Feels like people are making it seem that online game is somehow inferior to offline. Which is true to a degree, but in my opinion irrelevant. I don't think you need one in order to be capable of the other.
Anyway, OP:
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In both those cases where I almost had sex with the girl, there were sexual plans or suggestions we made in the initial exchanges of messages and texts before meeting up. The vast majority of girls I date don't exchange any overtly sexual messages with me before the date, so perhaps that's part of the problem. Most of the girls I've dated seem to be more the LTR type than the hookup type, which would be fine if they were interested in a LTR with me but clearly they're not.
Stop trying to label a girl before you know her. There's plenty of normal, "LTR" type girl that only want to have their brains fucked out by a proper dude. You'll miss out because of your current mentality.
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1. Maybe kissing the girls or touching them too much (or for too long) on the first date is a bad idea, and I need to dial this down. After reading blackdragon, I've decided to stop going for the kiss on the first date (I kissed girls on the first date as a rule for a while). We will see if this works.
I never heard of blackdragon but I dislike him already. There are very few cases where not kissing her on a first date will pay off, and even in those cases the payoff barely outweigh the risks.
Kiss girls on a first date. Just don't do it at the end like every other clichee ever. Do it during, on highpoints, where you're really enjoying yourselves.
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2. I am only 5'7, and I generally wear height-increasing shoes on dates, they make me look two inches taller. On websites where it lists height, I put 5'9 (Tinder has no height requirement so I don't list it there). Is this a good or a bad idea? Can girls tell that I'm faking it? For instance, because they can hear the "high heel" type sounds the shoes make, or I walk a bit weirdly, or because when I sit down I look a bit shorter. Also, when the eventual time comes where I have them in a home situation and we're together (making out/watching a movie/having sex, whatever), when the tall shoes come off, are they gonna view me as dishonest?
Would it be better to just eschew the tall shoes altogether, put my real height up, in order to avoid girls potentially seeing me as dishonest and insecure? I'll probably get less dates this way, but may it also mean a higher chance of attaining successful dates?
This is ridiculous. Of-course they'll see you as insecure, because you are insecure. Look at you. You're worried about the heel noise you make and how you appear when you sit down. Change the things you can, own the things you can't. You can't change your height.
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3. I take ADHD medication (Concerta). I have taken similar medications for most of my life, but I've been off them for the past five years, up until I started taking it recently, a few weeks ago. I don't know if it's helping or hindering me. I feel it stops me from blurting out stupid comments, and it makes me feel more attentive and self aware in general, but it may also make me seem less funny and spontaneous and more robotic. Then again, perhaps being too obsessed with seeming funny is part of my problem when off the pill to begin with (and to a lesser extent, when on it), and maybe this change in behavior is for the better? Also it seems to make my penis and testicles smaller, definitely when flaccid, and it's hard to tell but it may also do the same when erect.
I never was a big fan of medication. That said, I only take it when it's absolutely necessary. Also I'm no MD so the seriousness of your ADHD is not something I can speak on. I highly doubt it makes your dick smaller though.
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4. I live in Toronto...terrible city, I know. I've read all the PUA articles about it. I try to date girls elsewhere in surrounding cities though, because I am in a different smaller city about an hour's drive away, on weekends. Does anyone here know if the terrible aspects of dating girls in Toronto also apply to the other surrounding cities like Hamilton, Kitchener-Waterloo, Barrie, Guelph, Cambridge, etc.?
You're telling me that all the girls in Toronto are somehow un-dateble? Stop making excuses
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5. Given that I live in the Toronto area, how seriously do I need to avoid saying anything politically incorrect? I try to avoid politics as much as possible on dates, but sometimes I feel like I blurt out the wrong thing. The ADHD pill lessens this problem somewhat, but not wholly.
Is it really important to make a girl laugh a lot on a date? If being funny runs the risk of inadvertently offending her, is it better just to avoid any joke that even stands a remote chance of pushing those bad buttons?
How much are girls typically offended by anything even remotely offensive? (ie anything possibly interpreted as sexist, racist, ableist etc regardless of whether it's a joke or serious). I read on blackdragon, if you say ONE thing that hits the "offended" button, that's it, you're done, game over. Since I get a lot of first dates but few second dates, could this be my core problem?
You don't need to avoid saying anything. It's generally a stupid idea to talk about religion/politics on dates. But political correctness is retarded in my opinion. I mean your underlying problem is obvious. You're a pleaser. You put the entire female gender on a pedestal and feel you need to prove yourself to every girl you date. That's where your obsession with "not saying the wrong thing" comes from. If you dated a KKK member, she'd love you "political incorrectness".
Personally I don't care about your values and I'm not here to talk about them, but the point I'm trying to make is that you need to search for compatibility, instead of trying to mold your own persona after every single woman you meet. Also, again, fuck blackdragon.
No it's not important to make a girl laugh. You're not a clown. This question springs from the same pedestalization thing you have going on. What's important is to have a good time. To have an enjoyable date.
For both of you. Whether it's through humor of philosophical threads of conversation is irrelevant. Personally I value humor, witty conversation and teasing. So I get along great with girls that share those values. I'm also highly incompatible with easily offendable people. Which is perfect, because I wouldn't enjoy nor want to spend time with that kind of person.
Finally, how much they're offended by certain topics varies greatly. If you're playful you can get away with a lot of things, but again, not everyone is mentally capable of recognizing that. What's most important is your intentions. If you make a humorous racist comment because you find it funny, the intention is positive. If you make a racist comment because you are a racist, the intention is negative. And so will be her reaction.
I feel the need to stress this out for you. Stop being obsessed with pleasing people. It makes you look as if you have no identity of your own. You're like water, taking the shape of any given recipient it's being poured into. That's not sexy.
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6. So far for me, the copypasta pickup line first message approach on online dating sites hasn't seemed to work. I have a bunch of funny pickup line first messages, but every time I've tried mass messaging girls with it on POF, I haven't got any real results. Maybe on Tinder that sort of thing would work better? I usually try the more conversational approach of opening up with a "how's it going?" and a reference to something in their profile, often a joke about something in their profile if I can think of one.
"Hi <name>, my netflix is broken. Can I come over and watch yours?" I've been using that for as long as I can remember and for the majority of the time it gets positive responses. It's a funny line with cheeky implications.
I'd never go for "how's it going" though. I absolutely hate being asked that type of question myself, so I won't do it to others.
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7. I try to talk a bit about sex during every first date, but often we don't talk about it much during or before the date. And if we do, it's often in a rather chaste context without going into too many details. I find at bars, when other people nearby could be listening, it seems awkward to discuss sex in a more detailed way. Is that a problem? Should I be more aggressive in talking about sex more?
You can talk however you want, just don't be thirsty. If you act like a horny pre-pubescent teen when talking about sex, yeah, not cool.