Did these involve bars and public gatherings?
I don't go to bars. Ever. Both my parents were alcoholics, and I'm not comfortable around a lot of people who are drinking, especially if they've gotten to the stage of actually being drunk.
Public gatherings depends on the type. I'm comfortable at moderate-sized science fiction conventions, where it's pretty much guaranteed that no matter who I talk to, we'll have at least one thing in common, be it an author, favorite TV show, movie, a character we both like, or a common interest in writing, filking, or type of reading. That's not to say I haven't met some jerks at such gatherings; one of them had a habit of coming up behind women and rubbing their backs, and he never asked permission. The first time, I just moved out of reach. After the second time, I said, "Please don't do that." The third time, I told him off in front of everyone, in the middle of the main hallway on the mezzanine where most of the programming was going on. He got defensive and said that "everybody else likes it"/"nobody else told me they didn't like it". I reminded him that I had already politely told him to stop, and he hadn't listened. Thankfully he did stop this time, or my next step would have been to have a chat with the security people.
I'm not usually a partying person, for several reasons. As mentioned, I don't drink and am uncomfortable being around a lot of people who do. The only exceptions I ever made were for the techie and production parties that went along with working in the theatre. I figured I did my share of work, and deserved a supper and entertainment like everyone else. But the whole dressing up, preening and primping? Nope, not my thing. I'll fuss over a costume for a convention until it's "just right", but an ordinary party, never.
A lot of these conversation involve the girls spending more time laughing than talking. Maybe they're attracted to the guy anyway and just fake it?
I honestly couldn't say. It's true that some women are fake, and that some regard social settings as just a game and don't consider the other person's feelings. Keep in mind that with some women, they're not out to impress the guys. Their motivation is competing with other women - who has the more expensive or exclusive clothes or accessories, the latest hairstyle, the most fashionable makeup, and who can attract a man.
But there are plenty of women who are not fake and shallow like that. This is why I suggested getting involved with some community group or volunteering. That way you'd get to meet people when they're not trying to impress others, and are more apt to just be themselves and you have a better chance of figuring out if they're someone you'd like to be around more, and work up to that long conversation you're looking for.
Most of my social experiences come from the theatre, science fiction conventions, the Society for Creative Anachronism, and small gaming groups. Only the theatre people were into what I would consider "mainstream" socializing - going to a bar, dressing up, dating - to someone who preferred to sit back and observe, it was fascinating to see which people became couples and then later broke up and/or exchanged partners with other couples, almost like a real-life soap opera.
This brings up the issue of whether or not to pursue someone who is already in a relationship. I've never done that. If I know a guy is married or in some other committed relationship, then my interaction with him will go no farther than casual, friendly conversation about some topic we're both interested in, or just participating in gaming with a group of other people.
If I've ever had a conversation I've felt 'comfortable' in, it's too far in the past to recall.
Think of a conversation you've had on CFC that you've enjoyed. Can you picture having that conversation, or a similar one, with someone you're with offline?
That's another typo. I mean that I don't find them interesting.
Okay. Most people tend to find common ground somewhere with these topics. Mind you, sometimes it's a spectacular failure. I've got several
dozen people on my ignore list at TrekBBS because of how they reacted (trolling and flaming over a period of
years) because I don't like the current crop of Star Trek movies.
But that doesn't mean you can't find common interests with people in other areas.