Christian Dating
Woman is unsure of dating a guy

Unsure of Dating Someone? Here’s What to Do

Let’s face it, sometimes you’re unsure whether you want to go out with someone or not. Ambivalence in dating—especially at the outset—is normal and expected. Dating is about spending time with someone for the possibility of marriage, but the keyword is a possibility. If you go out with someone, there should be at least an inkling that a relationship could start, and it could go to marriage.

The purpose of dating is to get you to marriage, but it’s OK not to be one-hundred percent certain that you even want to spend time with them. When this happens, you’re in two different places—part of you sees potential while the other part already believes it’s a “no.” Still, you’re curious enough to entertain the idea.

People are waiting longer than ever to get married. I think part of the reason is that people in the church are afraid to take risks to go on dates. They are scared that one date is tantamount to marriage or don’t know what to do when they have mixed feelings about someone.

When you are unsure but willing to take a risk, here are three ways to take action, soothe your uncertainty, and give you the information you need to see if the relationship could go further.

Communicate Your Uncertainty

I’m all for honesty and openness. If you practice this at the outset, you will build your relationship on the solid rock of truth. Tell the person you’re going out with that you’re struggling with indecision. If they ask you out, say, “I’ve never really thought of you as more than a friend. But I’m willing to spend time with you and see if my heart grows. Are you OK with that?”

If you know your specific hang-up, consider telling them your struggle. I asked out one young lady, and she said “yes.” Two weeks later, however, she admitted her ambivalence. One night I asked her where her heart was at, and she responded, “I’m still trying to figure out if I’m attracted to you.” Her words caught me off guard, but I appreciated her honesty. Be secure that everyone won’t be sexually attracted to you. That says nothing of your self-worth and value to God and others.

Go on Three Dates

Practically, consider going on three dates with the person you’re curious about. Communicate your idea for this trifecta from the beginning. If you’re the one doing the asking-out, say, “I think you’re great, and I’d like to get to know you more. What do you think about going on three dates and re-evaluating things after that?” This method sets a limit of three outings that will give you enough time to interact with them to determine if you want more. The same response also applies if they ask you out. Say, “Thanks for asking me. I’m not sure, but I’m willing to go on three dates to see if there could be more.”

My friend did this and had a clever way of planning each of the three dates. He’d arrange and pay for the first one, the woman did the same for the second, and for the third, they created it and planned it together. This is a helpful way for each person to make a small investment in the relationship while learning what each person prefers. Plus, you get to see how you work together as a team in developing the third date.

Set a Timeframe

Another solution when you’re unsure about committing to someone is setting a timeframe. You could go on dates for a couple of weeks, a month, or longer. But I don’t recommend doing this for longer than six weeks; otherwise, hearts and lives will get too emotionally tangled.

Like the previous three-date-method, set this expectation from the outset. Ask them, “What do you think about going on some dates for a month? At the end of that, we can evaluate where we’re both at?” After that, have fun and don’t worry about deciding until you have to. The whole point of these methods is to give you the freedom to get to know someone without worrying about whether you’re going to marry them or not. If you still have anxiety, you’re missing the point, or maybe you need to wait longer to act and figure out your fear.

Break Paralysis of Analysis

Overall, be honest with your intention and set up a limiting principle like three dates or a timeframe. Following these methods when you’re unsure about dating someone will free your heart from the anxiety so you can move forward and get to know someone without the pressure of needing to know exactly what you want.

It’s tough to deal with the grey areas in our hearts, but action elicits clarity. If you’re stewing over them for months, unsure of whether to go out with them, it’s time to act. Making a move to progress your love life is much better than being stuck in a black hole of “paralysis of analysis.”

In the Bible, when Ruth provocatively laid at the feet of Boaz, she took a big risk. When Jacob worked for Rachel’s for seven years, he couldn’t be sure that Laban would finally give away his daughter. Although Ruth and Jacob knew who they wanted to marry, they still had to take significant risks.

As you spend time and get to know the person you’re curious about, you’ll gain clarity and ultimately discover whether you want to move forward or not. But if you know after just one date the relationship won’t go past friendship, you are free to end it there.

What are your thoughts on what to do when you’re unsure about dating someone?

Check out my new dating book, How Should a Christian Date? It’s Not as Complicated as You Think.

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