Why Your Online Personality Should Be Better Than Your Real Life One

a young couple looking at each other while smiling

You go to a party.

You see someone attractive.

You make a smooth approach over by the punch bowl.

You smile. You get a smile back.

It’s time for your most winning line.

“You look very attractive. I’ll bet we have a lot in common. Tell me about where you grew up, how recently you got divorced, and whether you have any baggage I should know about before we embark on our relationship.”

Wait, that’s not your most charming opening line?

It is when you’re dating online!

Go into your inbox. Check your communication. Does it sound a little serious? Is there any personality in there? Are you asking earnest and probing questions?

If so, you forgot the fundamental rule of flirting: it’s supposed to be FUN!

And that’s the thing we often forget when we’re meeting people in cyberspace: Online flirting and offline flirting are the SAME exact thing.

It’s only when you act like they’re different that you run into problems.

Online flirting and offline flirting are the SAME exact thing.

You know what flirting is. You know how it makes you feel alive. How witty banter can strike a provocative chord, even if you weren’t talking about sex.

Flirting is verbal foreplay. Yet most of us forget the foreplay part.

We go right for the close – to secure a date and gather important information – and then wonder why no one wants to continue talking to us.

Men write: “You’re hot. What’s your number?”

Women write: “I’ve found that lots of people lie on here. Are you telling the truth about your age and your photos?”

Men write: “Meet me at Starbucks on Tuesday at 3pm. By the way, my name is Evan.”

Women write: “Your profile doesn’t say anything. Tell me more about yourself.”

Ugh. No wonder online dating seems like such a chore. We turn communication into a job interview and then wonder why it all seems so stilted.

I’d like you to approach online dating flirtation in an entirely new way:

Online flirting should mean striking the same exact tones as real-life flirting.

And if you’re saying to yourself, “You’re wrong, Evan. It’s much more difficult over the computer,” I’m going to have to disagree. It couldn’t be easier.

In Finding the One Online, I hold your hand through the entire online dating process, from choosing a website, to writing a profile, to getting you photos, to writing witty and winning first emails.

Imagine I’m standing next to you at the bank. That limits my conversational options. All I know is that I’d better come up with something witty to say:

  • “Are you making a deposit or are you here to rob the place?”
  • “These lines are always so long. Doesn’t anybody have a day job in this town?”
  • “I don’t know why I cash these $2.46 checks, but if the phone company sends them to me, I guess I have no choice.”

In all of them, I’m being silly. In all of them, I’m not asking you for a date. In all of them, I’m not pushing for deep information. I’m just making light conversation over NOTHING. That’s flirting. Real conversation comes later.

Successful online flirtation is about being the most fun out of any other woman he’s emailing.

To be a good flirt, it helps to be fast on your feet, but most people can get by just fine. Flirting means exercising your personality in real time, not putting any pressure on the person for a date, and believing that the person will be receptive to conversation.

Now let’s take this to the online realm with two questions.

Q: Where do you have more information about someone – the bank or Match.com?

A: Match.com

Q: Where do you have more time to construct a witty response – the bank or Match.com?

A: Match.com

The defense rests, your honor.

When you’re sifting through people’s profiles and have all the time in the world to come up with something to say, there’s really no excuse for not keeping things light.

Because keeping things light is what allows us to let down our guard and connect.

It’s not about trying to carefully prod to find out if he’s a player or whether he’s hung up on his girlfriend. Successful online flirtation is about being the most fun out of any other woman he’s emailing.

I dated online for 10 years and if I did one thing right, it was knowing how to flirt. When other guys were pushing too hard for a phone number or a date (you know who I’m talking about!), I’d keep making women laugh. By the time I finally did ask for her number (after a week or so), she was excited to give it to me. And why not? She’s finally going to get to meet the witty guy who wasn’t trying to steamroll her into the bedroom. What a novel idea!

A lot of people – maybe even you – may feel that your personality is dependent on where you are. You may say, “I’m not good on email,” or “I’m terrible on the phone,” or, “I’m a lot better when I’m comfortable with someone”.

Well guess what? You’re never going to get the chance to get comfortable with anyone until you realize that your personality has to shine EVERYWHERE.

And if you can be warm and playful with someone you know, you can be that way with someone you don’t know.

And if you can be warm and playful with someone you know, you can be that way with someone you don’t know.

And if you can be funny with a stranger at the bank without having any information, you can be funny with a stranger online when you do have information.

You are the same woman whether you’re emailing, talking on the phone, or meeting in person. You have the same stories, the same beliefs, and the same vocabulary.

All that’s different is how you choose to handle it.

I fully explain my two email techniques – Opinion Openers and Fun Fiction – in Volume 4 of my Finding the One Online program. Once you learn how to do this, it’s like magic.

Men will be eating out of the palm of your hand, because you’re the only woman who knows how to flirt with him the way HE likes.

So get over that idea that you can’t flirt online and start making some cocktail party conversation with a stranger.

Join our conversation (19 Comments).
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  1. 1

    Evan wrote: A lot of people — maybe even you — may feel that your personality is dependent on where you are. You may say, “I’m not good on email,” or “I’m terrible on the phone,” or, “I’m a lot better when I’m comfortable with someone”.
    Well guess what? You’re never going to get the chance to get comfortable with anyone until you realize that your personality has to shine EVERYWHERE.
    And if you can be warm and playful with someone you know, you can be that way with someone you don’t know.
    That’s actually the take home quote for me, and this is from someone who’s not interested in finding a date.   I’m definitely different with people once I get to know them, and this is something that I’d like to work on.   As someone who moved around a lot growing up, you’d think I’d have a more open personality to make friends more easily.   But I was always making friends just as it was time to leave.   And this has carried over into my adult life.   It takes me awhile before I start acting like my “truest” self, and even longer before I consider someone as a friend (rather than a friendly acquaintance…of which I have many).   Anyway, food for thought!

  2. 2

    A-L, me too. 🙂 I am not a natural flirt in real-time or online. I need to feel more comfortable around a person before they can get to know the flirty and zany parts of me. In my younger days, especially, I was terrible about even noticing when a guy was checking me out. People would often comment and ask me if I noticed the guy staring at me. I laughed reading Evan’s bank flirting lines because I’d likely not recognize them as flirts, except for maybe the first one.
    But I do know how to write using different styles, if I so choose, like teasing banter, and I never grill anyone for information because that’s putting the buggy before the horse; it’s way too soon.

  3. 3

    Ditto,   I was the tomboy growing up, every guy’s buddy or sister.   Flirting has not necessarily come naturally to me.   It took a huge wake-up call several years ago combined with timely advertising from either eHaromony or Match.com to wake me up that if I wanted something different I needed to do something about it, not sit and wait for it to happen to me.   I had a lot of first dates with men, rarely did I have a follow up.   Thanks to Evan’s sound advice, I know why now & by in large it had to do with the way I presented myself.   I’ve had more second and third dates and even one relationship in the intervening years because of what I’ve learned. I will say it’s easier for me when the man starts it.

  4. 4

    I purchased Finding the One Online, and although I found it to be pretty insightful, the Opinion Openers and Fun Fiction techniques just do not work for me. When I have initiated contact with men using these techniques, the response is…crickets. It’s only when I’m already engaged in an email conversation that men seem to be receptive to me acting silly or playful/flirtatious. I must be doing something wrong!

  5. 5

    I met Jake on MySpace (no friends in common).   I liked his profile, and under “who I’d like to meet” he put something along the lines of “Fun, friendly, intelligent people – who doesn’t?”

    My first email to him had a subject line “Have You Met Them Yet?” and the email said “…the fun, friendly, intelligent ones?”   We exchanged 3 or 4 short emails and then he tried to add me as a friend and couldn’t because he didn’t know my last name.   He sent me this dorky email that said, “Will you be my friend?” and I said, “That depends, I go out for beer with my friends!”   He asked me out and we hadn’t even exchanged phone numbers yet 🙂

  6. 6

    I really think I forget to flirt myself and maybe never felt comfortable doing it.   I definitely need to work on it.   It doesn’t help that I’ve been using the free sites. I’m convinced most people on those sites are not serious about wanting to find someone for anything other than a quickie.   Nothing wrong with that, but maybe I should try something like Match.
    I’ll have to keep thinking about it, but I could definitely use more flirting.

  7. 7

    I have flirted like mad online and am very good at it. The men I met flirted like mad too. I met the ones who were the best at flirting and found out they were VERY different online than in person. The problem was they were great flirts online but miserable flirts in person. Its funny how personality can be so different from online to real time. That same funny, fun guy online always turned out to be a real dud in person.

  8. 8

    @ sjz # 7 I wonder if it has to do with how confident one is with oneself.   There is a sense of anonymity or maybe safety’s a better word for it, that one can hide behind when online.   I think of Brad Paisely’s song that has, among others Jason Alexander in the main role.   Hilarious.
    @ BlogDaddy # 6   I’m a member on a two different free sites.   I have, in the past been a member of Match, Chemistry, and eHarmony.   Without a doubt my worst experience has been on Chemistry, a paid site, but for me in essence is free.   I joined when it first came out and the deal was back then your membership was free until after the third date.   That third date never materialized for me and somehow, I don’t recall how it morphed into a life time membership.   I’ve had a number of different dates with men who I met through Match as well as eHarmony.   I’ve only had one date from one of the free sites, but I haven’t been all that active in searching for matches.   When I was last on Match you had to contact so many different members a week -(email not wink, I think) in order to qualify for the free six months if you hadn’t found someone in the first six months.   I think you have to put forth some effort into any dating site, free or not.   I will say I’ve received more emails of the, “Your attractive are you interested in me?” or, even better, “What’s up?” variety on the free sites than I did the paid.

  9. 9

    To sjz #7, your experience is one that is all too common on the Internet. A lot of people take on a different personality online, whether at dating sites, forums, game playing, etc.
    I think flirting in real-time is difficult for most men and women, unless they’ve had a glass or two of wine. 😉 It takes confidence, but not too much. Otherwise, it’s arrogance. It takes wit, timing, quick thinking, humor, and the ability to accurately read and interpret people’s facial cues, tones, and body language. Otherwise, you just might look like an idiot. 😉 Oh, and a little mind reading doesn’t hurt either.

  10. 10
    Evan Marc Katz

    I think, like any skill, some people are natural flirts. I’ve been flirting since I was a little boy, or so I’m told by my Mom, and it’s certainly made things easier. That said, if you follow directions, you can get better at it. Flirting assumes one thing: that whatever you say MATTERS. It assumes that the other person WANTS you. It assumes that it’s YOUR choice whether things go to a romantic level. In short, flirts have power over opposite-sex situations because they FEEL they have power over opposite-sex situations. Which is why flirtatiousness and confidence often go hand in hand. Watch your guy friends or girl friends who are good flirts. What do they have in common? It’s not looks; it’s the belief that people fundamentally like them and are attracted to them. Once you believe that, everything else comes organically. If you don’t believe that, it’s really hard to fake it.

  11. 11

    Evan, agreed. I have watched other women flirt and noticed that sometimes it’s over the top or borderline desperate. I doubt most men think so. 😉
    Even though flirting doesn’t come natural to me at first, I haven’t found flirting to be necessary, though you don’t want to sound too serious in online dating. I can feel and see other people’s attraction to me, and being open with a smile and conversation works well.

  12. 12
    Karl R

    Diana, (#11)
    An open smile and conversation count as flirting. I’d consider them steps 1 & 2.

  13. 13

    Karl R, #12-

    Isn’t that the same as friendliness? An open smile and conversation is how I would also talk to same-sex people I’d want to befriend.

    As for flirtation- I don’t know if I’m good at it or not. I certainly wasn’t when I was younger. What’s irritating though- is that when you do initiate friendly conversation with men, almost 90% of the time, they seem to think you’re hitting on them. I’ve had so many instances where a man will suddenly stammer- uh-uh, I have a girlfriend, that I rarely try to make conversation with men first anymore, whether I’m interested or not.

  14. 14

    Karl, I think of flirting more as being coy and playful, teasing banter, and a little amorous without serious intent. When I go to a singles event, I enjoy getting to know people, and that begins with being receptive, smiling and engaging them in conversation. I guess I see this more as being friendly and sociable. Now if I were to wink at the guy in a sort of teasing, laughing way, or lightly touched him on the forearm, or flipped or touched my hair a bit, tilted my head a certain way, that kind of thing, then I’d feel like I was flirting with him.

  15. 15
    Karl R

    Sayanta asked: (#13)
    “Isn’t that the same as friendliness?”

    Of course. Unfriendly people don’t get many dates.

    Sayanta said: (#13)
    “I’ve had so many instances where a man will suddenly stammer- uh-uh, I have a girlfriend,”

    I’d say that proves my point.

    But I must hang with a more suave crowd. We’ll just casually refer to our girlfriend/boyfriend without making a big deal about it. Then the conversation/flirting continues with everyone understanding the boundaries.

    Diana said: (#14)
    “I think of flirting more as being coy and playful, teasing banter, and a little amorous without serious intent.”

    That’s usually where it progresses. But it’s easier to engage in teasing banter if you’re already conversing with the person. And if it’s a purely social conversation, it’s rare for me to carry on a conversation without tossing teasing banter in.

    If you were to walk up to a guy, touch his forearm, flip your hair and wink at him, he’d probably think you were coming on very strong. If you were to do one of those actions after chatting for  15 minutes, it would seem like a much more normal pace for flirting.

    A person can flirt with or without intent, and it will probably look very similar to an outside observer. But if my intent is to get a date with the woman, all I need to do is get far enough to get a phone number. And I don’t need to go beyond friendly conversation and a little witty banter to get that.

  16. 16

    I agree with Evan….being a natural flirt is something someone is born with.   Those not born with it, it  feels like work! Sometimes just downright painful and excrutiating.   I was shy when I was young so, that time was lost for practicing my flirting skills.   As I got older, wiser, stronger, and more of a “what-e-ver” attitude it got alot easier.   Confidence was something that was always there and dormant, then it came out with a loud BANG! I am not a real big flirt…regardless of what I said just now…I just don’t choose to be overly flirtatious in person or online.   Flirting is a true art.   Too me I can stand in a room and just watch the amount of it flying around.   Mostly like 98% of it looks so over the top!  
    That is why,   I so agree with Karl R….guy.. you hit it right. Teasing banter is where it’s at for me.   This kind, no matter what is so much less contrived and obvious.   It is a great way to feel out   who the person is.   Sometimes I can tell just by that interaction that, yikes no need to go further or wow here we go!   Even still if it’s a – I don’t think so, it’s been a fun conversation and maybe made a friend.  People can walk away – okay. No ones  hopes are damaged. Ego’s left in tact (no matter what size).   
    Just a bit on how I see it….how it works.. for me!

  17. 17

    Flirting is also a good way to qualify someone and get a handle on their personality. If I’m exchanging several rounds of witty banter and cleverness, I know the other person has a sense of humor and I know what type of humor they’re into (sarcastic, goofy, dry, etc), which tells you something about their personality.
    One gripe I have is that the most chicks are terrible at verbal flirting but great at physical flirting, while guys are vice versa. It’s been my experience that the gals are either scared to flirt verbally (don’t want to encourage him) or just plain inexperienced, and it takes a really skilled dude to illicit her true wit.

  18. 18

    This is a very interesting and amusing post! I agree that sometimes online dating seems to be like a chore. Please don’t ask questions as if you are interviewing a job applicant. Be spontaneous and cheerful.

  19. 19

    I have recently bought the Finding the One Online program, and have been employing the techniques suggested. Though it is early days is using the techniques, I think there are cultural differences between dating in the US vs the UK. I remember reading an article about Gwyneth Paltrow relocating to the UK and she said the very same thing. In the US, flirting and dating is a very normal game played between people. In the UK, the same fun games are just not played (at least not in the same way – not with witty banter). So here I am trying to write these flirtatious emails to differentiate myself, and responses are usually fairly monosyllabic, or go directly to “where do you live?” (because travelling across London is such a chore, no one seems to want to make the effort.) I will continue to employ Evan’s techniques, but it’s an interesting observation of potential cultural differences in the dating game.

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