On the younger years regret seems one of the most aweful thing that could happen to you. Through the teen and young adult years we tend to pack a lot on regret and measure most of our steps - past, present and future - against regret. Then, as you get older you realize that regret doesn't need to be such a terrible thing, as long as you live a consistent life and remain true to yourself. Regret is the brand we get on ourselves when we do something we shouldn't have, by our own standards. At least that's what regret should be.
It happens however, that we feed ourselves with measures that are not ours, that do not belong into our personal believes, and feel regret for things we ought not to. Regret for wearing the wrong clothes for a meeting or a party, regret for eating more calories that "you should have", regret for accepting an invitation or a gift, regret for talking to the "wrong people" and such. Even the regret for having friends your social group don't accept, or having taken a job or a class that others don't approve.
Other types of regret are harder to get around of, harder to unwind and even decide whether they belong to our believes or not. In here sometimes people use sayings such as "better to regret what you've done than what you never did", but each case is different. That's why there's better judgment. You may regret more having taken drugs than passing on the chance, but then you may regret not having kissed that person because whatever reason you had not to do it.
Life is full with stories about times when you risk and lose, when you risk and win, or when you risk and live something unexpected. You may be tempted to do something you know that might not be right, that may backfire, but yet you do, and that's okay, as long as you are willing to shoulder the consequences. My life has a lot of moments, beautiful moments where I risked, I went beyond the point where others would, and I've got beautiful, wonderful memories that could never be experienced otherwise. I dared to have one night stands, and gave a fuck about what others would think of me, knowing that the only thing that matters is what I think of myself, after all you can be at Starbucks, seeping on your coffee, blogging, in your generic jeans and a generic polo, hair pulled up in a ponytail and there will be people calling you a whore, a lesbian, a golddigger, a man eater, a frigid bitch, a witch and a thousand things more. Yes, you need to do nothing to have people talking about you, and half of what they say is false, but nobody cares.
Then there are things you do, things you could do, you may risk to do, but come with a burden. Remain forever silent about the matter, or face the consequences of coming clean with the truth and let the present come down to pieces. Think of the case when you get tired of your job or your relationship and you are before a big question: leave and be free but alone/unemployed, or stay and continue enduring hell. The fear of regret is there. And add pressure: a promise of a better job that may or may not come through, or a new relationship that may or may not come through.
Sometimes it worths to risk, sometimes it worths not to do it, but in neither case is regret what we should fear, but the possible consequences, and decide if we can really live with them.