ve responded by saying I wasn’t interested as they didn’t seem a good match to me. :( Sigh… this looking for love business is tiring.

  • Candice

    Wooooooooowwww! I’m totally guilty of this! Great article! I’m taking herd right now! No more emails!!

  • Candice


  • Daniel

    Weirdo’s, unfair, should do this, should do that, now, now ladies! You’re taking all the fun out of dating!! Getting to know you, getting to know me?? Have some jovial to and fro’ing messaging, agreed, don’t spend too long here, I offer my number up when we’re getting on or at the very least getting something stimulating back.. Move to texting, prior to this I probably suggested a meet up, have a bit more banter by text, fun, remember!! And then drop the date word, easy.. I should say, if you’re mailing a good looking guy expect to do most the work and accept if he’s out of your league, he’s seen your sort before lol He’s probably past demonstrative words of a caring nature and wants something that taps in to his primal nature. Good luck ladies x

  • Stirring Girl

    All interesting. I wonder though, why hadn’t Suzanne asked the guy one single question by message 5? Could her lack of interest (questions) give him the impression she simply had no interest? Perhaps if she was asking questions back, he would feel brave enough to ask, knowing there was SOME interest on her part, but by message exchange 5 He had asked quite a few questions and she hadn’t asked one.

    If the tables were turned and I was that man (I’m female), I would wait for some questions and then finally come to the conclusion that she was either not interested or rude. Suzanne really should have asked questions to show her interest. I’m not surprised he took his time.

  • smart

    The girl never asked a single question back to the guy. It would seem to me that she was unitnerested or didn’t have a great personality. I would have cut it off after my second email if she didn’t reciprocate a question. That is my biggest pet peeve when a woman doesn’t do that. Maybe the guy was very interested…he sure did hang im there long enough!

  • Krystal

    This is the best article yet! I will take heed, no more boring e-lationships without meeting. I am done wasting my time.

  • Krystal

    Agreed! I am doing the same thing.

  • Seriously?

    ok, no, this is stupid. okay? us guys are too dumb to take all these infuriatingly tiny hints. if someone stops emailing you, it’s because they’ve lost interest or simply drifted away. not ‘cos they wanna go out on a date. what the hell is wrong with girls making the first move??? i mean..
    “For whatever reason, they can’t get around to saying “Let’s meet” and following through with it.”
    Go on, you give it a try.

  • ksturges

    Hi Ladies and Gentleman,

    I am a casting director currently casting a new TV show about men and women dating then one just disappears. If this has happened to you and you live in the greater NYC area, please reach out to me at


  • Melissa

    I don’t really understand boys…so we girls are the complex ones :o? I actually tried not emailing the boy I liked for a while and yeah he became desperate and asked me for a date, at least for me it’s confirmed that they aren’t really brightest, it’s disappointing :(

  • CB

    To be honest the girl doesn’t sound like a good catch, he’s the one that constantly has to push the conversation along and ask questions and she doesn’t bother asking anything back, imagine trying to have a conversation with her in real life, boring!

  • Lala

    I disagree. It completely depends on people. I am a girl, young, smart and attractive, or so I am told, and I am perfectly okay exchanging two dozen emails before talking about meeting up. When random guys tell me they want to meet me after just 4 emails, especially ones as ridiculously short as mentioned in the article above, I usually blatantly refuse. I like to know that a guy wants to meet me because of my personality and not just for my looks. The latter is a complete turn-off for me.

  • Lala

    … Besides, like several men mentioned here in the comments, that girl was indeed completely boring to chat with!! Put in a little effort ladies, a little fun! The guys will thank you for it.


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