1. Meet sooner rather than later
You're both ostensibly online dating to find someone to actually spend time with in "real life," not to message back and forth for all of eternity. If after two or three message exchanges the person you're chatting up seems cool and normal and at least semi-literate, suggest meeting up.
2. Make it a real date
Forget the nonchalant, "So, wanna hang out?" ask-out cop-out. You're online dating to find love (or sex), not a new pal. So ask the object of your Internet affection on a real date, with a suggested time and place. Make it an event that's easy to end early if it's terrible, but also easy to extend if it's wonderful (this is why coffee or drinks are the go-tos; plus alcohol makes everyone a little more comfortable). Definitely make it somewhere public: "Come over to my house for a glass of wine" is clearly a line from a murderer.
Do not ask an Internet stranger out on a dinner date for your first meeting. Do not invite an Internet stranger to hang out with you and your friends on your first meeting. Do not invite an Internet stranger to do something that involves watching you perform with your band/improv group/traditional Polka dance team/whatever. I'd even advise against something like a movie, since you can't talk and actually get to know each other.
3. Remember your manners
Just because this is an Internet date doesn't mean you have an excuse to behave any less well than how your mama raised you. Be on time. Leave your phone in your pocket. Definitely don't be tweeting, Facebooking — or checking OkCupid — while you're out with your new interest.
And if you're the one doing the asking, then you should do the going — to their neighborhood, or somewhere convenient for them. You should also be the first to offer to pick up the check. They may insist on splitting the bill and that's fine, but whoever actually asked the other person out should be the first to offer to pay.
4. Keep the bad behavior to a minimum
So your date shows up and you realize their photos weren't exactly accurate. Or they laugh like a hyena. Or it turns out that they're completely vapid. Your response? Be nice and polite and make your exit after one drink. Your response should not be to toss back five or six drinks and get wasted out of sheer misery; your response also should not be to exit the date before it's begun, or to tell them exactly why you find them unattractive or uninteresting.
5. Have a stable of good stories
Dating is kind of like going on a job interview: You need to know how to sell yourself smoothly and efficiently. Have two or three tried-and-true funny stories on relatively neutral topics (no exes, no sexes) and tell them at appropriate times. Have a few standard getting-to-know you questions, and follow up like you're a good reporter. Don't interrogate, but do ask more than, "So what do you do?" Definitely do not use the date as an excuse to get on a soapbox and talk about yourself and your own views the entire time. Take a step back and make sure the conversation is roughly 50-50. Also be sure to keep the super-personal out of it. If there are relevant details that need disclosing (you have a kid, you're moving to Indonesia next week), disclose those. But there's no need to be totally up-front about deeply personal issues (you're an adult bedwetter, you once pooped your pants on live TV).
Dating is a skill, and it's one that gets better the more you do it. So whether you're interested in getting married or just getting laid, go on a bunch of dates with a bunch of different people. Cast your online net broadly, and go out with a diverse pool.
The more you date, the better date you'll be. You'll hone your conversation skills, figure out which topics and stories work and which ones don't, and learn what you like about talking to complete strangers. Even if you don't hit it off with everyone you go out with — and you won't — the experience can be heartening if you frame it in the right way. Think: There are all of these interesting people in the world with X, Y and Z good qualities, and even though most of them are not for me, they exist in large enough numbers where one of them will eventually be the person I click with.
7. Once you actually go on a good date, follow up quickly
None of this "three-day rule" business. If you had fun and you want to see the person again, get in touch the next day to say so. A text message works just fine, and is better than keeping the convo on OkCupid.
8. If you don't hear back, move on
Not every date is going to be a winner, and sometimes you'll go out with someone you like who doesn't feel the same way (and vice versa). If you had a good time and you followed up the next day and your date is MIA, don't sweat it. There are literally millions of other people dating online. The worst thing you can do is to bug the person for a response, or demand a reason why they don't want to go out with you.
Sorry, but you are not entitled to know why a complete stranger doesn't want to hang out with you for a second time. So let it go. On the other hand, if you're the one who doesn't want to go out again, the polite thing to do is to respond to the follow-up with a kind rejection. Something along the lines of, "I had a really nice time and it was great getting to know you, but I just don't think I'm feeling much chemistry here. But thank you for the drinks and good luck!" should do the trick.
9. Keep it breezy
You just went on a date (or a few), and things are good and you're realizing that maybe this could be A Thing. Don't get too ahead of yourself. You're both on an online dating site, so you're both probably actively dating other people. Don't stalk their profile to see when they've been on.
Give it at least a few weeks of regular dating to bring up the "So should we shut down our online dating profiles now?" conversation. It can be really exciting to finally meet someone you like, but you were strangers not so long ago, and unlike in a more traditional dating scenario, you probably don't have mutual friends or even acquaintances who can vouch for the other person. Take it easy and actually get to know the object of your affection before you're taking a road trip to Match.com headquarters to get a free "We were Matched!" t-shirt.
Good luck, happy dating, and please invite me to the wedding.
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