Oh, man, you massacred that date!! LOL
Anyway, you seem as a genuine person, have written this article at least, pointing that you have thought on the subject. I guess that counts for something, NOT being a total jerk after all. :)
Everyone makes mistakes, but first impression mistakes can be costly. Well, in my opinion, the girl didn't have much of a sense of humor (speaking strictly through your eyes and impression from this date). Did she say anything funny? Did she ask you any type of questions to better get to know you?
You see, in dating it's not a game played ONLY by one party (male), a man can be a leader, true, but it's a TWO-WAY-STREET! Like a dance - you say something, she catches on that and answers, conversation evolves. From what I read I didn't note she was that interested in "breaking the ice" or doing a lot of effort for the date to be successful (AND that means TO BE HAVING A GOOD TIME!! - nothing less, nothing more!) :)
(BTW. that condom comment was not the best in time and circumstances.. sex comments would be a TOTAL turn off for females, especially on a first date, especially as a first kind of a line, haha!). Some type of intelligent people really don’t have tons of sense of humor and their perception of the world is a bit more on the serious side, to which you may seem childish, foolish, negligent and careless .
Bottom line is to "feel" the other person, his/hers mood and willingness to play along :)
Best of luck next time!