Men Reflect On Past Romantic Regrets

Are you haunted by regrets about a relationship from your past that didn't work out? Learn how to avoid making those same mistakes with the next woman you fall for by following this expert advice.

By Dave Singleton

n his hit song, "My Way," Frank Sinatra sang, "Regrets? I've had a few, but then again, too few to mention." So does that mean that if you have regrets, you should just act like they don't matter that much? If that's not a typical male response, I don't know what is! The real truth is that, much
Years later, our breakup bothers me. I just don't show it.
like Sinatra himself, most men have had at least a few romantic regrets — and they definitely do matter.

According to a study conducted by researchers at the University of Illinois at Urbana-Champaign and the Kellogg School of Management at Northwestern University published in a recent issue of Social Psychological & Personality Science, while women were more likely than men to have regrets about romantic relationships, men had their fair share as well. About 44 percent of the regrets described by women were about relationship mistakes, compared to 19 percent for men.

Despite that obvious gender difference in the study's results, it's a mistake to dismiss a man's pain when it comes to love gone wrong. "In my practice, men who cared deeply for the women they lost are just as regretful, if not more so, than women," says Randi Gunther, Ph.D., psychologist and author of Relationship Saboteurs: Overcoming the Ten Behaviors that Undermine Love. "I believe it has to do more with a person's commitment to self-accountability and how much he or she really knew the person lost. In general, our society doesn't ask men to be as accountable as [what] they demand from women, but that is only in relationships. In battle, sports, politics, religion and business, guys had better take the hit if they deserve it."

To find out more about men and their love-life regrets, I asked several of them to share their biggest disappointments with me. These are their stories, along with tips from experts on how truly wise guys can learn from their experiences in order to avoid making those same mistakes in the future.

"Years later, our breakup bothers me. I just don't show it"
"When my girlfriend Marie and I hit a rough spot after a couple of years, she wanted to work on the relationship," says Bostonian Greg, 38. "I freaked out, but didn't show it. A wall went up and stayed up, and she assumed it was because I didn't care. I cared. Emotional stuff makes me shut down, and I regret I didn't respond or fight harder to stay together. Years later, our breakup bothers me. I just don't show it."

Tip: Understand the role that cultural conditioning plays a role in how men express their regrets, and that it's OK to share how you feel. In fact, it might help your healing process.

"In our society, men are 'programmed' to be less tied to their emotions — movies, TV, and the popular media perpetuate a strong, decisive, unemotional live-and-let-die male stereotype," says Marc Muchnick, Ph.D., author of No More Regrets! 30 Ways to Greater Happiness and Meaning in Your Life. "The implication here for men is that when relationships don't work out, suck it up and move on. For women, the expression of emotion — in this case, the feeling of regret — may come more naturally and be less socially taboo. The reality is that men too may harbor regret about their relationships, but they just might not let you know about it."

"She was the one who got away"
"I work with a beautiful woman and had a huge crush on her," says Marylander Mark, 30. "She was right next to me every day and I never asked her out. We had the best times just hanging out at the office.
Guys tend to regret not taking a chance to see what could have been.
There was a real connection. But a year ago, she started dating a guy and is madly in love with him. I feel like I blew my chance. She was the one who got away."

Tip: The study found that men tended to more keenly regret what they didn't do rather than the mistakes they thought they'd made in regards to their love lives. Since it's the road not taken that preys on your mind, carpe diem — seize romantic opportunities as they arise!

"Guys tend to regret not taking a chance to see what could have been, especially if we did something to screw it up," says Dr. Ish Major, psychiatrist and author of Little White Whys: A Woman's Guide through the Lies Men Tell and Why. "Men definitely regret all the things [left] undone and words unsaid. Sugar Ray's song, 'When It's Over' is such a guy anthem, and it captures this sentiment perfectly."

"I should have tried harder to make things work"
"I took my first long-term girlfriend for granted," admits Virginian Mike, 41. "We were together six years and lived together, but I was preoccupied with school, work, and my own life. I miss her, and I should have tried harder in our relationship. I didn't do enough to make her feel special and to focus on creating a life together."

Tip: Experts agree that it's best to go into a new romance knowing you have to work at it if you want it to survive. "You have to keep the spark alive — maintaining a relationship takes creativity, effort and spontaneity," says Muchnick.

"The most important thing is to keep a relationship from dying," says Gunther. "After-the-fact solutions or regrets are never as good as preventing the breakup if the relationship still has good stuff in it. Partners who care enough about each other and have the tools are not surprised when a relationship is dying. Only those who aren't paying attention are caught off-guard."

"I was overly possessive"
Ruminating on a relationship of his that went belly up a few years ago, "I was overly possessive of my girlfriend's time," says Stephen, a 35-year-old Georgia native. "I wanted her to be 'on call' for me when I wanted to hang out. I was dismissive of her friends and angry when she wanted her girls' night out. I understand now why she bolted for the door. But I'm learning how to take a step back, get into my own life and friends more, and not be so jealous anymore. This time around, I have a girlfriend who is patiently helping me understand that it's not fair to her, and that it has a negative implication on us when I cramp her style."

Tip: Use your regrets as motivation to do things differently the next time you're with someone. "You're so ahead of the game if you can learn from the past and not make the same mistake twice," says Muchnick.

Bottom line: A healthy amount of regret is a good thing, because it can motivate you to get things right when the chance presents itself with someone new. In the end, all men make romantic mistakes — but it's how you get up and rebound from them that matters most. Instead of letting regret dominate your thoughts, give yourself credit for what you've done right and focus on not repeating those patterns from past relationships that didn't work out in the future.

To learn how women approach their own romantic regrets, read 5 Women's Regrets About Former Flames.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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