I spent almost a year of my life on OkCupid, managed to get a decent number of dates for my effort, but I doubt I will never try it again. Online dating poses two particular challenges over meat-space dating:
- The people who are inclined to engage in online dating seem to be shier than average. Combine this is the fact that there are a lot of "colorful" characters on online dating, and they are hesitant to meet in person even if there seems to be a connection. Consequently, you end up talking forever before you finally meet them. The problem with this is twofold, one you find out too much about them, and lose out on a lot of the mystery that keeps the first few meatspace dates interesting. You also build a relationship of sorts, it's impossible not to with several weeks of writing letters and engaging in chats. Now when you meet them and it doesn't click you've got a much harsher let-down than you otherwise would for a first or second date.
- There seems to be an above average percentage of people who misrepresent themselves. This is hardly unique to online dating, but it's easier to filter a lot of it out when you can meet in person, look someone in their eyes, watch their vocal inflictions, etc.
I think I landed eight or nine dates on OKC in the time I was there. Probably half of them were normal, just didn't click, the rest had issues ranging from "completely misrepresented herself" to "was lining up dozens of guys for dates" to "thought we were married after two dates". I tried it for all the usual reasons, not really into the bar scene, don't have a whole lot of free time, and so on. If I were to try it again I would insist on a meat-space dates after a few good conversations. I do understand the safety issue, particularly from the female perspective, but someone who isn't willing to meet in a busy public place for lunch is likely too shy/introverted for me, or is trying to play games.
Incidentally, the last woman I went out with I met while on a run. She's out walking her dog, I'm doing road work, we wind up talking and the rest is history. Thinking back on it, I had my most successful relationships with those that I met in situations where neither of us was looking for dates. It's just easier to be yourself in that kind of situation, I think, and you're more likely to sustain a relationship with someone if you were yourself from the beginning.