I need to send applications to potential dates....

So I have a knack for attracting some of the weirdest people you could ever imagine dating. This has happened throughout my entire dating history - trust when I say I have some good stories. It would be hard to back track on here because they've just piled up in the 10 years since my dating life has begun. Obviously I haven't been very successful, but it makes for some very interesting stories to tell. :)
So I went out on a date last night with this guy who I met online like a year or so ago. Figured, heck just broke up with the BF not that long ago, why not. Met up for some drinks, had a good time. He was definitly a trip, very energitic, and just seemed like a really interesting person. Needless to say, went well, had plans to do it again.
He texted me not long after to ask if I was "feeling" it, cause he coudln't tell.
Me: "Yeah, I had a good time, I'm just sorta shy until I get comfortable around you, but we can definitly hang out again sometime."
Him: "You should come over to my house to watch a movie."
Me: " No, I'm tired, and I'm not going to jump into bed with you. If you want it, you gotta earn it."
Him: "Earn it? Really? We're adults, you can make that decision for yourself, don't be ashamed. I know you want to."
Me: "If I slept with every swinging dick that looked my way, what would that make me? Sorry, but no. If you wanna do that, you gotta actually prove yourself."

So the conversation continued and got sorta weird. He started asking me a zillion and a half questions.
Him: "Do you like to give or receive?" "Are you a great kisser? Rate yourself 1-10." "What's something you could beat me at?" "What's your bra size?" "What's the best part about sex?" "What's something you stink at?"...
And the list goes on and on and on. And the questions just got weirder and weirder, and very sexual. And continued to ask me to send him a picture of me naked (Really? I'm going to send a naked picture??? Come on dude, I'm not some nieve little girl who believes if I do this you're going to sweep me off my feet on your white horse)

Then he decides it is show and tell time. And he sends me a picture of his penis. Yep, right there, erect and upright. Right on my telephone screen.
Him: "Do you like?"
Me: "Ummm.....I think I'm in shock....."

Needless to say I say goodnight...and the questions just kept coming in.

This morning I wake up to the barrage of texts and then a text to tell me that he emailed me questions as well. I again told him that he was definitly a trip, and I had never had someone text me questions, email me questions and randomly send me a picture of his penis.
Him: "I'm spontanous like that...you have to live with no regrets and just do it. By the way, I emailed you questions, I figured it'd be quicker than texting."

Emailed questions:

What are the best and worst parts of you in a relationship?
Tell me something that would suprise me about you?
Who would win a fight between an apple and a grilled cheese sandwich? Why?
Have you ever made the first move to kiss someone for the first time?

So red flags are now up all over the place, and I have no idea what to do about the penis man.

Yep, a day in the life of Stephanie..... if you think it can't happen, it does to me.