Page 2 of 3
When you are trying to break the ice via a text, you want to show her what you are made of. Show her that you have a personality, and are not some other Joe Blow helplessly looking for a date. Throw something witty into the text that will put a smile on her face. For instance, you could send “It's okay. I give you permission to stop dreaming about me now!” While that's not exactly subtle, it does convey that you have confidence and it also has a lighthearted connotation that can help put her at ease. If you add a tad of entertaining value with your texts early on in the game, you will catch her attention and make her want to receive new messages from you. Also, she won't feel burdened by having to answer the usual dull questions that overload her inbox.
Use texting to your advantage here. You can be more daring than you might be over the phone on that dreaded first call. She can't hear you or your possible stuttering and nervousness, so make it good!
Less is more

Texting is just a small fraction of the flirting pie, so don't overdo it. You don't want to text your entire life history. Don't send messages detailing where you grew up, where you went to school, what type of hobbies you enjoy, etc. Instead, use texting to flirt and show her that you are a fun person to be around. Avoid being too serious. This is supposed to be your avenue to give a sneak peek as to what you are about. As mentioned earlier, do not send generic, boring questions. Build some playful rapport. Maybe she's having a stressful day and wants to unwind. If you show that you are humorous and have a good personality, she will look forward to more texts and playful banter. If you're lucky, she might even decide to unwind with you. If you are comically challenged, look up some icebreakers on the internet and add them to your texting repertoire. Google is your friend. Just be sure to avoid one's that are obviously overused and played out.