When should I ask again?

I asked a girl out on a dating website. We went to meet at a coney island but there were five on the road. We decided to meet instead at the movie theater and there was a giant glowing red steakhouse sign and we ate there before the movie. We ate and she told me about herself (which was actually interesting). After I paid for the check with my ninja fast credit card waiter skills we headed over to watch the movie. We were going to see paranormal activity but she wanted to see a horse movie which I agreed to and once again ninja paid for. The horse movie surprisingly enough wasn't bad even thought it was rated pg.

After the movie I told her how much fun I had and asked her if she wanted to go on another date. She kind of agreed but we didn't make any plans. I insisted I walk her to her car (I couldn't allow her to walk herself it was at 11 pm in the night and we weren't too far from Detroit.) In any case when I had made sure she was safely at her car I turned around and was going back to my own car when she asked, "Aren't you at least going to give me a hug." My friends all say she was really asking for a kiss and that I'm a moron. I gave her the hug and we promised to text each other to make sure that we both got home safe. We both did. I texted her again later in the week trying to set something up. She was busy this week. I tried again on Friday but she has parties to go to all weekend.

When should I ask again? I tend to do it too early or late.

It's not looking great for you, to be honest. But you should call her on Tuesday or Wednesday to ask her on a date for the weekend. Most people's weekends aren't completely booked up that early in the week. If she says no and doesn't suggest another time when she's available, then she's not into you and most likely doesn't want to date you.

Darn I thought so :(.

Pssh. Don't let some asshole on the internet discourage you from asking her out once more. Don't give up yet.

Well, If I were you I would not have paid twice. Because now you just prove that you are extremely interested on her which is wrong to show that feeling to her at the beginning. If you didn't pay for her, she would be more interested on you and girl wants someone strong and considers her as not big deal since you don't know her very well at the beginning. I know you were happy with her and interested but don't offer everything by yourself cause you would feel sorry if she is not interested in the future.

Oh I see, I was just trying to be polite. I was raised with an old school kind of view of dating.

Paying doesn't show you're ueber-interested. Especially if you met the girl on a dating site. Your intentions are already somewhat clear, so paying just shows good manners in my opinion. Also, this weekend was halloween. A lot of people had plans. Maybe next weekend will be better.

I told her happy Halloween today and she replied, "you too." So I'd say all hope isn't lost :P.

well if you've tried too times . . .then it's time to move on

. . .mind you, reading that post, it seems liked you paid for lots - save your money and use it wisely.

mate, i reckon you should just stop calling her and wait for her to call you. if she calls you back then sweet as! if she doesnt then she missed out. you tried 2-3's already. stop putting yourself out there too much.