Was Achsah's request too bold?

You do not have, because you do not ask. (James 4:2b)

So if you who are evil know how to give good gifts to your children, how much more will your Father in heaven give the Holy Spirit to those who ask Him! (Luke 11:13)

The second scripture above from Luke is a story Jesus delivered just after teaching the disciples 'The Lord's Prayer', in the section on how to pray.

We know of the more familiar examples of Bible people asking things boldly. David, Jeremiah Habakkuk, Job, Hannah...they all asked for things of the Lord and did so honestly, with raw intensity. There is no doubt that they were sincere believers who felt awe and reverence for God. They feared Him. Yet when it came time to pour out their heart in naked emotion or bold prayer requests, they did.

Here is a less well known example of someone in the Bible asking for something of her (earthly) father, boldly. Achsah. Here she is in scripture, Judges 1:12-15,

And Caleb said, "He who attacks Kiriath-sepher and captures it, I will give him Achsah my daughter for a wife." 13And Othniel the son of Kenaz, Caleb’s younger brother, captured it. And he gave him Achsah his daughter for a wife. 14When she came to him, she urged him to ask her father for a field. And she dismounted from her donkey, and Caleb said to her, "What do you want?" 15She said to him, "Give me a blessing. Since you have set me in the land of the Negeb, give me also springs of water." And Caleb gave her the upper springs and the lower springs.

Was Achsah too bold? Was she greedy? Was she rebellious in her asking when she should have remained meek and submissive? The Jamieson Fausset Commentary explains it this way

that is, when about to remove from her father's to her husband’s house. She suddenly alighted from her travelling equipage—a mark of respect to her father, and a sign of making some request. She had urged Othniel to broach the matter, but he not wishing to do what appeared like evincing a grasping disposition, she resolved herself to speak out. Taking advantage of the parting scene when a parent's heart was likely to be tender, she begged (as her marriage portion consisted of a field which, having a southern exposure, was comparatively an arid and barren waste) he would add the adjoining one, which abounded in excellent springs. The request being reasonable, it was granted; and the story conveys this important lesson in religion, that if earthly parents are ready to bestow on their children that which is good, much more will our heavenly Father give every necessary blessing to them who ask Him.

The last sentence of the commentary explanation harks back tot he verse from Luke above. And here is another short explanation of this small incident from Judges about Achsah, it is Matthew Henry from his Complete Commentary. The tenth commandment was "Do Not Covet."

From this story we learn, 

1. That it is no breach of the tenth commandment moderately to desire those comforts and conveniences of this life which we see attainable in a fair and regular way. 

2. That husbands and wives should mutually advise, and jointly agree, about that which is for the common good of their family; and much more should they concur in asking of their heavenly Father the best blessings, those of the upper springs.

3. That parents must never think that lost which is bestowed upon their children for their real advantage, but must be free in giving them portions as well as maintenance, especially when they are dutiful. Caleb had sons (1 Chr. 4:15), and yet gave thus liberally to his daughter.

Ye have not because ye ask not! Now, just because we ask, doesn't mean we will get what we ask. God is not a magic genie, bestowing upon us all that we desire. There are conditions to asking boldly of our Father in prayer. First, the rest of the James verse explains that sometimes we do not receive because we ask wrongly. If we are asking in order to indulge our passions, it will not be granted. If we regard iniquity in our heart, prayer will not be heard. (Psalm 66:18). There are other conditions, too, which if in place mean the prayer will not be heard, no matter how bold it is. (source with scriptures here,please look at the list).
Conclusion:

Prayer: Nothing is too great and nothing is too small to commit into the hands of the Lord!

-- A. W. Pink

Our Father who is holy, will give good gifts. Be bold in prayer, be diligent in asking, be sure of the result.

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Further resources:

Sermon "Pray Boldly", here John MacArthur explains the weird scene from Luke 11
jmac sermon "don't be afraid to ask'

Charles Spurgeon's sermon Have not because ye ask not? exposits the scene with Achsah.

Thomas Watson quotes on prayer, here at Grace Gems

Valley of Vision, The Prayer of Love