4 Reasons You Should Date a Failure

 By Nina Atwood

Couple hearts question marksFourteen years ago when I met my husband, we were both failures. Relationship failures, that is. He was divorced twice and so was I. We were in our early forties, fearful of making another mistake, yet still hopeful that maybe this relationship would be the right one. We both had a healthy dose of skepticism, but we forged ahead. Good thing we did because meeting him has definitely turned out to be the best thing that has ever happened to me!

If you are single and over forty, odds are you have at least one big relationship failure in your life. Singles often ask me about the people they are dating and whether or not they are worth the risk. He’s been divorced and single for ten years. Is he ready? She’s never been married but lived with a guy for fifteen years. Does she have a problem with commitment?

The twice divorced person may look like a long shot, but it turns out that there are some real advantages to dating relationship failures. If they meet these four criteria, it’s probably worth it to find out more and possibly, to take the risk of falling in love.

One: Healthy Paranoia

Anna is 41, in medical sales, and recently divorced. Her green eyes sparkle as she relates to me the enchanting story of meeting Doug through an online dating service. After one coffee date and one dinner date, she is wowed. “He’s the guy I’ve been looking for,” she gushes. She can hardly wait to introduce him to her family and friends. In her mind, she’s practically engaged to the guy, yet she knows almost nothing about him.

“When was his last serious relationship, and how did it end?” I query. She looks at me blankly. “Well, I know he was married a long time ago, and he’s been single a long time,” she trails off, frowning. She then takes up the narrative of how wonderful he is. I now know she is in deep trouble, overpowered by the temptation to rush in to this new relationship.

The person who has failed and learned from it is smart enough to have a good dose of skepticism about relationships. It’s easy and tempting to fall for the first attractive person who gives you attention. It is much harder to hold back a little until you really understand the person sitting across from you.

Maybe you are skeptical, but do you look for that in others? It might pay to do so. Studies show that the longer you date before becoming engaged, the better your odds are of making a good match, especially if you are focused on making sure your values align.

A little bit of worry about making another mistake helps you pay attention to the warning signs of a relationship that isn’t going to be good for you. If the person you’re dating is also a bit worried about making a mistake, together you are more likely to ask good questions, discuss your values and life goals in depth, and look for real alignment.

Two: Ego Correction

Have you ever asked someone about their past relationships and gotten a diatribe about how crazy and/or evil their Ex was? It’s a huge turn off, for a good reason. Bitterness and finger-pointing are signs that learning has not taken place. Some people never make the crucial step post breakup of recognizing that they were party to the mistakes that were made.

People who have failed in relationships and recognize their role in it are more humble. Rather than putting on an egotistic façade they tend to be authentic, preferring to disclose their baggage instead of hiding it. When you meet someone new, listen for the telltale signs of learning and growth. I had a role in my marriage not working out. I was just as much to blame as he was. I learned a lot about myself and I think I will be a better mate to someone new as a result.

Life and love are challenging journeys. Do you want to go on that journey with someone who can’t acknowledge failure, who is always right and never wrong, and who is never introspective? Or with someone who can, and does, learn from past mistakes?

Three: Curiosity

Before I met my husband, I had dates with men who weren’t the least bit curious about my past history. Instead of asking questions, they talked about themselves, their work, and personal interests. Conversation stayed on the surface. This exposed a huge gap.

With two divorces in my past, I knew I had a LOT to learn, even though I was an educator in the field of personal relationships. It’s one thing to write about love and to counsel others, it’s another thing to be suddenly divorced for the second time and have to figure out what went wrong. It’s grueling inside-out work, but one thing I eventually learned was that curiosity pays huge dividends.

The more questions I asked, the more I saw what I was getting into before I put my heart on the line. I learned to be fearless in my quest to learn more. I consciously looked for a man who would also be curious about the “inside job” of becoming a better mate. When my husband, on our third date, asked me about my role in the failure of my two marriages I knew I had met someone who could learn and grow with me.

If you tend to ask few questions on your dates, you are probably making costly mistakes. Fear of offending someone may keep you silent, but assumptions pile up. The gap in information leads to poor decision making. Learn to push the boundary of what you think is socially acceptable. Question fearlessly, and be ready to answer with your own story of learning. Drop your ego, open up, be authentic, and watch the quality of your relationships zoom up.

Four: Pessimism

People who fail and learn understand the power of looking ahead and planning, with a bit of pessimism. If you assume that finding someone new to love solves all of your life problems, that everything’s rosy and all you have to do is open your heart, you may be setting yourself up for another failure.

I was sitting in one of my favorite restaurants when the owner (whom I had chatted with many times) stopped at the table to share about his upcoming marriage. He’d met his soon-to-be wife just three months earlier, and was madly in love. They were both in their forties with children from previous marriages, so theirs would be a complicated union. But he was 100% positive that this was the most amazing relationship ever! There were no clouds on the horizon. Whoops, I thought. This is not going to be pretty.

Six months later, same restaurant, same guy, but now he looked absolutely beaten down. Within one month of their five star wedding, trouble blossomed. I won’t get into all the gory details, but the net of the story is that their marriage turned out to be incredibly short, and the battle through divorce court long and ugly.

If you want a real chance at happiness the second (or third, or fourth) time around, inject a little pessimism in your plans. Talk about what would happen if . . . (you didn’t agree about money, your step kids didn’t get along with each other or with you, you felt insecure, one of you lost your job, your sex life began to wane). Talk about the built-in issues and emotional baggage you each bring to the relationship.

The conversations you have about these issues enable you to emotionally prepare for the inevitable road bumps. You also get the opportunity to preview one another’s style of conflict resolution.

Failures That Are Worth It

The old saying is that what doesn’t kill you makes you stronger. Relationship failures really understand that. My husband and I are better partners for the mistakes we’ve made in the past. We are deeply grateful that we gave one another the chance. With healthy paranoia, ego correction, curiosity, and a small dose of pessimism, we’ve made it thirteen years and love each other more than ever. Cultivate these qualities in yourself, look for them in your dates, and the failures you’ve had in the past may just turn out to be your best asset.

Entry Filed under: Advice for Men,Advice for Women,Dating,Divorce,Marriage,Relationships


  • 1. Julie  |  April 10th, 2013 at 9:41 am

    Thanks for the perfectly timed blog Nina! I commented on your getting through the holidays blog nd at that time things were not going well at all! I had decided to put dating on a back burner because I was dealing with some depression and a job I hated. Well, it turns out part of my depression was caused by medical issues. I had surgery and started to feel better until returning to work. The depression and anxiety were back full force after 2 days back at my job ( in a public aid office). So, I prayed hard for several weeks and decided to give notice. I have been focusing on my friendships and trying to get out more socially. Well, a few weeks ago I joined an online dating site not really expecting anything other than to get back out there. I talked to several seemingly nice men and one I seemed to hit it off with. We had a date Saturday night. We had dinner and watched a band for a bit. I kept things fairly short but probably not as short as I should have. There was definite chemistry but no hand holding or kissing. He texted me the next day and has consistently every day since. If I had to describe all the qualities I’m looking for he seems to enbody all of them. We have similiar values. We have so many common interests it’s crazy and we share the same sense of humor. My problem is I am so afraid of rushing in and screwing this up. I’ve read your books and know I should probably be seeing more than one guy but I haven’t talked to anyone remotely as interesting. How in the heck do I calm myself down?? I’m trying like crazy not to imagine the wedding with this guy I don’t even really know. Any advice would be appreciated 🙂

  • 2. Emily  |  April 20th, 2013 at 2:16 pm

    Such great advice! I agree with you that you learn important things through “failures”. What you want and what you don’t want… what’s important to you and what’s not… I think you have some great points. Especially later in life – you can’t expect many people to have a “clean” track record. I know after my divorce I made a conscious effort to be a better partner, and my now-husband is very happy about that! Thank you for the info!

  • 3. Nina Atwood  |  April 23rd, 2013 at 2:56 pm

    Emily: thanks for your comment!

  • 4. Nina Atwood  |  April 23rd, 2013 at 3:00 pm

    Julie: you are smack in the middle of the temptation to rush into a new relationship! You see, it wouldn’t be tempting if you weren’t so attracted. But that is precisely when you need to take deep breaths, slow down and TRUST the process of dating and continuing to get to know one another. Keep active with your old friends and activities. Don’t immediately wipe out your calendar for him. Distract yourself with exercise and time with friends. Mediate, journal. Most of all, TRUST yourself to maintain that line of slowly building a strong foundation for real love.


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