OK Cupid Pro Tips aka How Not To Waste Your Time on OKCupid

Name: PrestonChainsaw
Comment: First and foremost, your website is a God send. I found it while googling an issue I have and find that it hits all the right notes from beginning to end.

So long story semi-short, I messaged a girl on OKC whose profile I liked and also found to be very beautiful. I started with a corny joke, then self depreciating comment, told her why I like her  her profile, and then I wrapped it up with a question.

She responded within a day, which is rare and very nice. She went along with my joke, answered my question, and went on to engage me as well. Now this went back and fourth with about 14 messages, 7 from me and 7 from her, all within 6 days.

We responded well to each other, asked and answered different questions, made jokes, and very much engaged each other with great rapport. Now I can’t be sure but at one point it looked like she was signing on just to respond to me… And I’m sure she gets a lot of messages in general.

Then pretty much things fizzled out with no warning. It took her 4 days to respond to my last message, which is fine of course, people get busy for a lot of different reasons. I then responded to that one and since late August that was it.

3 days later I found a typo in that last message and followed it up with a funny correction, and still nothing. Now I should also mention that my friend had recommended I finally ask her out for coffee or lunch, as it was going long, even though it wasn’t even two weeks. But he was right in that we did have enough info on each other and seemed comfortable talking and that it wouldn’t be out of sorts to ask.

So when she didn’t respond to the lunch request and the short correction, I sent a short follow up a full week later. I mentioned something we talked about earlier, and then went onto explain that I didn’t mean to seem like I was rushing things and that if she’d like to keep talking or text that that would be fine. That was over two weeks ago and still nothing.

Now I know this seems like a long story where the answer might simply be that she flaked out, but I’m curious as to your thoughts anyway. And it wasn’t even the message where I asked her to lunch that broke our stride but the one before it.

Anyway, I’m sure there could be a million other reasons. But I’m surprised and obviously disappointed that she didn’t even respond to say why she lost interest. I get that that’s awkward to tell someone, especially someone you were really clicking with, but it’s also just as awkward to stop cold. So your thoughts and or critiques are greatly appreciated.
Age: 31
City: Philadelphia
State: PA

This woman didn’t lose interest. She was never interested in the first place. She was being polite and nice by responding to your original email and answering your question. I say this because, as I have always maintained, anybody who is willing to drag out their conversations for several days with someone online either isn’t all that interested, pre-occupied with other options, ambivalent or never had any plans to meet anyone from the site to begin with.Another disappointment in my Match experience was that the guys I communicated with would send one message a day, and in that message would be a banal question like, “So why is Fall your favorite season?” Nope. Want to get to know me? Let’s meet. In cases like this, I sense that the guy isn’t assertive enough to ask me out. Which, for me, is an issue since, you know, I’m not exactly submissive. That’s my experience, though. YMMV.

It sounds like this woman was just engaging in polite conversation and eventually got tired of replying to you.

This scenario exemplifies why I suggest to male and female clients NOT to ask questions in their introductory email. My advice to them is to make their initial message brief and succinct and include a very clear directive. Messages should follow this template:

  • Open with a brief salutation.
  • Tell them that you liked their profile.
  • Include a line that refers to something specific in their profile.
  • Invite them to take a look at your profile.
  • Close by telling them to reply back if they’d like to chat potentially meet up at some point. That’s a clear directive.

Messages should not include:

  • Comments about the person’s looks or body.
  • Self-depreciating humor.
  • Short bios.
  • Questions.

I would guess that a large majority of empty e-lationships that people develop with folks they met online are borne of innocuous questions in the original email. They go back and forth for days writing brief and without substance notes and a date is never set. If you and this woman exchanged 14 messages and there was never one mention about meeting, it was because she was not interested. If she were, she would have taken you up on your suggestion to meet or hinted that she wished to take things offline. It sounds to me like she was doing what many people do and passing her time on the internet by answering polite questions.

A few other tips:

  • Be assertive. Dilly dallying for a week swapping messages is a time suck and not all that fun.
  • Cut your losses quickly. Getting invested in a one dimensional persona on a dating site is not a productive use of your time.
  • If someone doesn’t respond to a message, they’re probably not interested or have moved on. It’s fine to follow up once a few days later if the conversation dropped off. But that’s it. More than that and you look desperate.
  • If you are going to follow up, don’t use some frivolous excuse like a typo. In most cases, people know the word we intended to use.
  • Nobody is going to tell you why they lost interest. Nobody. That’s an unreasonable expectation. And even when we do get responses to such queries, rarely do we get the whole truth.
  • If you like someone, ask them out and respond in a timely fashion. This goes for men and women equally. One message per day, to me, doesn’t indicate interest. Especially if plans haven’t been made after the third email or so.
  • If you have to constantly be trying to engage them or schedule a date, take that as a hint and fade.
  • Screw The Rules of who should ask whom out, etc. However, you can not go wrong if you accept and abide by basic social expectations and guidelines. If you’re having an ongoing conversation with someone via email, a 4 day drop off from the other person is just impolite.

How we interact with people we date or want to date really isn’t any different than how we interact with other people in our lives. For some reason, many people think that there’s a whole secondary set of rules for dating that are actually counter-intuitive to healthy interpersonal interaction.


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26 Responses to “OK Cupid Pro Tips aka How Not To Waste Your Time on OKCupid”

  1. Becca Says:

    You should never be this invested in a person you have not met. There have been times when I have legitimate thought I responded to someone’s message and didn’t, so a follow up doesn’t bother me. But 3 or 4 additional messages is just creepy. Like Moxie said its very possible she wasn’t interested the whole time, but if she was but for whatever reason she didn’t respond, there is no way she will now.

    And what is the 2 week time table for waiting to meet someone? I’ve never heard that. My first thought when reading it is you annoyed her because you weren’t asking her out and she bailed. By the time you did she was freaked out.

    • James Says:

      Maybe I’m doing it wrong, but I keep my messages to a minimum with a minimum of chatter. If I get a response I try to get a number right away. If I get a number I call within a day or so. And I ask the woman out. It usually works but you will get the wishy washy and neurotic ones from time to time. By doing it this way I weed out the time wasters and those who have no interest.
      Never invest any time or emotion with someone you have never met. Until such a time they are just another image on a screen.

      • Helen Says:

        I would agree to meet right away but a man has to give me a reason to want to meet him. If we exchange 2 or 3 emails about the weather, then you want to meet, I’m going to be hesitant because I don’t feel like I know much about you.

  2. noquay Says:

    I agree; asking to meet should be email #1. Even if the person is interested, not wanting to meet right away is a red flag. I corresponded with someone from fairly far away for a month or so, I finally made the move to meet and found he was a good 30 lbs heavier than his photos indicated. There’s a reason why they do not want to meet.

    • Helen Says:

      Not necessarily. You don’t know who you’re talking to. It’s best to just feel them out for awhile but don’t invest too much in them in case they turn out to have misrepresented themselves or lied.

  3. The D-man Says:

    Dude, 14 messages? I usually ask a girl out in the very first one, and definitely by #2.

    I bet she got sick of waiting for you to ask and so assumed you were spineless or had something to hide. Don’t waste time trying to build rapport online. If anything, you want to be mysterious. Build rapport in person.

  4. Yvonne Says:

    Personally, I like to exchange a couple of emails, then talk on the phone (a good way to weed some people out), and if that goes well, set up a meeting. But 7 message exchanges is pushing it a bit. I would not agree to meet someone without talking to them first, but that’s my comfort level. Continuing to send messages to someone after they haven’t responded to one or two emails is just excessive.

    That said, I think this girl was just killing time. She may have had mild interest, but probably someone else showed up who interested her more. It’s really that simple.

    • Speed Says:

      When a woman says, “I need to talk on the phone, before meeting,” it means she is nervous, ambivalent, or flaky about the whole online dating process. It also means she wants to get her guys jumping through hoops before they’ve even met.

      2-3 email exchanges, and either the woman’s up to meet for happy hour at a local pub or she’s not. If a woman wants to delay, phone chat, whatever, I’m out.

      • Yvonne Says:

        I’m not nervous, ambivalent, or flaky about the online dating process. However, I value my limited free time, and don’t want to waste it meeting someone that I can’t even have a decent conversation with. It doesn’t happen often, but I’ve encountered men who seemed okay in print, but were weird or obnoxious on the phone. And as I said, that’s MY comfort level. A man who doesn’t respect that would not be right for me. YMMV.

        • WO7 Says:

          Chemistry on the phone does not correlate into chemistry in real life. You’re really not learning anything about how you get along with someone from a phone conversation; and more likely, you’re just wasting the easy conversation starters that you should be using for your first in person meeting.

          I’m busy too, and I certainly don’t have any time for phone conversations. My only available time is during the day (when people are working), or late at night (when it’s rude to call).

          • D. Says:

            It’s true that just because you click on the phone doesn’t mean you’re gonna click in person.

            But if you’re seriously turned off by someone’s phone presence, chances are they won’t dramatically improve if you meet them in person.

            Fran Drescher still sounds like Fran Drescher whether she’s on the phone or on the other side of the table from you.

            And really, if you’re worried about a 20 min phone conversation, which will include setting up the date itself, killing all your conversation topics…maybe you and the other person weren’t gonna hit it off no matter what.

          • Yvonne Says:

            I get that phone chemistry doesn’t always translate into real-life chemistry. But that isn’t the point. A bad phone conversation is a pretty good indicator that the real-life chemistry won’t be good either. I’d rather figure that out during a 30-minute phone call than spend a couple of hours traveling back and forth and hanging out with someone that I dislike. I don’t know what “easy conversation starters” means. Small talk? Anybody can do that. Conversation topics are unlimited.

        • noquay Says:

          Yvonne; I agree with you and a previous comment. Sometimes a phone convo can weed out problem children. Weird voice mannerisms, excessive use of profanity, obvious disconnect between alleged educational level and ability to actually speak well, conversation hoggers. I too have limited time and for me, dating requires a lot of driving. However, those that do want to just talk are not worth anyone’s time.

          • Speed Says:

            Apart from their flakiness, “phone screeners” want control, certainty and filters; they don’t want to “waste time (newsflash: everybody has to ‘waste time,’ not only in dating but in life).”

            Moreover, the phone screeners implicitly have a negative view of men as “potential weirdoes or creeps (which speaks more to their bad judgment in picking men rather than men as a group).” They want to interrogate you by phone, have you prove you’re “normal” and worthy of buying them 2-3 drinks.

            WTF?! No, I have enough options that I don’t have to submit to that.

            As an aside, just because a man can hold a 20-minute convo doesn’t mean he’s not a psycho, player, flake, loser or whatever. In fact, those types may be most willing to jump through the hoops just for a chance to get laid.

            Unless you’re Beyoncé, a reasonably successful, attractive, busy man is not going to put his life on pause to submit to your 20-minute interrogation. But a guy living in his mom’s basement might.

          • D. Says:

            Here’s what I don’t get. What’s the big goddamn deal about talking to someone on the phone for 20 minutes? I mean, why is it treated as this horrible ordeal? It’s a fucking phone conversation, not the trials of Hercules.

            I dunno, I think people on both sides of this issue approach it from an unnecessarily militant standpoint, and I really have no idea why. The argument of “I’m not gonna waste my time” appears to cut both ways. Some guys say “I won’t waste my time to talk to you on the phone” while women say “I won’t waste my time to meet you in person unless we talk on the phone,” and I find both positions rather comical, really.

            It’s 20 minutes talking. You can use the 20 minutes to plan the date itself. It’s not about “forcing men to jump through hurdles.” It’s just fucking communication in a nice way that makes the person a wee bit more human than just words on a computer or phone screen. You have a nice quick chat, you plan your date, you go on with your life. Why does either side need to take such a rigid, defensive stance….about a phone call of all things?

            • Helen Says:

              Agreed, people need to learn it’s a part of the process. Get over it. And most of the people who are against phone calls are underestimating its value.

          • Helen Says:

            I agree. I was emailing with a guy that I was willing to find out more about. We moved to the phone and the first conversation he went on a 30 minute rant about his ex-wife. Yeah, like I’m going to want to meet him in person. Some people just don’t get it. And the reverse is true. I have had a good phone conversation with a guy who turned out to be an idiot but this only happened once. I have had way more success talking to guys on the phone first before meeting.

      • Helen Says:

        And that’s why you’re single.

  5. Crotch Rocket Says:

    this went back and fourth with about 14 messages, 7 from me and 7 from her, all within 6 days.
    Well, there’s your problem. Presumably, you’re on an online dating site to date, not to find a pen pal, so your goal is to actually date someone. If they’re not willing to make plans to meet within 2-3 exchanges, it’s time to cut your losses and move on to someone who actually wants to date you.

  6. Speed Says:

    Incidentally, Moxie’s advice here on tips for “first contact” in online dating is about perfect.

  7. D. Says:

    I agree with the folks who say she might’ve been interested initially, but got tired of the endless back-and-forth, at which point it just became something to do to kill time, after which point it ceased being interesting at all and/or she met someone else.

    On the whole, I agree with Moxie’s tips. The only thing I slightly disagree with is the “No questions” thing. I think that one’s a little more flexible, IF you can transition within 1-2 emails to setting up a meeting.

    I’d usually send a relatively brief initial email. Maybe 1 paragraph long, usually remarking on how I liked her profile based on a few specific things in it (rather than just “Hurr durr you has nice profile and purty pics.”). I’d probably mention one or two things we had in common based on the profile, and maybe include one question. Wrap it up by saying you hope to hear from her or somesuch, and that’s it. Longer emails than that for openers are a waste of time and can telegraph desperation.

    After the initial email, we might go back and forth once or twice more based on one or two questions, but once at that point, it’s a safe bet that there’s enough there to chat further over drinks or something. At that point, I’d usually suggest we get together, and that she give me her number and I’d give her a call to set something up.

    In most cases, I found this worked pretty well. A handful of people wanted to just set things up via email, and one or two did so via text, but that was about it. Most of the time, assuming you’re looking roughly in your age group, I found women were perfectly fine with a phone call to set things up. It also offered a chance to make sure neither of you has a super-annoying voice, so, hey, bonus.

    For the record, I’m also in Philly, so that’s based on my non-scientific sample of dating women in Philly and what seemed to work on the front end. People in other cities may differ in terms of how preferred text/email is vs. phone, and how many steps people prefer to take before meeting up, but in general, extended back and forth makes you come across either as a wuss who can’t ask a woman out, or as a guy who isn’t actually looking to date and just wishes AOL chatrooms still existed. Ask her out. The worst she says is no (or nothing in response) and you move on to the next profile.

    • Greg Figueroa Says:

      I say be flexible with questions too. I would focus on making sure you’re not writing a story or spending more than 2-5 mins skimming their profile and writing the message.

      • D. Says:

        Yeah, the real trick with the questions is being able to transition them to actually asking the person out. Like, knowing when to say “Hey, I’m actually kinda busy during the day today, but why don’t we talk more about this over drinks tonight/Wednesday/this weekend?” rather than just treating it as an ongoing conversation.

        The whole point of the email exchange is so that you can eventually meet in person. Unless the person’s profile specifically says they’re only looking for penpals or whatever.

  8. Laura Says:

    To me, the guy sounds incredibly un-self aware. There were so many “facepalm” moments in that narrative that it was almost frustrating to read. Even beyond the 14 messages, the way that it’s so analyzed and formulaic: “I sent a joke, then a self-depreciating (sic) comment, then a why I like your profile, then a question.” You are clearly way overthinking this!

    Without restating all the other commenters (who are spot on), here’s a new thre-step formula:
    1. Send a message, whatever pops into your head.
    2. Repeat with twenty other profiles you like rather than putting your eggs in one basket.
    3. When someone writes back, invite them on a date.
    4. Go on date. Decide if you like them and want to stay on Okcupid, or want to keep looking.

  9. Amanda Says:

    I really disagree about the questions bit. I find it irksome when someone sends me a statement with nothing to go on. Then it becomes my responsibility to keep the conversation going.

  10. chris Says:

    I disagree that conversation consisting of 14 messages with no plans to meet is a clear indicator that one or both parties never wanted to meet. Much of that depends on context and content. Some people exchange a lot of messages strictly because they are either busy and they really don’t trust online dating. They may not be timid in real life, but they may want to engage the person first online to see if it’s even worth meeting at all.

    The content of the messages is also important. Were these long and well thought out or were they short and lacked any substance? Even jokes sent back and forth with various personal information shows that both parties are engaged in the conversation. If the 14 messages were merely a question and answer session consisting of single sentences then I agree wholeheartedly nothing fruitful was ever going to happen with this girl.

    TLDR You can’t just write off a certain style of interaction merely because you do not live your life that way.

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