OkCupid Dating Tips

I got into a discussion on a poly list about how online dating services develop specific rituals, and if you deviate from these, it often means no dates. I wrote up the following advice list for poly men who are looking for poly women on OkCupid, which is the situation I am most familiar with.

Your mileage may vary, and probably does. I would love to hear about what works differently for you, especially if you are in a different gender search arrangement.

And here’s the list:

Expect rejection from women in the form of silence and do not be phased by it. Do not send angry follow-up notes. Do not take it personally – maybe they’re just not looking right now. My personal best was 1 response for every 5 messages I sent out, and I’ve seen 1 in 20.

To balance this out, most guys send to a decent number of women. I would say that if you are seriously looking, you should find two to five women each week whom you are very attracted to, and send them good messages. If you run through everyone you are attracted to in the area, then just wait and re-check the site monthly.

A good introduction message is neither too short nor too long, maybe 3-8 sentences. It should make it clear that you read their profile, by discussing interesting things you have in common. If they state that only certain people should write them in their profile, never violate this – you’re wasting your time.

Messages on dating sites to women should not be sexual or contain come-on-like content. You should not try to take it off the site (to phone, email, IM, or in person) in the first three messages. Waiting for her to make the move is not a bad idea, though some women never will. Waiting longer than two weeks is probably a bad call. If and when you do ask to take it off the site, give them the option to remain on the site if that would be more comfortable. Instant message is a good first step, because that way you can communicate a lot with no investment. Do not IM women out of the blue on the personals site.

In-person meetings are generally for coffee with only a half hour commitment or so, giving either party an easy out in case the chemistry is dead. Do not assume that a first coffee date implies a second real date – always request a second date. In general, acting entitled at any point will get you shafted.

OkCupid is very focused on match percentages, so you should answer 500 questions to get those percentages up. Focus on people at 90% or above – the matches really work. People will often reject folks out of hand whose percentages are lower than 80%. To get past the stony wall of silence, OkCupid has a number of icebreaker mechanisms (QuickMatch, Quiver, IceBreaker, etc). Use these in a playful manner – “You landed in my Quiver and for once it delivered me someone really neat” is a great opening line.

A good profile is very important. It should have pictures of you, good ones that make you look good. Guys should stay clothed and have face shots. Pictures that are interesting are a lot more valuable than pictures of you standing around. Fill out the profile in a playful manner, giving lots of details about yourself and keeping the content interesting. Do not be shy about your good qualities, but avoid coming off as arrogant. If there are cool things about you, be sure to put them in, especially if they help people find out a lot about you. I.e. if you blog, post a link to your blog.

Use the journaling feature of OkCupid to add further interesting content on a regular basis. Commenting on the journals of people you are attracted to is a great thing to do before or after you send them that first message. In general, anything you can do to show them that you are interested in them as a person (rather than a series of orifices) is a good thing to do.

Do not post laundry lists of what you are looking for in person, especially if these things are shallow (i.e. blondes). However, do be very clear about what you sort of arrangement you are looking for – my profile currently says that I’m only looking for casual play, for example. Do not post your STD status in your profile, but if you have something, make sure to say so while messaging or on an early date, in a “is this going to be a problem?” kind of way.

There are a lot of poly-specific concerns as well. State that you are polyamorous and mark poly/polyamory as a keyword. If you are in a relationship, make sure your OkCupid status says “available” rather than “single” or “seeing someone”, and say who the other person is in your profile, possibly linking to their profile. Be specific about what sort of poly situation you are looking for, unless you are flexible, in which case you should state that in a way that prevents people from assuming things about you. Of course, if you need to stay closeted, none of this applies.

People often look for polyamory or poly-style arrangements without using the word. Hunt for people who are “available”, or who otherwise indicate nonmonogamy in their profile. People with very high match percentages to you (high 90’s) are likely nonmonogamous as well – take a chance on some of them.

If a woman writes you, she’s interested, unless she specifically states otherwise or is asking about something unrelated, like where to find the nearest poly gathering. Be flattered, but otherwise do not deviate from the above. Women writing you is a good way to judge your profile – if it never happens, your profile may need work. If it happens even infrequently, your profile is probably pretty good.


  1. Dear Pepper,

    You always impress me with your thoughtful, evolved, and gracious understanding of human interaction. Thank you for posting this primer for men using OKC: I think the people who run the site would be wise to post your tutorial as well!


  2. I’m posting it on my OkC profile! 🙂

  3. I have had very good experiences with okcupid. It’s how i met my OSO. Also other interesting like minded people. If i may add something to your list of tips, it’s this:
    Try not to look for caramel, but for sugar. Meaning, look for potential open mindedeople who might find polyamory interesting, even if they don’t identify as polyamorous.

  4. […] https://poundcake.wordpress.com/2010/09/16/okcupid-dating-tips/ This entry was posted in Uncategorized. Bookmark the permalink. ← taking risks and being open to other people. LikeBe the first to like this post. […]

  5. Great post, never heard of okcupid before.

  6. What excellant advice not just for OKC but I would say any dating website.

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    • Sorry, I don’t do reviews or guest posts.

  8. […] overview of the site as well as some helpful tips for prospective poly daters. Poundcake has some great tips for poly men and there are some more general poly tips […]

  9. […] overview of the site as well as some helpful tips for prospective poly daters. Poundcake has some great tips for poly men and there are some more general poly tips […]

  10. There is sound advice here for all OKC users. I just linked it on my blog , “Dating Tips From Satan” ( http://iblyss.wordpress.com). Nice work!

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