Single Men and Dating: Character Questions to Ask Yourself

If you’re a single man, has a particular woman caught your attention? Perhaps you’re interested in pursuing her—you’ve noticed her character and warm smile, and you want to get to know her better. But are you ready to date? What are some practical character questions that you, as a single man, should ask yourself before you begin dating?

In the classic Disney film, Bambi, Friend Owl describes to Bambi and his companions the nature of a particular experience:

Yes. Nearly everybody gets twitterpated in the springtime. For example: You’re walking along, minding your own business. You’re looking neither to the left, nor to the right, when all of a sudden you run smack into a pretty face. Whoo-whoo! You begin to get weak in the knees. Your head’s in a whirl. And then you feel light as a feather, and before you know it, you’re walking on air. And then you know what? You’re knocked for a loop, and you completely lose your head!^[1]

In modern dating culture, this is the kind of captivating, energetic, emotional chaos that sparks and fuels romantic relationships. “Why are we dating? Because, in the best way possible, she has me completely losing my head!” This type of consideration regarding dating is what I’ve begun calling “The Twitterpated Experience.”

I want to propose an alternative biblical thought process for dating: engaging in reasonable deliberation about advancing toward marriage.

English clergyman John Angell James made this helpful statement in his piece Thoughts on Finding a Marriage Partner:

If the duties of this state (marriage) are so numerous and so weighty, and if the right discharge of these obligations as well as the happiness of our whole life . . . depend, as they necessarily must do, in no small measure upon the choice we make of a husband or wife, then let reason determine with what deliberation we should advance to such a connection.^[2]

As we consider the concept of dating from such a perspective, let’s look at four practical character questions that every man should ask himself before dating.   

Character Question #1: Are You Taking Responsibility?

Do you acknowledge that your ability to mature as a godly man is rooted in the powerful work of the Spirit and not in your circumstances?

A common view of self in today’s culture is that your development is completely controlled by your circumstances. Do you believe your environment determines your character and behavior? Do you consistently blame your poor character or sinful behaviors on others? When you ask character questions, are you targeting your own heart and actions or those of others?

Jesus makes it clear that, because “he who is in you is greater than he who is in the world,” we Christians can truly and consistently act righteously and with love regardless of circumstances or how others may act toward us (1 John 4:4). Why? Because in all circumstances we remain sustained as God’s loved children!

If you’re a single Christian man looking to date, you should be developing in taking personal responsibility for your actions. By God’s grace, you should be growing in upholding righteousness, love, and a joyful countenance towards others in all circumstances—even when others fail you or sin against you.^[3]

Character Question #2: Are You Growing in Patience?

Are you maturing as a patient man, specifically expressed in sympathy?

Theologian Herman Bavinck helpfully establishes the reality of the distinction between men and women:

This distinction was neither a human discovery or renovation, nor a product of circumstances, nor the result of a slow and gradual evolution, but has existed from the very beginning, provided by nature itself and consequently called into existence by God, who placed it before our eyes as an undeniable fact.^[4]

Bavinck also upholds the two sexes’ shared identity as image-bearing humans:

We must maintain, with the help of Scripture which alone supplies an explanation regarding the origin and essence of a human being, that both man and woman are created in God’s image, and therefore both are human beings in the fullest sense of the term.^[5]

Poorly lived out singleness establishes an environment where self-centered immediacy can go unchallenged, taking habitual root and creating an individualistic, unchallenged, self-empowered freedom to do “what I want to do, when I want to do it.” This goes against the process of slowing down to prioritize the investment in and pursuit of sympathy, which relationships need for shared development.

If you’re a Christian man looking to date, be developing a character that recognizes the fundamental need for patience. Only patience can facilitate learning, listening, and sympathizing with another valued image-bearer whose experiences are, in certain ways, different from your own. Your ability to love another will always fall short if it’s not shaped by a compassionate commitment to patiently pursue genuine understanding and consideration of their perspective (1 Cor. 12).

Character Question #3: Are You Pursuing Christian Unity?

Are you prone to gossip and undeveloped in confessing your sins and seeking forgiveness?

The Apostle Paul establishes Christian unity to the degree of intimacy where believers all are of one body and therefore, “If one member suffers, all suffer together; if one member is honored, all rejoice together” (1 Cor. 12:12–26). This depth of unity is also applied to marriage: “In the same way, husbands should love their wives as their own bodies. He who loves his wife loves himself. For no one ever hated his own flesh, but nourishes and cherishes it, just as Christ does the church” (Eph. 5:28–29).

Gossiping and lack of repentance are two sides of the same coin, and that is destructive individualism. Lack of repentance is a hypocritical unwillingness to confess, seek forgiveness, and turn from sin. Instead of acting in destructive individualism, you are to handle the sins of others with care, compassion, and discretion. You are to confess your sins against others wholeheartedly, promptly, and with sincerity as you pursue forgiveness and seek to re-establish right living. Why? Because mishandled sins, originating from either party in a relationship, compound the suffering of all those in the relationship and choke out nourishing love.

If you’re a single Christian man looking to date, ask character questions that examine whether you’re growing in mastery over your actions and the words you use to describe the actions of others. Strive, in word and deed, to build up and not tear down as you recognize that, in the context of relationships, acts of edification and degradation are of mutual impact.

Character Question #4: Are You Seeking Instruction?

Do you have a humble heart to embrace instruction, counsel, and correction through honorable relationships with godly fathers within godly families?

God has called both biological families and the spiritual family of the church to maintain a unity of biblical beliefs, practices, and worship through a generational downflowing of parental instruction. The Apostle Paul rooted his confidence in Timothy to “flee youthful passions and pursue righteousness, faith, love, and peace, along with those who call on the Lord from a pure heart” upon the premise that Timothy had been entrusted with a “good deposit” through the instruction of his spiritual father, Paul himself. Furthermore, it is that same “good deposit” Timothy received from his spiritual father which he is instructed by Paul to “entrust to (other) faithful men” (2 Tim. 1–2).

A single Christian man who wants to date should be growing in his commitment to humbly and honorably receive the “good deposit” brought to him through fatherly discipleship in the home, when accessible, and in the local church (Titus).

When my wife and I were married, the first passage I picked to have read during our ceremony was Matthew 1:1–17, a genealogy—meaning it was entirely a list of names. The last verse in this passage reveals why I chose it: “So all the generations from Abraham to David were fourteen generations, and from David to the deportation to Babylon fourteen generations, and from the deportation to Babylon to the Christ fourteen generations” (Matt. 1:17). From the beginning of history to its end, from the Old Testament to the New Testament, from father Abraham to father Paul, God is using the biological family and spiritual family to carry on the “good deposit” of Christ Jesus from one generation to the next. My wife and I see our marriage as us uniquely entering our new place as shifting participants in a bigger picture of God’s His-story.

Single Christian man, if you’re looking to date, start asking character questions focused on developing a legacy-oriented vision for your participation, in your union with Christ, in your family and local church. Learn to see yourself in your appropriate place as a particular receiver and giver of the “good deposit” found in Christ alone.

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^[1] Watch the Bambi clip.

^[2] Scott T. Brown and Jeff Pollard, A Theology of the Family, 259

^[3] Upholding righteousness, love, and joy towards others in all circumstances does not mean subjecting yourself to abuse. If you’re in an abusive relationship, please promptly seek help from the proper caretakers and authorities. 

^[4] Herman Bavinck, The Christian Family, 64

^[5] Ibid., 66