… Date someone you met online (Ok Cupid Part 3)

I’ve written extensively about the mechanics and dynamics of using OkCupid for dating. I’m pleasantly surprised that my previous articles “How to Make an OkCupid Profile” and “How to Write to Someone on OkCupid” are two of the most popular articles on this blog. I figure it’s time to write about actually going on dates, since the whole point of having a profile on OkCupid is to find people to date, right? Right.

So, let’s take it as given that you’ve read Part 1 and Part 2 of this guide, and you now have one kick-ass awesome OkCupid Profile, folks are checking you out, and you’re exchange messages with a few people. If you’re listed as a single bisexual woman (like me) you may be getting anywhere from 80-150 visitors a week. If you are an ‘avaliable’ straight male, the numbers are sadly closer to 5-15 visitors a week. Of course, the more you use OkCupid, the longer you leave it open, the more visitors you are likely to have. Don’t ask me why, but that’s just the way it works.

My experiences with OkCupid in the past three years have been that, for every 10 message exchanges I get in to, I will go on a date with about 3 of them. And once a year- once a year– someone turns up who is a gem of a human being, and I fall head over heels in to NRE (New Relationship Energy) with them and have a positive, enjoyable experience.

Okay, so let’s also assume that you have had some decent message exchanges with people who are using all their appropriate punctuation and capitalization of letters, and you like the vibe of the conversation. What then?

Well, the logical thing would be to ask if they would like to meet up.

It is recommended to make clear ahead of time whether it is a date or not. (you can also buy this thong here: http://www.cafepress.com/polysingleish)

It is recommended to make clear ahead of time whether it is a date or not.
(to purchase this thong, click on the image)


A “Date Zero”, is not about being on a ‘date’.
It is about sniffing someone out, putting pheromones to the photos, and getting a sense of potential chemistry. From there you figure out if this is someone you want to date, to be friends with, or just never see again.

When you are getting in to conversation with someone online, you could jump right to it and ask, after only a few exchanges, if they want to meet up. You get to know someone better in face-to face meetings, and you can’t read physical chemistry from purely online interactions, so meeting up sooner, rather than later can be a good time saver.

On the other hand, I am wary to ask someone to meet up right away in the first few messages. It can feel like too much pressure to some people. Also, how well do you know this person? I’ve had a couple of experiences where I found myself having coffee or dinner with someone who I realized I was absolutely not compatible with- things that would have become clear if we’d chatted online a bit more I’m sure.

For me, I really go on my instinct with this. Very often it is the first message that gives me that impulse of whether I want to meet them in person or not.


Once you decide you’d like to meet up, you need to decide where and when.
Regardless of what scheduling will allow, it is good to get clear with yourself about whether you want to have your Date Zero be in the daytime or evening, be something brief (like coffee) or something more committal (like dinner). Also, you might want to decide if you’d like to give yourself a fixed time frame- perhaps have another commitment to go to afterwards (such as a yoga class) that you can cancel or skip if you find you are really enjoying yourself.

There’s advantages to various types of settings.

  • Coffee: Casual, daytime, low committal, friendly.
  • Lunch: Can be rushed within a workday, but a good way to do something casual with plenty of opportunity to converse if not hurried.
  • Drinks: Open ended, could conclude without too much fuss, could lead in to dinner. I tend to avoid this personally because I don’t enjoy being tipsy around people I don’t know.
  • Dinner: More time to relax and unwind and enjoy conversation.

For a Date Zero, it’s a good idea to avoid anything like an ‘event’. A party or club night, a movie or theater show- these things make it challenging to actually have a conversation. A museum or art gallery might work if you know for sure you have the same level of interest in what you will be going to see- but remember you’ll then be tied in to a whole event with someone, so I think it’s nice to save things like that for a second date. Some of the most fun Date Zeros I have had have involved some kind of refreshment- or gelato- and a walk along the waterfront or a nearby park if the weather is nice.

With Date Zeros, I try to go in with as little attachment to expectations as possible. I am not going for coffee to “meet my soul mate”. I tend to approach it as, “Hey! A possible new friend! Let’s see what they are like!” Of course, there are more “meh” experiences out there than “woah! awesome!” experiences when it comes to Date Zeros. And the majority of people I have met from OkCupid are lovely, friendly, decent human beings, some of whom have gone on to become good friends.


Don’t be coy about what your relationship style is, or what kinds of things you are looking for. If you haven’t talked about it in online conversation, a Date Zero is the time to talk about other significant people in your life (other long term partnerships or ongoing more casual relationships, children, and so forth).

One of the most important conversations for me to have on any date-zero is to ascertain what Polyamory means for this person, and to share what being singleish and polyamorous means for me, i.e. what are they looking for, what am I looking for, and is that compatible? There’s so many different types of relationships that get umbrella-ed under the term “polyamory” that it’s really not as simple as searching OkCupid for other poly folks and saying, “Hey, you’re poly, I’m poly, how about it?”

I encourage you to figure out for yourself what the most significant conversations are for you to have.
For me these usually include:

  • What do you do for work, for fun, etc?
  • What does your social life consist of? Drinking? Partying? Socializing? Geek nights? Fetish nights? etc.
  • What’s your poly-style? What kinds of relationships are you in now? What kinds of relationships are you looking for?



When wrapping up a Date Zero, it’s a good idea to know ahead of time if you would like to hang out with this person again or not- and let them know.

If it is a clear ‘No’, it’s nice to at least be courteous about it. I like to use the “shit sandwich” method, where you sandwich a negative thing in between two positives. For example, “Thank you so much for this exchange. I’m really not feeling a chemistry here, but you strike me as an intelligent person.” I can be painfully shy about telling people this upfront, so sometimes this goes in an email to them the following morning.

If it is a clear ‘Yes’, then you might as well say so! “I’d really like to see you again- what are you doing next Friday? Can I take you out for dinner?”

And, if it is a ‘Maybe’, it is totally okay to sit in that maybe. “I’ve really enjoyed this. I’d like to get to know you more. Can we hang out again?”
Listen to those Maybes. They can be powerful. If you feel the slightest glimmer of indecision about saying No to hanging out again, it is best to end with a maybe, and explore further- perhaps in a different setting and a different time of day. The space of “Maybe” is magical and mysterious, and sometimes the most beautiful connections, friendships, and relationships can arise from the “Maybe”.

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