Dating Pains

Hey There:
I'm starting to debate if I should be back in the dating scene, I may not be ready yet. I've been on two dates and I don't know if it's just normal dating pains or me still picking the wrong type of guys...again!
I went on a coffee date with an Indian guy, as I expected I got there on time and he was late (30 minutes). I was about to leave when he arrived, making some excuse about leaving his phone at work (what does that have to do with being tardy?) and as usual I was way over-dressed.
If I go out to do errands or do some tourist thing I dress casually; usually in cotton dresses with little or no make-up and my hair in a pony-tail. When I meet someone on a date I give it a little extra: a nice dress, high heels, I do my hair, make-up and add accessories. I want to look nice for the first impression, but the guy arrived in jeans and a very faded orange Crush soda t-shirt.
I was actually looking forward to this date, we had been texting and e-mailing for days, he seemed like an interesting guy and looked OK on his pics. None of it translated well in person and then unknowingly he made another mistake. He asked me the hated question "So, what do you do for fun?" I feel I've been asked that question hundreds of times. I absolutely Hate that question!
Why do I loathe this question so much? Because by the time it comes up I already mentioned what I do for fun. So they either didn't pay attention to what I said or have nothing better to talk about.
So to re-cap: he was 30 minutes late, came dressed very poorly and asked The Question.....Next!
Now my second date. I met another guy online with the following stats: Irish-American, 6'3", slim, single, no kids, with a Master's, Catholic, lives near me, blue eyes and a slight Boston accent. Nice, huh?
The date was for us to go to the San Diego Zoo, on summers they have extended hours and special events. I told him I had a Membership, so I would go in for free, but he would have to take care of his own ticket. We both get there on time and he was taken aback that he had to buy his ticket, apparently he didn't read that part of the message.
I remember there was a special rate if you got there only for the night time events, but not anymore, it's full rate. He was horrified, so we ended up just taking a walk on Balboa Park (which is free!) During the walk we did have a good back and forth conversation and eventually we sat down in one of the benches. That's when the monologue started, I remember the general themes of his monologues: basketball, Catholicism, technology in education, his previous jobs and other miscellaneous things. While we were sitting down he barely looked at me, so I don't think he noticed my glazed look.
Turns out the guy's not working, and the type of job he's looking for has nothing to do with his Master's Degree in Education. And his bosses are all awful and he gets fired because they are vindictive and/or moody. He has no idea what he wants to do with his life at this point and is looking for a job that can pay at least $15 an hour or start a PhD on something.
Finally I told him I had to go, we walked back to the zoo parking, we arrived at my car first, I slowed down my pace and stopped by my car, he continued walking without slowing down or stopping, only waved good-bye and shouted over his shoulder that I should call him if I wanted to hang out.
Re-cap: too many things wrong here....Next!