Why Are All My IM Conversations So Mind-Numbingly Dull?

I’m not sure exactly what my question is, but here’s the situation. Whenever I get to the instant messaging portion of online dating, 90 percent of the time I find the conversation to be completely dim. This isn’t even counting the guys who’ve never heard of proper grammar and spelling. The conversation is always filled with small talk – hello, how are you, what’s up, not much, just chillin’ – and nothing beyond it. The most conversation I get is “What do you want to talk about?” which I think just seems lazy, making the other person do the work. And “Sorry I’m not talking more” rather than just talking instead of apologizing but STILL not talking. I never get to know these people and just find myself annoyed at even having to fake interest in the “conversation”. So I guess my question is: what do I do? Do I suffer through the dullness and hope for a first date that might be better? Or do I write these people off as dimbulbs and move on to someone who has a little more to say? Or am I completely in the wrong for having this problem in the first place? I’m very interested in hearing your take on this.


Yet it stands to reason that the best writers/marketers are not necessarily the best people, and moreover, that among the vast majority of people with generic profiles, there are undoubtedly many gems.

Dear Patti,

You haven’t lived until you’ve IM’d with me. I’m telling you.

I’m quick-witted and flirty. I’m bolder than I am at a bar. I write as fast as I talk. I mean, literally, you would have to be insane not to fall head-over-heels for me after about a half-hour of IMing.

But that doesn’t mean that I’m a good boyfriend for you. I could be a player. I could be a liar. I could be wantonly flirting with you to pass the time post-divorce. All you know is that I’m funny and charming and articulate, and this is what passes for chemistry in this medium.

Now are you MORE likely to have real life sparks when there are IM sparks? Yes. Absolutely. But it’s not necessarily a predictor of much more. This same concept can be extended to profiles. We tingle in awe at a really good one and roll our eyes at the generic ones. Yet it stands to reason that the best writers/marketers are not necessarily the best people, and moreover, that among the vast majority of people with generic profiles, there are undoubtedly many gems.

How do I know this? Because they’re my clients. People like you — smart, successful, articulate writers, doctors, lawyers, professors, CEOs… with generic profiles that don’t give a hint of their personalities.

My guess is that these same people have equal trouble cobbling a conversation on IM. This is not a defense of them — just an observation that if 90% of people aren’t adept at profiles and IMing, it doesn’t mean that 90% of people are dullards and dimbulbs. There’s a good number who are just not skilled at these particular tasks. It may be second nature for the Undisputed Heavyweight Champion of Online Flirting (me), but for a great guy who is more comfortable working with his hands, he’s outside his comfort zone. (By the way, I hired a guy to put together my office furniture today. We all have our weaknesses.)

It’s easy to criticize guys with no game. But if most guys don’t have it, it doesn’t mean they’re dull.

However, Patti, your ability to capture the nonsense that most people spew in these so-called “conversations” also raises my hackles. (Yes, they’re raised! Look closer!)

As a prolific online dater who could literally conduct two IM sessions simultaneously without either woman knowing I was otherwise occupied, I struggled at my attempts to turn water into wine. And if you have an infinite number of dating options, sure, you can write off all of the boring people.

I just want to point out to you something that you might not have considered as a woman; how damn difficult it is to hit on you from scratch. Doubt it? Think that guys just need to “man up”? Fine.

Next time you’re out, go to a bar, find a really cute guy that you’d love to meet and approach him.

If you’re anything like 90% of guys out there, you’ll agonize for 30 minutes about what to say, and, when you actually get there, will freeze like a deer in headlights, only to come up with something like, “Hey, what are you drinking?”

It’s easy to criticize guys with no game. But if most guys don’t have it, it doesn’t mean they’re dull.

Join our conversation (27 Comments).
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  1. 1

    Hm, as someone who despises IM and always has (I think I can count on two hands the number of times I’ve ever IM’d, and half of those were for work, where our front office person uses it to check and see if we’re at our desk before sending an appointment back) I can’t really relate to this.

    However, I know that most people can’t type as quickly as me, so I’d imagine that at least half of these folks don’t feel like they can keep up (especially men, who have larger fingers that make it more difficult to use a keyboard).

    Personally, I’d have some stock questions ready to go: What are the five best books you’ve ever read and why? What’s your favorite international travel destination? How about domestic? How often do you cook from scratch at home, and what do you usually make? What kind of side projects do you do outside of your day job, either for fun or for extra cash?

    Anyone who can’t talk cogently about those things wouldn’t be a good match for me, because all of those questions are based on my own personal passions. Your questions might be different.

    I also tend to collect quotes (something I started doing when I met Jake, who has thousands of them compiled in a Word document) , have a blog reader with dozens of subscriptions on topics I’m interested in, and read news sites and listen to NPR, collecting links to stories. I think any of those things would work as a conversation starter.

    I’d be less concerned about someone who couldn’t start a good conversation, perhaps because they’re nervous, and more concerned about someone who couldn’t maintain a conversation, perhaps because we don’t have anything in common.

  2. 2

    I have had the same experiences as the woman who wrote the letter. Maybe this guy on the other end of the internet stratosphere is really great. But how am I suppose to know that, or even seperate it from the boring online converstion he is giving me? How am I suppose to be interested in guys that are just that lazy that they find typing “how r u”, “I like that 2″, will incite deep bone passion and interest in having to get to know them?

    How I solve this? I don’t talk through IM. I cut out this step because I find it bain and time wasting. I will learn alot more from a person through a phone conversation then I ever will through an IM session. When guys ask me for my IM screen name I just tell them ” you can have it but I really am not on there that much.” At this point either they will suggest talking on the phone, or I will. I don’t have to risk getting carple tunnel talking with someone that really isn’t a good match for me anyway.

    1. 2.1

      Yes, I don’t IM either. I gave up home internet last year, because I was spending too much time on that. Plus I’m using that money to invest in retirement funds. Win-win.


  3. 3

    Wanted to add that I will risk carple tunnel here dicussing what I do and don’t diagree with here on Evan’s blog. 🙂 Much to probably Evan’s dismay.

  4. 4

    @Honey 1, great suggestion to have prepared questions. Make sure they’re open-ended enough and intriguing enough that the person has to come up with an answer. A good one to ask men is the old chestnut, ‘Ginger or Mary Ann – and why?’ That will tell you a lot about him and his intentions on the site without coming out and asking him directly about what he’s looking for. (Note that the above question might draw a blank in men under age 35.)

  5. 5

    Hi Mark! I think I’m pretty good at the online flirting, too, except for the fastness. I prefer emails back and forth so that I can have time to choose my words and phrases carefully, but I’m slowly graduating to IM’s. Like everything else it takes practice. Lots of open-ended questions. After reading one guy’s profile I messaged him with “Wow, you’re tall! What do you do in Nebraska?” He IM’d right back and we’re still in touch. Simple, but effective.

  6. 6

    I stopped IM-ing several years ago. Too many times that is all the men wanted to do. Chat. Now I send 2 or 3 emails then it’s phone time. Most men seem okay with it. The guyI met 2 weeks ago was ready for the phone conversations after the first email, I was fine with it — we had a lot in common. Just not enough chemistry when we met.

  7. 7

    I only IM when I’m on-line at the dating site I currently use. While I MIGHT not be as good as Evan at multiple, speedy, and lively IM-ing, I’d say I can hold my own. But it all depends on whether the person messaging me is responsive. My experience has been that younger men are more likely to IM, while men my age or older are more likely to email. That’s just a result of the techno-gap between those who grew up with keyboarding, cell phones, and texting, and those who, like me, need to first remember where they PUT their cell phone in order to answer it, and then need reading glasses to see who’s calling. The younger man’s opening line is typically: ” ‘Sup?” while the the more mature male messenger will start off with something like, “Hi! How are you this evening?” Or they’ll make a comment about something I’ve written in my profile. I consider IM’s the most risk-free form of communicating there is. If you IM someone and they don’t respond, there are a host of reasons you can tell yourself to soften the blow of rejection….maybe the guy is chatting with someone else at the moment, or taking one of the site’s tests or surveys,or in the middle of a heartfelt email, or…he’s simply nodded off. When you initiate an IM, you’ve briefly inserted yourself, uninvited, onto someone’s screen-space, so you’d better have something to say…or why bother? I’ll banter with just about anyone if they’re lively and engaging, but if it starts to get laborious, stuck in quagmire of “How is Your Day Going?” followed by (dread) weather chatter, I’ll just stop responding & generally the other person gets the hint and that’s that. Plus, you usually have the option of being visible/accessible to others for IM while you’re on line, or not. I’ve had some very enjoyable IM exchanges, as well as those that fizzled quickly. I agree that there are probably men out there who really are “gems” in terms of being a good man for the long haul, but who are awkward or lackluster in their initial approach. But — hate to break it to you, Evan — every guy I’ve ever heard from who was stilted or unimaginative in an email, IM, or phone call, turned out to be even less stimulating or engaging in person. Except in person, he was sitting right across from me and there was no little “x” in the upper right hand corner I could click on to just…uh, make him go away. I know, I know, I’m a cruel b**ch, but life’s short & if a guy is going to pop up onto my screen, he’s gonna have to come equipped with something to say. Besides, for every shy, initially awkward guy, there’s an equally shy and awkward woman out there who will find him just PERfect, as is, no clever lines required. Dontcha think?

  8. 8

    Why IS there an “IM portion of online dating” anyway? Sending one or two e-mails then moving to an actual real-time conversation mode like the phone seems obvious for a process where the goal is to see and touch. (At least, I hope that’s the goal.)
    I’ve IM’ed with exactly one person I’ve dated, and halfway through the session got sick and tired of having to occupy myself with something else while I waited for responses, and I picked up the phone. To me it’s both impersonal and a time-waster.
    Now, I can see making initial contact through a chat feature (and good on those women who use it), but after the first hellos, the clock starts ticking to making actual undistracted personal contact.

  9. 9

    @ BeenThruThe Wars – yeah, just like “Betty or Veronica?” would, despite the fact that the issue was only settled recently and, since he chose Veronica, made more than a few waves 🙂

    A more contemporary alternative would be: Carrie, Samantha, Miranda, or Charlotte? If you’re asking a woman, try: Big or Aiden?

    1. 9.1

      Obv. Aiden. Who was way too good for Carrie anyway.

  10. 10

    I think that guys who insist on IM’ing at first aren’t serious about wanting a ltr. Even if they’re too shy, unless you know the person already, I think it’s an impersonal way of getting to know someone. Similar to texting, it doesn’t replace an actual conversation.

    I like JerseyGirl #2’s idea, suggesting another form of communication.

  11. 11

    I’m another one who completely cuts out the IM. Like Evan said, I’ve found that how a person “talks” in IM doesn’t necessarily reflect their true selves for good or bad. Also, as someone else mentioned, many times guys want to flirt via IM, but they’re not interested in going any further. I want a REAL relationship in the REAL world, not an IM flirt buddy, so what’s the point.

    My advice would be that in future when a guy wants to switch to IM, tell him you don’t have it. The guys that aren’t willing to take the next step and meet in person (or take the time to get to know you by email and THEN meet in person) will drop away.

    If you do want to continue to IM guys, I would suggest getting “1000 Questions for Couples”. Obviously a lot of the questions won’t apply or be appropriate to ask someone you haven’t even met in person yet, but some of them are quite fun and the answers will be enlightening.

    Even a person who’s not great at communication in IM should be able to answer simple questions like “What was the last movie you saw at the cinema?” or “What’s your favorite holiday and how do you celebrate?” The answer should be a spring board for other comments and questions.

    They key is to ask SPECIFIC questions that prompt an answer. Think about it. If someone asked you, “How was your day?”, that’s pretty generic. It’s so general that unless something really unique happened, you’re answer would probably be something like “Fine”. However, if someone asks, “What was the last song you got stuck in your head?”, you could probably come up with something. I know I could… “Sex on Fire” by Kings of Leon. That could lead into an interesting discussion of just how such a song got stuck in your head and whether or not you like the King’s of Leon.

    If you still get monosyllabic answers and zero feedback after asking SPECIFIC questions, it’s time to rethink. And before you blame it all on the guys, maybe you should take a look inside. Remember, when you point your finger at someone else, three fingers are pointing right back at you. Maybe you’re not as good at IM communication as you think you are…

  12. 12

    FrogPrincess, I agree in theory that asking different questions is good or replying differently. But to me, when someone asks me random questions like that, while I appreciate the effort, it comes off sometimes as forced. I want the conversation to go more naturally. When men ask me what I do for a living, I don’t tell them that I work for the newspaper industry. I will say something completely ridiculous like “Oh I tame lions”, ” I take in injured Flamigos and rehiblilate them into the wild”. Which either has them getting into the joke or looking at me like I infact do tame lions or have a flock of flamigos in my back yard. But that quarkiness fits into my own personality so I don’t know if it would work for everyone. And then after the joking, I do tell them what I do and we are both more engaged in the conversation.

  13. 13

    As usual Evan has made some great points. Like others, I don’t care for IM. Ican’t type worth a darn and I refuse to use text speak. The inner grammarian cringes and becomes ill if I force it.

    I actually have developed a list of questions to use in emails as those too, can become tedious. I do use the Ginger or Mary Ann question but not the Sex in the City as I’ve never seen it. I’ve used Daphne or Velma. Others include favorites and why, sunrise vs sunset, chocolate, vanilla, or strawberry, etc. Some are silly and some are a little more serious, such as If you could pick 4 people to have dinner with who would you choose & why.

  14. 14

    I agree that the ‘Ginger or MaryAnn’ or ‘Which character from SATC” will vary depending on your age group, but i like the idea of that question; it’s cute.

    I think anything where you are askign about someone’s hobbies or interests works, as well as more general questions like, where’d you go to school? (if the people you are targeting went to college) What was your favroite thing about your college town, etc.

    I think some of the ‘deeper’ questions like ‘what 3 people living or dead would you want to sit next to on a plane’ are a little forced for my tastes and too deep for IM (maybe even for email too). I prefer to keep things lighter and reveal things about my personality in more humorous, light-hearted ways, especially at the beginning. I’d have to think so long about how to answer the ‘deep’ questions, it’d delay me sending out the email which goes against what we’d be trying to do!

    And you don’t have to succumb to text speak when writing IM’s. They’ll just be a little longer 🙂

  15. 15

    Here’s an Oddball reason not to IM: I was in a car accident and it damaged my writing ability. Given time, I can write a bright and sparkling email. My verbal skills are fine so on the phone and in person, I can carry on a satisfying conversation with the bright, dynamic women I prefer.

    By not IMing I avoid a venue where I would not succeed. Because it avoids wasting a dating opportunty, I believe it is a service to both of us.

    I am honest about my mental deficit, though I usually wait a few days to bring it up. Of course, I don’t “click” with everyone, I have dated a number of interesting women and am currently in a year-long relationship with a corporate trainer.(engish major, corporate communications)

    Don’t have too high expectations for IM. My current success is based on avoiding it.

  16. 16

    I learned long ago that IM is a waste of time. It’s time-consuming and gives no accurate sense of someone’s personality or intelligence. I once had great IM chats (good phone calls too) with a guy and when we met in person, there were no reall sparks. I just don’t think IM gives much of a sense of a person. With email, you can at least get a sense of whether a man can construct a coherent sentence. Telephone gives a sense of personality and connection. But of course, nothing beats meeting in person. You’re not going to click with most of the people you meet anyway, so why waste time with IM?

  17. 17

    I cut off those who can’t IM

    and I don’t talk on the phone with men I don’t know better through IM.
    Phone is just bore bore bore and bore, unless one knows the other person a bit better.

    So in short.. if a guy doesn’t talk have good IM skills, he is not interesting to me, nor going to get my phone number since I am just going to feel ill-at-ease when talking on the phone to someone who wants to asks things about me, and I don’t have any interest in him (= no interest to tell him anything about myself, since I don’t want to meet him either)
    Again.. I think online fluency does often correlate the presence that one has IRL (not always but often). If a guy can’t hold his own, I’m not going to have any sexual chemistry.. and therefore there is no point in meeting him.
    I have tried.. met over those 400+ guys over last 12 years.. so I know myself, and no matter what Evan says, I am not going to settle to have a relationship without having good sexual chemistry and lots of good sex to go with it.

    So a guy needs to have looks that I like and a plastic brain= he needs interested in several subjects, even new subjects that come along outside his normal parameters, proactive, and fluent with words. Those qualities need to be combined to emotional stability.. and I start to feel chemistry.. that is essential to a relationship, or it is a no go.
    If that is too much, I prefer to be single. =)

  18. 18

    I’ve done a s*hitload of flirting over IM and I’m pretty good at it. It’s got it’s place, just like any other form of electronic or online communication. What’s great about IM is I find it easy to be suggestive and sexual over IM without it seeming creepy…it comes across flirty. Anyway, if you’re unskilled at IM, I would just use it as a way to touch base and set up face-to-face dates. That’s how you really find out if someone is interesting or not.

  19. 19

    Who says that most people are good at face-to-face conversation? Maybe it’s more interesting because of visual, vocal, and chemical factors. IM lacks those, so….

  20. 20

    I feel like meeting someone the old fashioned way will give you more success. I might be very wrong though! But I feel for me, meeting someone face to face and going on dates right away is a better option. I don’t think I would like IMing someone and emailing for weeks before I actually meet them. What if I spent all that time having a connection through the computer but then there was nothing there in person. It just sounds like a waste of time to me.

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