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5 Tips for Avoiding Regrets About Love

Study of 700 people uncovered key advice for avoiding relationship regrets.

Source: g-stockstudio/Shutterstock

Regrets about love are ubiquitous in literature, theater, and music. (Consider almost every country song you have ever heard.)

But very little practical guidance has been written about how to avoid having relationship regrets. In my interviews with 700 older people—who had vast experience both in and out of relationships—I was keenly interested in what they would say younger people could do to avoid regretting their actions when it comes to love, relationships, and marriage. I was not disappointed—they provided useful guidance on how we can improve our chances of regretting nothing in our lifetime search for love.

Here are five rules from the oldest (and wisest) Americans:

1. Pay Attention to Your Intuition 

In choosing their partners, nearly all of the elders described a powerful sense of rightness, an intuitive, overwhelming conviction that you have made the right choice. Call it what you will—spark, intuition, gut feeling—they agree that you shouldn’t commit to a relationship without it. But in even stronger terms they warn about the flip-side of the in-love feeling: Never get married without it—or you could be in for major regrets.

Because for regret prevention, even more important than the “in-love” feeling is the opposite: Let’s call it the “this is wrong” feeling. Many described this feeling in remarkably similar terms—a visceral, intuitive, nagging sense that the relationship is just not right. It may be so faint that you have to search your feelings carefully for it. But the elders report from their own—sometimes tragic—experience that you ignore the warning of that feeling at your great peril.

A vivid and poignant example of this hard lesson came from Kathy Andrews, 78. She was married to Ben for 20 years until she finally got up the courage to divorce him. They met while they were undergraduates at college. Early on, she told me, there were red flags that should have warned her away from the relationship. But her boyfriend was extremely persistent and her friends were encouraging. She fell into the engagement and did not have the will to break it off.

Looking back, she talked about the absence of the “in love” feeling:

There was one warning I should have paid attention to, and I hope younger people will listen to this carefully. Here’s the thing: I sort of had a sick feeling somewhere down there. A gut feeling that at some level, I knew that I wasn’t really in love with him and that this was a mistake. It was a warning sign. But I wasn’t wise enough to realize it at the time. I just kind of shut my mind to it.

There was a ritual in our college. It was well-intentioned and supposed to be how your fellow students would share your joy. When a guy got engaged, a bunch of other men would dump them in a lake on campus. For girls it was different; they dragged them into the pool and doused them in there. Of course many girls looked forward to this; they were proud to have a future husband and I suppose they liked the fact that others might envy them. I knew I should be happy and excited. But when they came to me for the dousing, I noticed a sinking feeling in my stomach. I was—this wasn’t quite right. It’s a feeling that’s hard to describe. It was a feeling like, “I don’t think so…”

If only I had listened to that feeling!

The marriage was disastrous and ended in divorce. Kathy’s message is that you probably know on some level if the relationship is just plain wrong, but it requires listening carefully to the inner voice. You need to follow the warning of the “this is wrong” feeling, even if there is social pressure to stay the course.

2. Conduct Due Diligence

Yes, the elders say that instinct and intuition are important. But the second rule for regret prevention is this: You may be in love, but don’t park your reason at the door

The elders believe you need a systematic process for evaluating a prospective partner. Some of them even used a business metaphor: Conduct “due diligence” on your partner. Lest this seem unromantic, recall that’s exactly what they want you to do: Bracket romantic love in one compartment of your brain. Now take a good look at whether your partner has objective characteristics that make him or her a good life partner.

Now that you’re serious, the questions should move to the forefront of consideration: Is he or she good marriage material? Is he or she likely to be a responsible and committed partner? If your love won’t stand this kind of close scrutiny, they question how deep that love was in the first place.

The elders say there is a set of important and practical issues you should carefully assess before you commit to a relationship. Some may sound old-fashioned, but that’s just what you should do—think in an “old-fashioned” way.

You need to ask the question: Will my partner be a good provider? Most couples need two incomes to achieve their financial goals. As it has been forever, marriage is an economic institution in which most people pool their finances. Your economic success and standard of living will be connected inextricably to that of another person. Therefore, you must consider whether your potential partner is economically viable.

Cecilia Fowler, 76, summed up the problem:

It’s hard to think about material things when you’re physically attracted to someone; it’s hard to put that aside. But one thing to look at is both of your attitudes toward work. If you’re a hard worker and you want to push, push, push, and the other person doesn’t, it’s hard. It’s awfully hard to be working all the time and someone else is sitting there watching you. Imagine what two people could accomplish if both were filled with the same fire and drive. But if one has to be carried all the time, that’s hard. So you should look at the personality of the person. Do they want to succeed in school, or succeed in their work, or succeed period? It’s something you need to take into consideration.

A key step in the due diligence process is therefore a careful observation of the prospective partner’s work habits: Does he bounce from job to job? Is she unable to make career plans, and so plugs away in a dead-end job, without looking toward the future? Or worse, does he or she not even look for work, and instead depend on you for support or ask for loans? The experts argue that such behavior is unlikely to change after marriage—and you may regret it.

3. Make Sure Your Values Align

Americans love the idea that “opposites attract,” when two radically different people overcome their differences and live happily ever after. Movies replay this theme again and again, from My Fair Lady to Pretty Woman to You’ve Got Mail. Because isn’t love all that matters? In answer to that question, the elders say: Nope.

Indeed, among all of the advice about choosing a partner, one particular lesson stands out: You and your partner must share the same core values.

They hold that much of what is good in a long-term marriage comes from having similar values and worldviews, and, conversely, much of what goes wrong results from incompatible value systems. If you want to avoid regrets, the elders say that the most important task a couple must accomplish before making a firm commitment is to answer the question: Do we share the same values regarding the most important things in life?

Warren, 86, put it succinctly:

Most important is understanding the other person’s values to see if they reasonably relate to your own. What do they care about? How do they think about the world? What matters to them?

The elders tell you to think twice (or more) before committing to a relationship with someone who does not share your core values. Personalities can be complementary. Different interests can spice up a relationship. But a clash in basic values is something a marriage cannot easily survive. Three especially important areas to talk about before you marry—values about money, about religion, and about how children should be raised.

4. Look Carefully at Your Partner’s Family

The elders agree: You don’t just marry a person; you marry his or her family. By this they mean that your partner’s relatives will be a lifelong ingredient in the recipe of your married life. Thus, an essential part of avoiding regrets is to take your prospective partner’s family into consideration before committing to marriage.

Most people don’t think about in-laws much while dating. But the elders tell us that once you are married, each partner brings a cast of diverse—and sometimes quirky or difficult—family members to the marriage. If we like them, it’s a bonus. If we don’t, we can be locked in a lifelong struggle to minimize conflicts and accommodate to disappointments.

Cindy, 72, put the fundamental issue this way:

There are big differences between two families that cause you to have to work at it. But everybody’s got them. You know, I figured out a long time ago that the only trouble with in-laws is that they are not you. They don’t have the history you have. That’s what makes your family easier to deal with because you know what to expect. But your in-laws’ biggest sin is they’re not you and they’re not your family.

Scientists agree: Studies of newlyweds find that satisfaction with in-law relationships is strongly correlated with overall marital happiness. On the flip side, marriages in which there are discordant in-law relationships have lower chances of succeeding over the long-term. There’s no question: In-law relationships really matter.

Of course, some couples do overcome in-law problems. But the elders warn you to be wary of a combination of a highly toxic set of future in-laws and a partner who is enmeshed with them. They won’t make your decision for you. But they say failure to take your future in-laws into account when selecting a mate is often a path to regret.

5. Say It Now

One major regret the elders expressed was not things they had said, but rather things they did not say. Some of the saddest comments had to do with the failure to express deep feelings of love, gratitude, or even simple compliments throughout the relationship.

Janice, 83, told me:

Well, we of course are quite old now, and when we were young it was common for people not to be demonstrative. So neither I nor my husband was very much into showing our feelings or our emotions much. That is one thing that I would do differently. I would try to be more affectionate and then I think he would have eventually learned how to be also. I knew that he cared about me and everything, but it was just the small little things that weren’t there, just through everyday life. I really missed that. I could have done something about it, but I did not really realize that at the time. And as the years went by, it was just a pattern that never changed.

So try simply upping the number of small, positive things you say to your partner. According to the elders, it can improve and enliven your marriage—and help you avoid regrets.

I look forward to hearing your suggestions for how to avoid regrets about love, romance, and marriage!