The concept of "contrapasso" in repentance

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I have two imaginary scenarios:

Scenario A: I finished second, third, or even last place in a long jump competition but still had a small tantrum (but not to the extent where Ibragim Samadov threw his bronze medal at the 1992 Summer Olympics) because I experienced being called a loser in previous games in which I didn’t finish first place. Then I felt that I sinned by not accepting defeat graciously.
Self-recommended contrapasso: I shall not attend any athletic or academic competition to avert myself from being called a loser and making a fuss out of sportsmanship.

Scenario B: When attending a disaster-preparedness seminar, instead of focusing on the keynotes, I become instantly fixated on some friend whom I met only on Facebook. I went home empty-minded; now I realized that I attended the seminar only to flirt with a stranger.
Self-recommended contrapasso: I shall never date that woman again (going as far to completely forget her); any further attempts would inevitably result in a broken relationship with her and with my family.

I want to clarify this question: does the concept of repentance require that I “reverse” the sinful actions by obeying the contrapassos stated above, or is it just that every time encounter such occurrences, I resolve to avert the near-occasions embedded within and finish with a “clean” ending?
 
I have two imaginary scenarios:

Scenario A: I finished second, third, or even last place in a long jump competition but still had a small tantrum (but not to the extent where Ibragim Samadov threw his bronze medal at the 1992 Summer Olympics) because I experienced being called a loser in previous games in which I didn’t finish first place. Then I felt that I sinned by not accepting defeat graciously.
Self-recommended contrapasso: I shall not attend any athletic or academic competition to avert myself from being called a loser and making a fuss out of sportsmanship.

Scenario B: When attending a disaster-preparedness seminar, instead of focusing on the keynotes, I become instantly fixated on some friend whom I met only on Facebook. I went home empty-minded; now I realized that I attended the seminar only to flirt with a stranger.
Self-recommended contrapasso: I shall never date that woman again (going as far to completely forget her); any further attempts would inevitably result in a broken relationship with her and with my family.

I want to clarify this question: does the concept of repentance require that I “reverse” the sinful actions by obeying the contrapassos stated above, or is it just that every time encounter such occurrences, I resolve to avert the near-occasions embedded within and finish with a “clean” ending?
While we are to avoid the near occasion of sin–an alcoholic should not be frequenting bars, for example, or we should not be sneaking peeks at pornography, we are not to avoid life with all of it’s risk of temptation and sin. That is impossible to do, and also there appears a very real danger of scrupulosity developing here.

We are not required to make up our own “punishments” for sin, which is what the above suggests. You can’t “reverse” a sinful action–once a deed is done,it is done. The priest gives us a penance, and we should fulfill that without adding unnecessary burdens to ourselves. We have been absolved and Jesus has forgiven us, we intend to avoid sin in the future, but adding such things to this betrays our lack of trust in the absolution and forgiveness of Christ. God’s forgiveness and love are unconditional, it does not require such actions other than the ordinary avoidance of things which put us in danger of sin.

I would suggest, instead, that you focus on praying for strength to avoid temptation, rather than remove yourself from the ordinary actions of life as a self-styled punishment for your sin (I am not sure the two examples you have given are even sins–that seems to be a stretch). I also suggest you find a spiritual director to help you find a balanced approach to this. I think you are heading down a rather slippery slope.
 
Okay, I understand; I’m just going to take the clean paths and pray a lot.
 
mkdl_v17;9636224 [QUOTE said:
]I have two imaginary scenarios:
Scenario A: I finished second, third, or even last place in a long jump competition but still had a small tantrum (but not to the extent where Ibragim Samadov threw his bronze medal at the 1992 Summer Olympics) because I experienced being called a loser in previous games in which I didn’t finish first place. Then I felt that I sinned by not accepting defeat graciously.
Self-recommended contrapasso: I shall not attend any athletic or academic competition to avert myself from being called a loser and making a fuss out of sportsmanship.
If it is a moral failure to be disappointed at losing a race, it is a moral failure to be happy and celebrate winning.

I a person has a problem with being a gracious loser in an athletic competition the same tendency will come out in other life situations.

The person should enter competitions knowing about the tendency to be a poor loser and learn to overcome the fault by willing himself to be gracious and cheer the winner,
Scenario B: When attending a disaster-preparedness seminar, instead of focusing on the keynotes, I become instantly fixated on some friend whom I met only on Facebook. I went home empty-minded; now I realized that I attended the seminar only to flirt with a stranger.
Self-recommended contrapasso: I shall never date that woman again (going as far to completely forget her); any further attempts would inevitably result in a broken relationship with her and with my family.
There is nothing sinful in being attracted to a potential spouse and being distracted from a seminar or lecture subject matter by her, or going to the event for the sole purpose of being in her company.
I want to clarify this question: does the concept of repentance require that I “reverse” the sinful actions by obeying the contrapassos stated above, or is it just that every time encounter such occurrences, I resolve to avert the near-occasions embedded within and finish with a “clean” ending?
You are required to do the penance your confessor orders and believe in faith his words to go in peace, God forgives your sins.

This is why we need help in dealing with sinfulness. People get confused and need guidance. You should not be self-recommending remedies to your faults. In one case it is not even a fault that needs a remedy. If you do, judging by the scenarios and responses you posted, you are going to tie yourself in knots and drive yourself crazy.
 
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