Ask Me: “When is it a good time to ask someone you meet online out on a date?”


Q: “Hi, I don’t know if you handle relationship inquiries at all, but I had one for you that is specific to OkCupid. A friend of mine who’s been using the site for a while was giving me advice and helping me create the profile, and when he checked in about my progress, I told him that I’d received some messages, but no dates had materialized. I’ve generally been asking people to meet up after the first couple of messages, and he said that’s where I was going wrong.

My issue is this- I am on OkCupid to meet people, in person. I think of this site as the equivalent of walking down the street- you see someone pretty and if its appropriate you walk over, introduce yourself and ask them if they would like join you for drinks sometime. I don’t want to waste a lot of time exchanging messages with people, because I think that the fun of dating is asking/answering all these questions face to face. Also, you get to keep things a mystery that way- where you reveal things but its in the context of “we’re already out on a date…” So, in your opinion, when’s the best time to suggest a face-to-face meetup?”


A: First of all, I think you have the right idea with wanting to “keep things a mystery” and saving stuff to talk about in person on a date. I’ll go more into that later. Regarding the timing of when to suggest a face-to-face meetup: I’d say don’t message back and forth for more than 2 weeks before meeting. But, each person has a different opinion on this, and a different preference. It’s probably better to “feel out” the women you’re messaging, instead of just asking if they want to meet up by default. Take some steps to lead up to the meet up, like messaging > chatting > exchanging numbers. None of these exchanges need to be really long, but at least you’ll know she’s still interested if she’s willing to go to each next step.

Now back to the “mystery” thing. That part of the message reminded me of something from that book I was reading a few months ago, “Marry Him: The Case for Settling for Mr. Good Enough.” I never did finish it, but I bookmarked page 112 because I thought it made a lot of sense and agreed with it. In this part of the book, the author Lori Gottlieb goes to see a dating coach called Ariely, and they’re talking about online dating.

I told Ariely that when I’d done online dating, I always wanted to get a lot of information up front so I didn’t waste my time. In fact, I wouldn’t respond to profiles if they didn’t have enough information. Was I doing it all wrong?

Ariely said yes: Knowing too much about a person sight unseen makes it harder to become interested in him…. The less you know about a potential mate before you meet, the better. It leaves room for a fantasy to build. When online daters meet in person, they have so much prior information that there’s little room for discovery. And once you see a flaw in the other person, the fantasy is ruined. So instead of giving the person a chance, you go home and log on to the computer to find someone else who looks good on paper.

There are a bunch of other articles about online dating that basically say the same thing. I know this was not part of your question, but it’s good information to have. Basically, don’t give your life story out before you meet the person. There should obviously be enough interest between the two of you before the initial meeting, but there should also be a lot more to discover about each other on the first date (and hopefully future dates). Piquing another person’s curiosity about you is really, really important. That’s part of what the “Show, Don’t Tell” section in How to make your OkCupid profile interesting and readable is about.

Good luck!

One Response to “Ask Me: “When is it a good time to ask someone you meet online out on a date?””

  • Felix Says:

    I actually met my wife on okcupid, so it does happen! But I just wanted to add my two cents that I would usually ask for a number and a meetup at the end of my third or fourth message; something like, “blah blah blah…Hey you seem pretty fun and normal; let’s meet up for a drink or some coffee. What’s your number? Mine is xxx-xxx-xxxx.”

    I also always signed my real first name at the end of all my messages so it kind of established I was a real person. I think waiting too long to ask turns your interaction into an “online only” type thing.

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