Puckmarin's Guide to Online Dating
Background
I met my wife via OKCupid in July 2011. We were married in Dec. 2011. We only dated for 3 of those six months. After dating for 3 months she dumped me to get back together with her ex. We remained friends and became best friends. Sometime in early December she realized that she was madly in love with me and just had to be married to me. She let me know this the Tuesday before Christmas. We were married in a courthouse wedding a week later and things have been great ever since.
I went from being totally single (with her dating the other dude) to being married in a week. It was awesome.
True Story.
Here's a picture from the wedding:
Prior to falling madly in love with my wife and spending September - most of December in a deep depression I engaged in a lot of online dating. If I wasn't dating someone regularly I'd have at least one or two online dates every weekend. Sometimes both in the same day.
Advice (Take this with a grain of salt - it worked for me it may or may not work for you)
1) ALWAYS be honest and truthful in your dating profile. This also means posting accurate pictures and answering all of those OKCupid questions accurately.
2) Quickmatch is your friend. Once you have your profile set up use it. Rate women/men. Rate lots and lots of women/men. Sit down on the couch, start a movie on Netflix, and start rating people. Rate every woman/man in your geographic area. If you're the least bit attracted to them give them 4 or 5 stars.
Why?
The idea is that some of the women/men you rate highly will also rate you highly and you'll both get a cheesy introductory "you should email this person" email from OKCupid. At this point OKCupid has done some of the work for you. Email these people because you know there is at least a little attraction there.
3) Online dating is a numbers game. The more people you contact the more people could potentially write you back. Think of it this way - if you contact 50 people you are attracted to you may get 20 replies. If you reply to those 20 people, 10 of them might send you a second email. Of those 10 maybe 3-4 of them will turn into actual dates. Therefore, contact as many people as you can.
4) Regarding messages, I always found it useful to keep the message sort of short. Maybe a paragraph addressing something in their profile (books, activities, pets, etc...) and then a short paragraph about yourself. Make sure you leave some questions in there so that the person you are writing has a reason to write you back.
5) The whole point of online dating is to actually meet someone in REAL LIFE. Therefore, it's in your best interest to get communication away from OKC and to the phone/text as soon as possible. My rule of thumb was that I always gave people my phone number in the second message. This is also the message where I'd normally turn the conversation towards meeting up.
If I contacted someone during the week I'd always try to set up a date for that weekend. Sometimes even for later in the week if we could both agree on a night. There's no reason to waste your time on people who are hesitant to meet in person.
6) Along with #5 I always tried to keep communication to a minimum before physically meeting someone. My wife and I only sent a couple of text messages back and forth before meeting.
Why?
Lots of communication before a date tends to raise expectations and that never works out well. In all my experience in online dating the dates where I've talked to people a lot beforehand have never really worked out well. However, the dates where I've barely communicated with people always seemed to work really, really well.
7) Pictures - make sure they are accurate. As I said in another post, I don't photograph well. I always look weird. Anyway, I always put up pictures that weren't the greatest. Thought being that if someone was attracted to those they would certainly be attracted to me in real life.
8) The internet makes people weird. Online dating also makes people weird. Expect to encounter some odd people out there. Roll with it. It's only a date.
9) It's ONLY A DATE. Even if you aren't 100% sold on the person you are going to meet up with go out anyway. Worst case scenario you're out a bit of cash and a couple of hours. Who knows, you may hit it off with the person.
Finally...
10) Don't sell yourself short. If a person agrees to meet up with you then they must be attracted to you on some level. It took meeting my wife for me to realize this. First date we met for lunch. I walked in, saw her and was blown away. Super hot, lots of tattoos, totally not the type of woman who would normally go for me. All though lunch I kept telling myself that there was no way she would be interested in me. Well, lunch turned into a 5 hour date (which we both agree was the best first date we had ever been on) and 6 months later we were married.
About first date activities. Keep it simple. I always liked dinner & drinks (alcohol always helps everyone) or maybe coffee. Don't try to be too creative on the first date. Save that for later.
Hope this helps some people. Feel free to ask any questions you might have.