"Tip # 4. Don't help him ask you out by texting him something nice or polite. I'm glad you're more outgoing and thoughtful than he is, but he doesn't want the help."This is a tough one, but I'm going to tell it like it is. My sister once said she was tired of teaching her boyfriends how to be boyfriends. As a guy, I will tell you that we could use all the help we can get, but you should be careful of preventing him from growing and learning on his own. Trust me, he'll be better for it.
You see, if you didn't nudge him to ask you out, would he have taken the initiative? Could this lead to him never taking the initiative in your relationship? Never plan your dates, surprises, etc? This could be a stretch, but seriously... don't get in the way of the learning process. I'm not saying don't text him back, but let him fail and succeed on his own. If he can't pass the test. He shouldn't be riding your ride. No freebies. It's not that he doesn't want the help. He just shouldn't need it.
"The man will really see no reason to call since you are doing it anyway. While he will be content with the fact that you are already making the calls, you will be burning with frustration as it seem every time you're the one to call him." -- Should Women Take The Initiative to Call The Men?
Tips For GIRLS: How to Text a Guy
(This is part 4 of the "31 Things" series inspired by the article, "Things I Wish I'd Known About Dating When I was 21".)