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We normally assume that Rabbi Akiva had a most positive world view, as indicated by the famous גמרא at the end of מסכת ֲ מכות, where we find find him laughing even when when he sees (together with the other תנאים) foxes coming out of the holiest place in the world.(Although that source is the most quoted, there are numerous other גמרות as well, where we find Rabbi Akiva laughing in the face of great adversity.)
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On the other hand, there is a פסוק ֲ towards the beginning of the פרשה which doesn't initially sound so negative, which brought Rabbi Akiva to tears. On the פסוק that says "אישה הפרם והשם יסלח לה", the גמרא (קידושין דף פ"א) tells us ֲ באישה שהפר לה בעלה והיא לא ידעה הכתוב מדבר. וכשהיה רבי עקיבא מגיע לפסוק זה היה בוכה. אמר, ומה מי שהתכוין לאכול בשר חזיר ועלה בידו בשר טלה צריך כפרה וסליחה, המתכוין לבשר חזיר ועלה בידו בשר חזיר על אחת כמה וכמה. Here, the great optimist is for some reason greatly depressed. ֲ 
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How do we resolve the apparent contradiction in Rabbi Akiva's approach? ֲ 
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It would seem that the distinction is the following. When there are events that are beyond our control, then certainly Rabbi Akiva would tell us to look for the silver lining to the cloud, as dark as the cloud might appear to be. After all, Rabbi Akiva was a student of נחום איש גמזו and would always says כל מאי דעביד רחמנא לטב עביד. Even if we can't understand how the event is for our benefit, we trust that the All-Merciful G-d is operating for our good. ֲ  On the other hand, with regards to issues that relate to ֲ our בחירה (which is the topic in our פרשה), Rabbi Akiva had a more somber attitude. There he felt that the responsibility that we have to choose between right and wrong cannot be taken lightly, and sins are in fact a reason for sorrow (if one does not properly repent).After all, we are taught that הכל בידי שמים חוץ מיראת שמים - we cannot "blame" G-d for our failings. We need to recognize the great consequences of our deeds. When a person doesn't live up to proper standards, there is room for grief.
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The need to be careful in areas of human choice is one that has particular significance this time of the year when we contemplate the tragedies that befell our people . We all recall the פסוק from משלי פרק כ"ח that opens the discussion to the אגדות החורבן ֲ in the דף נ"ה גמרא גיטין. The פסוק says אשרי אדם מפחד תמיד, ומקשה לבו יפול ברעה. One is meant to constantly contemplate the potential consequences of his actions. One that does not do so, (as in fact was the case with the various individuals mentioned in those אגדות) , can potentially bring a חורבן.
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In the spirit of Rabbi Akiva's optimism, we should add the following note. Rabbi Akiva teaches us in מכות דף ה that מרובה מידה טובה ממידת פורענות- ֲ the degree of reward for good deeds is that much greater than the degree of punishment for evil deeds. This being the case, we can say that if lack of care and concern of our actions can bring harm and destruction, then certainly our acting out of foresight and thoughtfulness can bring us that much closer to the long awaited redemption.ג€‹