Lets see if i can answer some of these:
1:The problem was that they didnt escalate properly, they both reached a point where they would usually focus on one girl and escalate to a kiss close but they had two girls sitting there and so they didnt know what to do. and as a result the girls got frustrated/bored, and they had to bail.
2:Did you not watch the rest of the series, they shwo many times how to seduce a girl in a bar or club.
3: Ha! for me? i'd say alot is down to the girl. Often i cant break through that last minute defense which stop women from wanting to look like sluts. But find a slut anyway, and you're home
4: Same as above, this was shown several times, most important, i feel, is Kino escalation. Get her comfortable with increaing levels of contact and intimacy, then thshe'll be confused/dissapionted if you DONT go for the kiss (as seen in one of the episodes with the bill gates look alike where he has a chance at a 3-way kiss and legs it!)