“I Should Have Had More Sex Before Sticking with One Guy”

Two roads diverged in a yellow wood, And sorry I could not travel both…Yet knowing how one way leads on to another way, I doubted if I should ever come back.” —Robert Frost

“The greatest regret in my life is that I slept with so many strangers. One night stands are always regrettable” —Jane

“The greatest regret of my life is that I should have had more sex before sticking with one guy.” — Janet

Our love lives are full of romantic regrets, ranging from our choices of unsuitable partners to missed opportunities to establish a quality romantic bond. Do such regrets have a functional value and should we pursue them?

There are two main types of regret: regretting an action we took and regretting an action we didn’t take.

In the short term, we tend to regret actions we took in the past, and in the long term, we regret missing opportunities.

It follows, therefore, that in the “morning after,” people often regret casual one-night stands, but when looking back at their lives, they regret missing out on opportunities that could have developed into great love.

There is a major difference between these types of regret: while wrong deeds can be corrected and compensated for, missing opportunities can no longer be fulfilled and so the regret endures for longer.

Romantic regrets are common in almost everyone, but they are more frequent in women and those who are not in relationships.

When women regret, they focus more on personal relationships, while men regret choices they did or didn’t make in their career. That said, gender differences have decreased in our era.

What is the biggest regret in your life?

When women were asked, “What is the biggest regret in your life?”, they vividly regretted actions they mistakenly took and actions they missed:

“I divorced the father of my children.”

“Getting married when I had stronger feelings for someone else.”

“I regret that I got married too early, I divorced too soon, I married an unsuitable man, I did not divorce this man when I wanted to, and most men I dated were unsuitable for me.”

“Getting into a relationship with someone I did not have romantic feelings for because I was lonely and in a difficult place emotionally. I will never do that again.”

“I love my boyfriend and I want to spend the rest of my life with him. However, I regret not dating or sleeping around more before getting into a committed relationship.”

“Staying with a guy who showered once a week and always smelled nasty.”

“Being too shy.”

“Not meeting my lover before.”

“I did not continue a relationship with a man who loved me very much (I was not sexually attracted to him).”

“I only regret that I married my husband when he annoys me.”

“I was with a stingy man for far too long.”

“Chasing after a guy that obviously didn’t want me and didn’t treat me well”

“I had two relationships where I dragged them out even though I knew I wanted out of them; I saw red flags but still tried to make it work.”

“Not being selfish enough; not speaking up for my needs.”

“I did not invest enough effort in finding someone suitable.”

“I was too obedient to my parents and did not continue relationships that I had just started that they didn’t approve of.”

Do we all have regrets?

“Regrets, I had a few, but then again, too few to mention…I did it my way.” —Frank Sinatra

“No, I regret nothing, Not the good that has been given, Not the bad, it’s all the same to me. It is done, forgotten. I don’t care about the past.” —Edith Piaf

“I have no romantic regrets, as I always dated women who were wrong for me.” —Noam

On her 75th birthday, the actress Brigitte Bardot stated that she regretted nothing. This is a common view which we often hear expressed in the claim, “If I could go back and do it all over again, I wouldn’t change a thing.”

Still, although many people boast of their lack of regrets, few of us never experience regrets (Davidai & Gilovich, 2018).

Perhaps those who claim to have never experienced regrets are aware of making mistakes in their lives, but like Frank Sinatra, they accept their imperfect way of making decisions, guided by their heart.

The nature of one’s regret can change over time. Thus, Jonathan, a divorced man in his fifties, insists, “I regret that I did not marry the rich woman who wanted to marry me. I did not love her enough and did not want to marry for money. Today, I believe it was a mistake.”

Love contributes vastly to our happiness and in this sense, Jonathan was right not to marry this woman. However, his regret is based on the possibility of love changing—love can develop or vanish with time. In both cases, money can help.

Incidentally, Jonathan’s regret was enhanced when he heard, a short time after their separation, that the woman he had considered marrying had become sick and died—meaning that, if he had married her, he would have inherited her entire fortune.

The Beatles were right when claiming that money can’t buy love, but money can certainly enhance love or a good life after love has died—as many loves do.

Do regrets have a functional value?

“Never yield to remorse, but at once tell yourself: remorse would simply mean adding to the first act of stupidity a second.” —Friedrich Nietzsche

“Have regrets made me a wiser woman, or lessened the chances of making future mistakes? I wish I could say so. However, I need to practice a bit of self-compassion rather than muddle in shame.” —Omer

“Most of my friends regret divorcing those whom they married at a young age. A relative of mine divorced, remarried, and at the age 70 divorced again and remarried his first wife, who divorced her then partner for him as well.” —Nathan

Regret influences our behavior even before we take action. Most people tend to make choices that decrease risks and consequent regrets.

An example of this might be not marrying your lover after a brief dating period or investing time and effort in exciting, promising opportunity.

However, research on short-term sexual regrets has shown that people who regret casual sex do not necessarily stop having such sex in the following four months.

Regret is valuable for self-knowledge, but its impact on behavior is limited. Studies on happiness indicate that moderate singular life events tend to affect happiness in the short term, but people often adapt to change.

In the case of divorce, satisfaction with life first drops, then rises and stays high. And in the case of marriage, life satisfaction builds up before, and fades out after the wedding. Adaptation is an important feature of well-being.

It seems then that Nietzsche was right when he reduced the value of regret, claiming that you should love your fate with its good and bad consequences.

For Nietzsche, life without regret does not necessarily involve considering the future in the hedonistic manner of eating, drinking and enjoying every moment in case of sudden death.

Rather, he advocates accepting the past as unchangeable, while being happy with one’s lot. Such happiness does not mean passivity and lacking the wish to improve one’s life, but rather continuing developing and improving one’s existing positive circumstances.

Behaving in accordance solely with impulsive, emotional drives can be risky in not taking into account more general considerations. Nevertheless, giving more weight to your heart and much less weight to what others feel and want is optimal in many circumstances. I do not think that we should prevent the natural attitude of regret, but regret should not be a meaningful factor in determining our activities. Although regrets are nearly inevitable, we should avoid chronic regrets that force us to live in the past and not in the present.

These days, lovers face multiple challenges. Not only do they doubt which direction to go in, they also regret the roads not taken.

The abundance of romantic opportunities and the possibility of getting something “better” erode commitment.

Such abundance becomes tyrannical power preventing people from enjoying the present. Hence, it is important to remember what the great philosopher from Chicago, Michael Jordan, said: “You miss 100 percent of the shots you don’t take.”

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