|I enjoyed reading this. It's a subject that anyone can relate to, and you told the story well. Also, it made me laugh!
I think that with a few minor edits it could read more smoothly, so I'll suggest some:
As a teenage boy, about 16, I had several dates
As a teenager, I'd had several dates ( 'about 16' is superfluous, and the fact that the character is male immediately becomes obvious )
meetings ( 'them' is unnecessary )
important like, dressing properly
important: dressing properly ( colon introduces list )
it was about to
it was going to ( 'about to' is too immediate )
what you could say
what you could call
and wearing a tight fitting knit dress, I was conscious of her full figure.
Grammar alert! This implies that it was yourself who was wearing the dress, oops. A full stop after 'dress' will fix that.
About to crank the window up I tried to stop her but it was too late. With the crank breaking off in her hand I said,
Needs a little tidying up: She started to crank the window up - I tried to stop her but it was too late. As the crank broke off in her hand, I said:
and I was smart enough
and I'd been smart enough ( appropriate tense )
When I was told it was reasonable I was thinking
When told it was reasonable, I had thought (appropriate tense )
Punctuation: either follow 'coffee' with a comma, or capitalise 'but'.
About to spear a cherry tomato in my salad I hesitated.
You form a lot of your sentences this way, which reads poorly. 'I hesitated as I was about to spear a cherry tomato' reads more naturally. It's a matter of syntax; forming sentences the first way can work occasionally, but if you do it too often it becomes intrusive.
Finishing our meal the waiter brought the bill
Grammar: presumably, it wasn't the waiter who finished your meal! 'As we were finishing our meal, the waiter brought the bill'
Quickly doing my duty, I carefully combed my hair
You need to say: 'After quickly etc', otherwise you're saying that you were combing your hair while 'doing your duty'.
Inching towards her
As I was inching towards her ( otherwise syntax doesn't make sense )
"I had a nice evening. good night."
Fumbling with the zipper I was surprised she said,
This needs to be rewritten:
"I had a nice evening," I said weakly as I fumbled with the zipper. "Good night."
I was surprised when she said:
Even though I was called a pervert
There are 2 problems with this. Appropriate tense: 'I had been called'. Also, the construction is passive. Active construction would be: 'Even though she had called me a pervert'.
This is important. Passive voice reads poorly, and writers should avoid it. What is 'passive' or 'active' voice? Well, passive voice describes something as happening to someone, while active voice describes something being done to someone. EG: "The man was bitten by the dog." - passive. "The dog bit the man." - active.
I hope you find these suggestions helpful. I think you have a natural gift for storytelling, and with a bit of work on your syntax ( the order in which you construct your sentences ), your grammar and punctuation, you could be a very good writer. Keep at it!