How Long Should I Message Somebody On OkCupid Before Going On A Date?

Ten messages. Precisely ten. Also, the correct way to introduce people over email.

How long should I message back and forth with someone on a dating site before asking to go on/being asked to go on an actual date?

You know how, when you get crushes on someone you’ve met in real life, you end up feeling like you know everything about him/her too quickly? Embarrassingly quickly, I mean? You have a few chats with some cute guy from work, and he says something positive about your favorite TV show, and suddenly it’s like you’ve known him forever? He’s smart, funny, well rounded, good to his family (and, eventually, yours), feminist, kind, and strong — you are certain these things are true, because you imagine that people without those qualities are blocked by NBC from even watching Parks & Recreation.

You don’t really know anything about this person, but wait. Take away everything you know about his three-dimensionality: his height/width compared to yours, his posture, the way he listens (or doesn’t), his voice and mannerisms. Now you know what you can know from online dating. You’re working with a rough idea of a face and a couple of TV shows. (Or, I don’t know, if you’re on eHarmony, you’re probably working with DNA samples and psychological profiling and are a lot better off than what I’m suggesting.)

With someone you think you might like, I suggest giving it about ten messages total. Some people say three, but I think you ought to give this person a few more chances to totally screw up BEFORE you meet. This is how you save money. If you wait much longer than that, you’re probably going to have a lot of false ideas about what this person will be like, and it’s hard to work with that kind of pressure. You’re going to get to your date expecting a perfect match and he’ll end up being one of those people that sings a few lines from every song or band that comes up in conversation, and you won’t know how to turn down a second date because you’ll think that under that terrible, terrible façade is your soul mate. Save yourself. Ten messages or bust.

So, I often email with the same group of about 4-5 friends, and I find myself always purposely changing up the order of the CC list so nobody feels undervalued. Is this just me? Do I need to do this?

My first instinct is to say something like this: “Yiiiikes! Yikes. If you hosted a dinner party, would you make everyone get up and rearrange chairs every ten minutes so that everyone received equal exposure to each other guest in attendance? What are you going to do if/when you have kids and they aren’t triplets you give birth to simultaneously? What’s next, plucking out your keyboard letters and rearranging them so that the esteemed middle row letters don’t get big heads?”

My second instinct is to take a step back, especially because a lot of those comparisons don’t make sense. Actually, I think what you’re doing is really, really nice. It is very sweet, and also impressive that you can both remember the order you last used and take the time to change that order! I do think you might be the only person doing this. I think you might be that tree stump in The Giving Tree. You don’t need to be so generous as you are currently — most people, if they’re normal and have friends in real life, won’t hold a CC order against you — but your kindness may pay off in the form of getting to have a little boy sit on top of you. It sounds worse than what I mean.

How do I introduce people over email? If I’m putting them in touch to talk about some specific thing, at what point am I supposed to be dropped off the email chain between the newly acquainted people?

What I WISH happened is that right after you introduced two people, in real life or online, you would be yanked out of their presence by one of those large canes that take people off stage, accompanied by some vaudeville music. (If it were online I guess the other two people would see a GIF of this happening.) Actually I want this to happen any time a person wants to be removed from a social situation in which s/he is uncomfortable, or wants to leave but doesn’t know how. Just think how fun it would be to sit in a bar and watch dates all around you end this way!

Fortunately, your situation has an easier out than most bad dates do. You need not bring the proverbial false vomit to take out of your purse in the bathroom, put on your face, and show to your date to prove you’ve become very ill, so to speak. If you construct your email in a particular way, the two people whom you’ve introduced should know to start “replying” instead of “reply-all-ing” and save you from any sort of awkward, inadvertent-fly-on-the-email behavior.

Here’s your magical template. Write “Introductions!” in the subject line. (Maybe don’t use an exclamation point if, for example, one of the two people in your introduction is a grief counselor, a lawyer, a drug lord, or an escort service. I don’t know what you get up to in your free time.) Then write, “[Name], meet [Other name]. [Name], [Other name] is the person I was telling you about who [is selling item/can help with thing/is new to your area/whatever].” Then, on the next line, on its own so it is VERY clear, write, “I’ll let you two chat!” Then sign the email with something like “Have a great day! [Your name]” You (should) have provided your acquaintances with sufficient evidence that you do not wish to be included in their email chain going forward. If they STILL reply all, email “ARE YOU KIDDING ME? Don’t talk to me! Don’t look at me!” Or just ignore it, ugh.

FWD: Halp! is a weekly advice column on how to behave like a person when using technology. Would you like said advice? Email your questions to Katie.

Katie Heaney is a writer and volunteer text message analyst living in Minneapolis. She thinks you should have good manners, even on the internet.

Illustration by Cara Vandermey

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