Dating Smart by Evaluating Relationship Risk

If you were to ask me for my best relationship advice, I’d tell you this: dating smart protects your heart. The truth is, however, when it comes to relationships most women rely on their feelings, not their intellect. Throwing caution to the wind, they allow their emotions to rule and ignore reason. Then, when the relationship turns sour, they’re blindsided.

When this happens, I find it helpful to ask this question: “Looking back, knowing what you know now, what are the mistakes you made and what are the red flags that you missed?” This is an important question. If you can’t see the mistakes you made the first time, you’re doomed to repeat them.

Hindsight is important because it allows you to examine your previous relationships and try to pinpoint where they went wrong. Are there areas in which you compromised? Did you move too fast? Is there something you overlooked?

If you’re willing to make an honest assessment, this can be a helpful exercise. Given the benefit of hindsight, you’ll be able to bring clarity to the issues you overlooked. But what if you could reverse this situation and instead of just relying on hindsight, use foresight?

That is the whole purpose of this article—to help you use foresight so you can date smart. You’ll learn how you can set your emotions aside and make wise choices based on observation of character. When you’re able to set your emotions aside it’s easier to examine the reality of a man’s character. You are not looking for Mr. Perfect. He doesn’t exist. You’re looking for an excellent choice. There’s a huge difference between excellence and perfection. Excellence is obtainable. Perfection is a myth.

Don’t Skip the Evaluation Process

Evaluating a man’s character is most fundamental part of dating smart. Maybe you think it’s wrong to examine another person’s behavior. It’s somehow not the Christian thing to do. You may feel like you’re being judgmental. Let me just say this—it’s a must. You’re not judging their eternal destiny. You’re evaluating their character to ensure that they’re trustworthy, honorable and relationship ready. You’re being cautious while you take the time to assess his character and evaluate whether or not he is a good fit for YOU.

Let me say it again. Evaluating a man’s character is not judging.

You’re not judging his worth as a human being. Only God can do that. You’re taking a opportunity to consider relationship suitability from an emotionally detached perspective.

It’s important to do this before you get emotionally involved because

your emotions…

will distort…

your discernment.

Don’t make the mistake of making relationship decisions based on your emotions instead of reality. By the time you notice areas of incompatibility, the discomfort of leaving is often stronger than ending the relationship. You may be tempted to stay longer than you wish. Discontentment becomes familiar. Like quick sand, it’s a slow drown.

Proverbs 12:26 says that a wise woman is cautious in friendship.

Consider this:

  • Banks and mortgage lenders do credit checks to make sure candidates are credit worthy.
  • Employers often require a drug test as part of a new hire process. They’ll also check references to make sure you are a good fit for their organization.
  • If you apply for insurance, your insurer will check your claims history to evaluate the potential risk in order to determine the rates they’ll charge.
  • Even if you do volunteer work, most organizations will do a background check—for a volunteer position.

Credit worthiness. Employment suitability. Risk management. Banks do it. Employers do it. Insurance companies do it. They’ll all check you out. So where did women get the idea that to evaluate character is being judgmental? It’s not judgmental. It’s prudent!

Proverbs 14:15 in The Message Bible says this: The gullible believe anything they’re told; the prudent sift and weigh every word.

You’re trying to discern whether or not a man is a suitable investment for the most valuable asset you own—your heart. Is he capable of a healthy relationship now? Not in the future—with a bit of persuasion and work. But now. Be careful not to fall for potential. Potential is like peanut butter. It’s nutty and sticks to the roof of your mouth.

You’ll also want to consider his maturity. Keep in mind that age does not make a man mature. Character does. That’s why it’s so important not to rush. Gauging character suitability takes a bit of time and intentional consideration.

The Character Factor

Aside from chemistry, personality, and common interests, many women overlook the character factor. Even the term character is often vague. So that’s why you’ll find a list of character traits below to help you consider what you value most.

Character trumps chemistry. Chemistry is awesome, but it often has a short life span. It’s like a forth of July sparkler. It looks magnificent and fun at first, but it quickly snuffs out. If you’ve made a relationship decision based only on chemistry, when it fades, your relationship foundation may crumble. But if you’ve made a decision based on character, your relationship will be secure.

Check out the list below and select five to ten traits that are most important to you. It will help you identify must haves and deal breakers. After you select the top traits that you feel are most important to you personally, the next step is to watch and wait. This is the stage where it is important to be in observation mode. You’re making a list and checking it twice. Remember, you’re not judging. You’re being cautious. You’re watching his actions to look for evidence of the character traits that are important to you for future relationship success.

It’s easy to rush this process and jump in too soon. Resist the urge. Watch for consistency. Reliability of character takes time to evaluate. Everyone displays their best behavior in the beginning. You have to decide if his behavior is the real deal or an impression session. Any guy can put on his game face for awhile, but true character is revealed in times of trouble. When he displays that character trait consistently over a period of time and under the heat of adversity, his character is likely genuine.

Consider His Emotional Maturity

Is he emotionally mature or does he have traumatic issues that are still unresolved? If you get in a relationship before these issues are addressed they’ll hinder your relationship and drain your energy and your emotions as well.

I’m not endorsing intolerance. It’s just important to know whether the baggage he brings into the relationship is something you’re prepared to deal with. Evaluate your concerns from an emotionally detached viewpoint. Can you live with it or do you need to leave it? Don’t be his rescuer or missionary because you want to help him get past his past. That’s the job of a counselor.

When evaluating character you should also consider that most character flaws are magnified over time. Many women think that love will make it easier, but the reality is that character qualities that aggravate and frustrate you now will become a thorn in your marriage or relationship later.

Don’t confuse character with temperament.

Personality traits and temperament are different from character traits. Temperament is dealt while character is developed. In other words, we’re born with a personality and temperament. It’s part of our nature. Like the color of our hair and the color of our eyes are part of our physical nature, we’re all born with temperament traits. On the other hand, character is developed over time by the choices we make. It is strengthened or weakened by the trials we endure. But we choose. It’s not what happens to us in life that determines our character. It’s how we respond to what happens to us that defines our character.

Character is the Foundation for a Successful Relationship

Many women choose a mate based on their personality, chemistry and common interests but fail to evaluate character. Character, however, is one of the main ingredients that will cause your relationship to thrive. When times of adversity come his personality won’t get you through difficulties. His character will.

Joni wanted a man who pursued her and who was direct and forthright. But also high on her priority list was a man who was witty and could banter back-and-forth with her. She admired Jason’s intellect and sense of humor. They spent hours talking, laughing and joking together.

Still, something was off. “We have so much fun together, but something isn’t right,” she said. “I want more, but every time I approach the subject, he freaks out and puts walls up. I don’t want to scare him away. Do you think he’ll ever change?”

Knowing that pursuit was important to Joni, I asked her some direct questions. “How often do you call or text? Who is the one who initiates these communications?”

Joni looked at her phone. The text messages didn’t lie. She was the one who initiated every conversation and date. They’d spent so much time laughing together that she didn’t realize she was the one in pursuit.

That’s when Joni took a step back to look at Jason’s character qualities on paper so she could evaluate the realistic longevity of her relationship. Over the next several weeks she slacked off on her texts to see if he would initiate contact. Sadly, she didn’t hear from him unless she texted or called him first. When she tried to discuss her concerns with Jason he avoided the topic or blew it off. His sense of humor camouflaged his lack of pursuit and initiative.

Joni had to face reality—Jason wasn’t invested in the relationship and wasn’t going to pursue her or take the lead. “It was difficult to walk away because I’d elevated his sense of humor and ignored my desire to be pursued,” said Joni, “but the pain of the same out-weighted the pain of the change. I know I made the right decision. I couldn’t be content in a relationship where I was always the one leading.”

When we let our emotions rule we’ll often make unwise choices in relationships. But when we stand back and assess the relationship from a different perspective before we get emotionally involved, it’s much easier to evaluate the risk. This is a very difficult thing to do after you are emotionally attached. Emotions will skew and distort the reality. Your friends will be able to see the warning signs. But once you are emotionally connected you’ll have to compromise, minimize, or tell yourself lies in order to carry-on.

Examples of character traits to assess:

Does he exhibit self-control?

How does he handle anger and frustration? Does he have addiction issues with drugs, porn, or gambling? If so how long has he been clean? Does he honor your sexual boundaries? Or does he ignore your wishes and violate your boundaries? Is he confident or self-absorbed?

Sometimes self-absorption can camouflage as confidence. It can take time to tell the difference. Here are some questions you can ask yourself. Does he talk about himself all the time? Does he interrupt you? Does he give you time to share your views? Does he ridicule your ideas? Does he talk over you?

Tammy confused her first husband’s arrogance for confidence. “I admired the way he took charge of things,” she said. “He seemed so driven and ambitious. After we got married I became increasingly frustrated that he cared little about my opinion. He was always putting me down and demanding his own way. I should’ve seen it earlier.”

Can you deal with untidiness?

Nick never picked up his things. “That’s just the way I am,” he told Janie. “I’ve always been this way. Deal with it. I’m messy.” Slothfulness and laziness are not temperament traits. They are character flaws that have never been developed. If tidiness is important to you, this could be a watch out. Are you prepared to accept this trait in your mate?

When he’s never on time

Tiffany was frustrated with Jacob’s frequent tardiness. “He was always late for dates,” she said. “It wasn’t uncommon for me to show up at a restaurant only to get a text from Jacob saying he was running behind. He’d finally show up 30-40 minutes later profusely apologizing with an elaborate excuse. He promised to change, but he never did. Sometimes he’d send flowers the next day. It was as if he thought flowers should compensate for his lack of consideration.”

Like tidiness, punctuality is not part of our temperament. It’s a character trait that we choose to develop. It’s something that can be changed, but Jacob proved by his actions that he wasn’t interested in changing. “His tardiness translated disrespect and a lack of honor for me,” said Tiffany. “For me, it was a deal breaker.”

Relationship Risk Assessment© (RRA)

Below you’ll find two tools. One is a character quiz and the other is my Relationship Risk Assessment. You can download the RRA in a moment, but here’s what it looks like.

I compare the quiz and the RRA to a railroad crossing. When you approach a crossing, you exercise more caution. If the lights are blinking and the arms are going down you run a great risk if you try to cross in front of a train. There’ll be a huge collide if you ignore caution. I also compare the RRA to the prudence lenders use in reviewing a loan applicant. A borrower’s credit score doesn’t have to be perfect to get a loan. Lenders assume a moderate amount of risk in most transactions, but by checking a borrower’s credit, they can use wisdom to review the risk. They’re wise and selective about whom they loan money to. If the risks are too high, the loan is denied.

Likewise, in relationships, it’s important to consider the risk. It’s the uncertainty and ambiguity that’s dangerous. Knowing the risk factors will help you evaluate whether or not you are prepared to accept them.

The character quiz will allow you to consider how your guy stacks up in regards to 33 different character traits. You ask yourself, “Is he….?”

Ambitious     Attentive      Confident
Careful     Sympathetic     Respectful
Generous     Considerate      Grateful
Creative     Resolved      Reliable
Diplomatic      Tidy     Influential
Flexible     Intelligent     Hardworking
Strong in faith     Forgiving     Polite
Honest     Hopeful      Loyal
Compliant     Organized     Patient
Punctual     Thrifty     Hospitable
Responsible     Peaceful     Ready for a relationship

You can take the quiz in a minute, but first let me tell you about the Relationship Risk Assessment (RRA). The RRA takes character into consideration but also helps you consider you compatibility in regards to five key areas that I call the 5 F’s: faith, family, friends, finances, and fitness.

Chapter 16 in my book Love Junkies: 7 Steps for Breaking the Toxic Relationship Cycle provides more insight on this subject and discusses the 5 F’s in detail. You can purchase a copy here or on Amazon. Each of the 5 F’s provides several aspects of each category for you to consider your compatibility.

At the bottom of the RRA, you’ll see a spot to write down your top ten character traits in the spaces numbered 1-10. Look over the list of the 33 character traits above and select ten that are most important to you.

In the right hand column, you’ll notice there’s a place for you to comment on how you’ve seen each attribute evidenced. It’s important that you’re able to document evidence to affirm the existence of each quality so that you know you’re not just making an emotional assessment.

It’s also important to notate how you’ve seen unacceptable behavior evidenced. This will serve as a reminder to you should you be tempted to minimize the offense later, compromise or brush it off altogether.

After you’ve had sufficient opportunity to observe your date’s behavior and character, find a quiet time to review the checklist. Be honest and be picky. Committing to a life partner is the most important decision you’ll ever make.

When you’re finished with your RRA, look at where the majority of the checkmarks are. How did your guy rate? If there are deal breakers or if he doesn’t look good on paper, it’s best to use the wisdom of this exercise to dismiss the idea of pursuing a relationship. On the other hand, if his character and compatibility are in alignment with your desires, and he feels the same way about you, you have a great foundation for a successful relationship.

Remember, dating smart protects your heart. If you settle, compromise, rush and push, you’ll only produce a knock-off relationship that won’t survive hardships. But when you use wisdom to evaluate character and compatibility, you’ll stand a much better change to enjoy a healthy relationship and satisfying marriage.If you’d like more wisdom on dating, contact me at for a one-on-one coaching session or pick up a copy of Love Junkies, 7 Steps for Breaking the Toxic Relationship Cycle.

Ok, so here’s the quiz:

Now select your top ten character qualities and click here to print your copy of the Relationship Risk Assessment.

When you use these tools you’ll be better equipped to date heart smart! 

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