Message first. The general rule when it comes to finding people you’re interested in is “if you like them, let them know.” You can’t just wait for them to come to you, and besides, online dating is supposed to strip away all of the anxieties around “I don’t want to be the one to make the first move.” Act on your interest, and send them a message before the cold, hard algorithms tear you apart forever.
Never use tired lines. There is nothing worse on OKCupid than receiving some cornball pickup line that you know they have used on approximately 20 other people that day alone (I’m looking at you, 20-something dudes with mirror selfies as profile pictures.) If you’re actually into someone, you have to say something genuine to them, even if it’s just “Hey.”
Be honest about the pictures. Look, it’s a cold reality, but be honest with yourself about how much their pictures actually interest you. Don’t go on a first date with someone you know you’re not going to be attracted to just for the sake of doing it. Part of your initial connection, just like if you met in real life, is going to be physical attraction, whether we like it or not. And if you’re getting the vibe from their bizarrely-angled photos that you’re not going to be into them, don’t do it.
Read the entire profile. Make sure to scroll all the way to the bottom and soak in everything they have chosen to say to the world. (And while we’re at it, an eerily empty profile is just as bad as one filled with MRA rhetoric or misspelled ethnic jokes. Empty profiles means ‘functionally illiterate and/or just looking to hook up, which is the opposite of trawling OKC for actual love.)
Be sincere. It’s so easy on online dating sites to flatter someone, or pretend to be more interested than you are, or carry on long exchanges of tedious small talk just because, hey, it makes you feel good to see a message in that inbox every morning. But part of the deal is that you have to be extra sincere, especially since “just walking away” is not an option behind a computer screen.
Be open with what you want. If you’re looking for an actual relationship, make that clear in some way. It should be assumed, but it’s not, and a fair amount of people are just cruising the sites for sex or casual dating because (I assume) they have not yet heard of Tinder. You don’t have to say it in the first message you send, but making it clear in some way what you are looking for before, say, the second or third date is really important.
Have a phone call first. The best way to tell if you’re going to hit it off with someone in that first IRL date is to have a phone call. Do you have chemistry on the phone? Do you make each other laugh? Does the conversation flow easily? If not, you can probably guarantee the same dynamics on your awkward first date at the coffee shop.
Pick an easy first date. And speaking of coffee shop dates, it’s incredibly important when deciding where to go on the first date that it be somewhere public, casual, and easy to leave if needed. Yes, part of it is that you never know what kind of creepers you might be agreeing to go out with, but part of it is also just “keeping things low pressure in case the chemistry isn’t there, because you don’t want to be stuck with them for five consecutive hours.” Something like a coffee shop, or a happy hour drink, are the perfect settings for this.
If it doesn’t work, be honest. If you don’t want to see them again, tell them right away, and be as blunt as necessary. Don’t leave them even slightly unsure, because that will mean a barrage of messages on the site for the next 2-3 weeks, or until they fully get the hint.
If it does work, follow up. When you do find the right person, though, you have to be equally open about your interest. Think about it: You’re both on a website where ~*~The Next Love Of Your Life~*~ could message you at any moment, and you project an “extremely single” vibe to the world. If you want to start seeing someone seriously, let them know, and try to do it in person (because you’ve both had enough romantic communication from behind a screen.
Close down your profile when you know. When it gets serious, close down your profile. It should go without saying, but some people strangely leave theirs up, and then continue to receive boldly flirtatious messages for the first few months of their relationship, which is just something no one should be receiving.
Be honest about how you met. For so long, I lied about where I met my boyfriend, saying that we met at Starbucks (??) because the idea of telling my grandmother or, worse, his grandmother, that we met on a dating site felt at once geeky and tawdry. But this is 2014, and everyone is meeting online, and if someone is going to judge you for something like that, they’re an asshole you don’t want to be associating with. Be honest, and help erase the stigma.
Spread the good word. I recommend OKCupid to my friends all the time, because even though you will get messages from married 41-year-olds asking if you like feet, you will also meet a ton of great people you never would have come in contact with otherwise. And in our constantly-expanding world of quick-dating options, OKC feels practically old-fashioned. It’s a chill place full of chill people, and if you follow the golden rules, I guarantee you will find someone truly great. 
