To start this is going to be a long, somewhat ranty post so sorry about that.
First some background, I know I'm a socially awkward person which is basically why I haven't been on a date in 4 years and has in part lead to me signing up for an online dating service. I used to be completely inept when it came to any social interaction but I've gotten better at it, I no longer have anxiety/panic attacks when going out or talking to people and my job has required me to do some public speaking (mainly large training sessions) which was terrifying at first but I'm actually getting to be pretty good at it now. These are huge improvements for me especially because I haven't taken any medication for the anxiety (I'm not against it I've just never been good at remembering to take a pill every day). I still have a couple problems though like starting and maintaining conversations sometimes, by this I mean if someone asks me a question, that could possibly lead to a longer conversation I drop the ball (generic example: Q: What band is this? Me: Mike Snow, Q: Oh cool (keeps standing there looks like they want to continue talking), Me:....) Basically I give a straight answer to the question and then I have no idea how to continue most of the time. There's also the problem with if I'm walking somewhere (I work on a college campus in the middle of a large city) and someone walking towards me suddenly smiles at me I typically just get confused and if my mind click's and I actually remember to smile back (if they're female that is) my mind then starts to race with what I know/hope are absurd questions like "well (my) smile was creepy”, “Why were they smiling at me is something odd about my appearance" - that leads to me trying to subtly check myself to make sure everything's in order (nothing on my face, no unknown stains on shirt/pants, hat on straight) - or something else along those irrational lines.
Anyway a couple of my friends have had success with online dating and I figured why not give it a try myself, I mean I've got a good job, I'm living in a decent place, and I'm just sick of being single. So I decided on a dating site to use and made a preliminary profile (username, age, gender basically). That was a month ago; I'm not very good at describing myself without thinking I sound like a complete weirdo so I spent that month trying to figure out how to essentially sell myself, which was odd. I also realized through this a couple other things, I don't own a camera (phone doesn't count), I'm usually the one taking the pictures (with someone else’s camera) and that any photo I'm in (damn facebook) I look like I'm either drunk, high, or just a very creepy person, which I wasn't for the majority (drunk that is, I don't do other drugs) and I'm pretty sure I'm not a creepy person (I hope I'm not at least). So I had to ask people I knew if they had a decent photo of me (about that the only good pictures are of me with a hat on, I don't really like my hair in general which is why I wear a hat most of the time to begin with but should I put up a picture of me sans hat?). Anyway yesterday I finally finished the profile and in less than an hour I was surprised to get an instant message from a fairly cute girl. Now of course I'm setting this profile up at work so the conversation was just an exchange of hellos, how are you kind of thing before I had to cut it off to go back to doing actual work (which I should be doing now as well). Which was both a good and bad thing, bad because well I had to cut off a conversation with a cute girl and I didn't write down the username so I have no way to get back in touch with her (doubt she will try again, odd that it happened to begin with). Good though because I realized I'd have the same problem with cold starting/maintaining a conversation online that I do irl and that im session would have been rather short and disappointing for both of us. Not too concerned about the im thing though because it's odd that happened at all and I can send an email to anyone I'm interested in and after that I'm ok with the im conversations. It's the emails that the etiquette question is about, namely what is the etiquette here (for online dating in general I guess)? Is it ok to just send an email to someone out of the blue or are you supposed to "wink" at them first and let them take it from there or is it ok for guys to use the wink function at all? What should that initial email say? Is something to the effect of "Saw your profile and liked that you (mentioned blank). Insert some other question about what they had listed. I'd like to talk with you more to find out what else we have in common" okay to send?
Yes, I could ask my friends who have done this (online dating) about all this but I think that'd be extremely embarrassing and so I find it's easier (and slightly better for my mental health) to just ask strangers on the internet (which I know is extremely weird); plus other questions I've posted on these forums have gotten good advice/info so I figure this is a good place to start. Like I said before I'm socially awkward and I haven't been on a date for a long time but at least I'm trying right? I know I'm probably over-thinking everything but that's just what I do.
To sum up for those who say TLDR - Socially Awkward guy needs help trying to figure out online dating etiquette.
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Also, be prepared to hear nothing back 95% of the time. Women on those sites get inundated with messages. I watched a friend of mine set up an OkCupid account once, and within that evening (3 hours or so) that we spent together, get 50+ messages.
I solved that by just not initiating any messaging while I was on OkCupid. I got enough messages from women to meet some nice girls, go on a few dates, until I finally got bored of it and erased my profile. It feels weirdly unnatural to me. I prefer to meet people under "normal" circumstances, though I can see where the service could be handy it you're socially awkward or don't find yourself in a lot of situations where it might be appropriate to ask people out.
Also, you might want to break down those giant paragraphs a little. They're really difficult to read.
Generally, as a dude, the onus is on you to send the first message. The content of first messages is a frequent topic in the thread I linked. Check it out, pop in there and say hi.
Don't be creepily specific about it (i see you like arrested development I like arrested development lets watch arrested development)
But more of a general, browsed your profile, we seemed to share a lot of interests (name something, 'I saw the white stripes in concert too. What a night. Or something), (link your profile if necessary), if you want to get coffee or something sometime, let me know.
Get her looking at your profile.
But above all, calm down. You seemed very stressed in your op, and being around stressed or anxious people makes me reflect that. You don't want your future date to be stressed out while you're drinking coffee!
Also, if you link your profile, I'm sure we'd be more than happy to help you tweak it!
Remember: confidence is key!