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If one feels like G-d has refused his prayer, has He slammed the door permanently shut on the prayer, or should one keep praying for the same thing?

For example, if one has a female friend with whom he would like to cultivate a romantic relationship, and in spite of his prayers, she wishes to remain a platonic friend, should he keep praying? Would it make a difference if she is already dating someone else?

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    Probably best to pray for a good match and leave the details up to Him. – Double AA Dec 4 '16 at 2:24
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    Welcome to Mi Yodeya David! In general the site is not intended for guidance in particular cases, but for answering general question about Judaism. Therefore, I took the liberty of depersonalizing the question. Feel free to further edit yourself. Consider reading this Beginners' Guide to learn more about the site. – mevaqesh Dec 4 '16 at 3:24
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    Regarding the case at hand, the practical aforementioned suggestion to pray God to facilitate the best match, leaving the details to Him, seems quite reasonable. || Sorry that happier circumstances didn't bring you to the site. Hopefully, you will choose to stick around the site, and post practical wedding related questions in not to long, at the just right time :) – mevaqesh Dec 4 '16 at 3:26
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    See the Talmud Moed Katan 18A mentioned in this answer: judaism.stackexchange.com/a/8125/603 -- There it talks about a person praying to marry a specific girl who was already promised to another (spoiler, it didn't end well) – Menachem Dec 4 '16 at 4:08
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    question, good; example . . . hm – kouty Dec 4 '16 at 4:36
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Quick Answer:

In general you should keep praying. No, the door is never slammed from heaven permanently. However, you should reexamine your prayer and pray for the right things in the situation. You should also back it up with action.

Details:

In general, there is no limit to constructive prayer. G-d always hears you and has mercy. (Here is a story I have heard in Yeshivah.) A woman once asked R' Chaim Kanievsky if she should stop praying for relief of her suffering because she sees no change? He answered that she should continue praying. 1) She may not have earned enough merit yet through the prayers. 2) She may have been decreed to undergo a certain amount of difficult times and the prayer may be speeding things up for her.

However, in the specific case of praying that someone else should feel a certain way, there is a problem. How can you expect that G-d will brainwash someone for you? Lets look at it from another angle. How would you feel if, after you cultivated this romantic relationship with your friend successfully, another woman who you absolutely do not like, would pray that G-d change your mind and make you fall in love with her instead?? What would you think of G-d if he granted that prayer and forcibly changed your mind so that now you dumped your intended girl who you worked for, so you could falsely feel attracted to the other woman?

Here are my humble suggestions on what you should pray for.

1) To know if the romantic relationship you seek is good or bad for you?

2) If it is bad, ask for help to realize you should keep your distance despite the attraction.

3) If it is good, ask for help in recognizing why you are not succeeding in attracting her as well? Specifically, ask that your eyes are opened to the flaws in your character that may be blocking the relationship? Ask for help in knowing how to attract her if she is someone for you.

4) Ask G-d to help you understand your friend's mind and feelings.

5) Tell G-d you are lonely, and it is not good to be alone. Ask him to either grant you this one, or if she is not the one, to grant you someone good for you quickly instead.

Next, you should take the advice of the Mishnah Pirkei Avos Ch 2:4. "..nullify your will in front of G-d's will in order that He should nullify the will of others before your will."

Find something in your service of G-d that you are neglecting. Change your ways and do better. Then, if this girl is for you, but there are just issues blocking the situation, your merits of change, with your prayer, will nullify the opposition.

Finally, you should invest in a book about relationships and self esteem/self-confidence. Investigate how hard it is for some women (and why) to view a friend as a romantic interest. Discover if you are lacking in self esteem or confidence by wanting a specific someone else too much? This shows G-d you are willing to make a practical effort as well as praying for supernatural intervention.

When you pray and also couple your prayer with serious honest and sincere effort in this world too, the combination will bear fruit and happiness.

I hope this helps. :)

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Concerning the "romantical" issue, CYLOR, but you address a very interesting and important topic.

This is one of a main issues in the life of everyone.

From this link:

ולכן צריך אדם להתאמץ מאוד בתפילתו, ולא יחשוב שאם הוא מתפלל חייב הקב"ה למלא את מבוקשו, אלא ימשיך ויתפלל, וידע שהקב"ה שומע את תפילתו, ובודאי ‏ תפילתו פועלת לטובה, אלא שאין אנו יודעים איך וכיצד‏

A man need to make a great effort and not to think that if he pray, Hakadosh Baruch Hu is in duty to agree his requiest, but he need to continue to pray, and to know that Hakadosh Baruch Hu hears his prayer. Surely his Tefila has a good effect, but we don't no how.

You ask:

If one feels like G-d has refused his prayer, has He slammed the door permanently shut on the prayer, or should one keep praying for the same thing?

--> YES Berachot 32b (thanks to @Shmuel Brin)

א"ר חמא בר' חנינא אם ראה אדם שהתפלל ולא נענה יחזור ויתפלל שנאמר (תהלים כז, יד) קוה אל ה' חזק ויאמץ לבך וקוה אל ה'.‏

R' Hama son of R' Hanina said: If a man sees that he prays and is not answered, he should pray again, as it says, Wait for the Lord, be strong and let thy heart take courage; yea, wait thou for the Lord.

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