So, about two years ago I hit OKCupid really heavily for a year and a half. Tons of dates, some morphed into fun but short-lived flings, and then a six month relationship, a couple more flings, and finally The One who I am moving in with in a couple months.

I'd like to think I understand the site and online dating pretty well at this point, so a few pointers:

People frequently stop mid-"conversation". It sucks, but it's part of the game. Usually it's either because they don't have time or they've found someone they're really into and are "done" with the site. The simple truth is that most people are completely self-involved and the moment their needs are filled, they could care less about actually following up with you. You and I might be exceptions to that rule, but it's how most people you encounter are going to operate.

Think of it this way: if they're that self-centered, you didn't want them anyway.

If, as I suspect, you're going for girls in their early/mid-twenties, this problem is going to be worse - they're bombarded with potential suitors, often to the tune of thirty per day (5-10 of whom are creepy older dudes), possibly higher in dense urban areas. Additionally, the stereotype about girls in this age range is true - to a large degree dating sites are a vehicle for filling their need for attention. That generalization about men being far less mature than women until age 20 is pretty spot-on, and the corollary about women being less mature until about age 28 is, well... often accurate. That won't apply to every individual, of course, and it's very important that you not use it as a reason to form a grudge against your target demographic, but it *is* a point to consider when dating online and I find it helps me not take things personally.

Brevity is key - not just of your initial contact (a 30% return rate is standard, 50% means you've got your game down, but don't kill yourself over short term dry spells), but also the duration of correspondence. Keep it to a few messages back and forth at best, and don't use IM - it's better to not walk into that first date with nothing to learn about the other person, or a ton of (inevitably) false preconceptions. Seal the deal early and meet the girl. Hi, how are you, I like this about you, hey thanks for the return compliment, would you be interested in coffee/ice cream/some other casual activity?

The "ice cream" there brings up an important point: learning to anticipate the person you're writing. Assessing people based upon their profiles is an acquired skill like any other. Some girls are going to be happy that you didn't waste their time and just asked them out to coffee in your initial email. Some are classier, more reserved, and you're going to need a couple emails before popping that question. Some girls are going to think you're an idiot to ask them out for ice cream, some will be thrilled. Dinner is almost universally a bad idea for the first meeting - it's a huge time commitment for someone they've never met. Once you've mastered this, you can expect 50-60% conversion of girls who reply to first dates.

Volume is key - send out a LOT of queries. At a 30% return rate, and a 20% overall conversion (initial letter -> actual date) rate, and with you being single, it's going to take a LOT of initial emails before your calendar is anywhere near full. Volume also helps prevent you from placing too much importance on any one person, and keeps you too overwhelmed to sit and fantasize about someone you've never met, which is Certain Doom.

I could go on, but those are the most important things I wish someone had told me early on. OH! DO NOT SEND REJECTIONS TO GIRLS WHO INITIATE. No matter how politely you word it, a significant minority will explode, flag your conversation, your account, whatever. Fortunately, if you were polite the mods will side with you and totally clean it up for you, but "hell hath no fury" is absolutely true. If a girl initiates and you aren't interested, DO NOT REPLY. I had to learn this the hard way, and the mods sided with me because my "rejection letter was nicer than most *acceptance* letters I've seen on this site", but trust me it's better if you don't go down that road at all.

Hope this helps.

posted by Ryvar at 7:38 AM on April 15 [19 favorites]