Unsure About Dating Someone? Here’s What to Do Next

Let’s face it, sometimes you’re unsure whether you want to go out with someone or not. You are single and want to be married, but you have mixed emotions about a certain person. Part of you thinks they're cute, and part of you doesn't. Part of you sees potential in them, and part of you thinks they'll be a dud.

You might be saying to yourself, "I want to go on a date with this person and find out if it will lead to marriage," and the other voice of you says, "Nah, I'm really not interested in them. Plus, starting something isn't worth the pain if it ends."

I'm thinking of the late 80s song by the Rolling Stones titled, Mixed Emotions, which is all about ambivalence in romantic relationships.

When you're torn about giving a date or two a try or not, what do you do?

Mixed emotions and uncertainty in dating are normal. Dating is about spending time with someone for the possibility of marriage, but the keyword here is possibility. A relationship might or might not go to marriage, but dating is how you find out.

Get on the Train or Not?

Dating is like going on a train ride. To go on one date is like buying a ticket and boarding the first stop. The next stop on the train's line is equivalent to going on another date.

The train's final destination is marriage, but at each stop, you can choose to buy another ticket and go to the next stop or exit the train and end your journey.

Commitment, intimacy, and a deepening of the relationship increase as you go further down the track. The longer you're on the journey, the closer you are to marriage. But, the more distance you travel, the more pain you'll experience if one or both you get off at a stop down the line.

The question is, do you even want to buy a ticket and go on one date? Or, would you like to get to know the person and travel to a few spots together?

Here's what to do when your heart is split.

Is There Any Possibility for Marriage?

Like the train's final destination, the purpose of dating is to get to marriage. First ask yourself, "Is there even an inkling within me for the possibility of marrying this person?" Is there a tiny spark or an iota of interest? There's no such thing as platonic dating.

If you have a quiet butterfly or two in your stomach, go on a date—"buy a ticket." The worst that can happen is that you spend a few hours with someone, get to share about yourself, and learn about someone else.

If there's absolutely no chance of marriage, then don't—don't even get on the train.

I would challenge you by asking, if you're not attracted to them, could you be? Attraction can grow. If their character is mature, they love the Lord, and have a heart to serve, could a nascent attraction shine through by spending time with them?

Again, this is up to you. If 100% no, don't waste your time. But I would at least think twice about passing up going on a date with an amazing person that, at least at first, you're not hot and heavy over.

Are You Curious?

Dating is about answering your curiosity. Curiosity is that itch that you need to scratch. You look at the person and ask yourself, "I wonder if they'd be a good match for me?" "I wonder if what we form together would be good for both of us?"

Itches are good. They mean you're curious and want more information. If you are excited to find out, jump on that train and see! But if you're feeling in between, you have to decide whether you want to go on a few dates with them.

In 99% of cases, you won't know you want to marry them without going on at least a few dates—those men and women are blessed to know so early! Praise God for times like this, but so far, this hasn't been what I've experienced in my romantic journey.

Most of us will need to go on at least one date to find out if there could be more than friendship.

Or, put another way, curiosity is about gaining information. You have questions about them you want answers to. You want to get to know them, and this getting-to-know-them process is dating.

It all begins with curiosity—Could they be 'The One?' If you have curiosity, go on a date and get the info you need. If you don't have any questions about them or already know they are not 'The One,' don't start anything.

Curiosity for marriage = date
No curiosity ≠ date

Again, if there's zero chance of marriage, and you have no curiosity, and if you already have all the information you need and have decided on friendship, save yourself the headache and don't go on a date.

How to Handle Mixed Emotions

What if you're torn and don't know what you want? Maybe you're sensitive like me and bond easily (and often too quickly), fear even one date will prick your heart. You hate the idea of going out with them and hurting someone. Proverbs 4:23 states, "Guard your heart above all else, for it determines the course of your life."

You get to decide whether your heart can handle a date.

When your feelings are split, you have two options: One, you can avoid the winds of ambivalence altogether, forgo going on a date or two, and try to forget about them. That's the safest option for your heart. In this space, talk to God about it, give it time, trust Him, get counsel, and avoid making a decision until you are certain you want to go on a date.

If you decide it's a "yes" to a date later, hope they are still single.

Or, you can not play it completely safe and just go on a date when the opportunity is in front of you. This is you trusting God in a different way. You know He is with you, and you can learn to fly the plane in the wind of uncertainty. Therefore, you can take a risk and go on a few dates, continue to pray, and see what develops with the person.

If you're 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

Tell the person you’d like to go out with them, but with a caveat that you're not sure what you ultimately want. You could 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 practice honesty and openness at the outset, you will build your relationship on the solid rock of truth, whether it leads to marriage or stays as friends.

If you know your specific hang-up, consider sharing it with them. One lady did this with me. I asked her out, she said “yes," and we went on a few dates. I noticed something was off, and she admitted, “I’m still trying to figure out if I’m attracted to you.”

Her words caught me off guard, but I appreciated her honesty and boldness. I'm secure enough to know that everyone won’t be sexually attracted to me, and to think everyone would be is prideful anyway. Someone's hang-ups about you don't say anything about your identity, because your worth is in Christ, not in someone's opinions. The fact that someone isn't attracted to me or to you amounts to zero on the scales of our self-worth and our value to God and others.

The same goes for being the one to share what's holding you back. They will appreciate your honesty and vulnerability. If they can't handle you speaking love in truth at the outset, they won't be able to hand when you have a real disagreement later on.

The point is, you can name the concern. It will give you peace and put to rest your anxiety if you go out on a date, but stop after that. You were clear, and you set the right expectations for the relationship.

You could share, "I want to live near my parents, and I know you want to do missions in Thailand. How would that even work if we started dating?" Only you can decide which values you're willing to hang on to and which you're willing to let go of.

Or, "I think you have a strong faith and solid character. I'm not sure if we could be more than friends, but let's go on a date and find out."

Even one date leads to deeper conversations about each person's vision for their life. Getting to know what's below the surface is the point of dating—to find out who they are and if you could see yourself marrying them.

One note about deciding yes or no, based on calling. Unless God has spoken to you 100% about when, where, and how your calling will be, don't say "no" to someone whose calling is different than yours. I talk more about matching on deeper values in Chapter 7 of my dating book, How Should a Christian Date?

Go on Three Dates

Another option when you're still deciding what to do is to go on three dates. 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, giving you enough time to interact with them and to decide whether you want more. If they ask you out, reply with a similar version: “Thanks for asking me. I’m not sure if I could use being more than friends, but I’m willing to go on three dates to see if there could be more.”

My friend did this with a few women 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 and planned it together. Each person made a small investment in the relationship while learning what the other preferred. Plus, you get to see how you work together as a team in developing the third date.

Now, he's married to a wonderful wife with two kids.

Set a Timeframe

Another solution when you’re torn is to set a time frame for the dating relationship. For example, agree to date for a month, and set a date for the D.T.R. (Define the Relationship) at the outset. Ask them, “What do you think about dating for four weeks, then we'll have an update? We can evaluate where we’re both at and see if we want to continue or not.”

After that, date and have fun. You don’t worry about deciding where the relationship is going until you have a safe space and a timeframe to find out. The whole point of this method, and the others, is to give you the freedom to get to know someone without worrying about whether you’re going to marry them or not.

In this time, stave off any physical affection. Holding hands and kissing will only cloud the relationship and will confuse your judgment. Wait until you know where the relationship is going. You're not just dating "as friends," but physically act like you're friends—especially because the relationship could end soon.

Guard your heart in this trial period, and help keep a clear head. If you both decide to officially be a couple and make a true run for marriage, then it's time to put your hands in the popcorn bowl at the same time.

Break Paralysis of Analysis

When you're unsure, be honest with them about your intention and set a limiting principle, such as three dates or a month-long timeframe. Following these methods when you’re unsure about dating someone will free your heart from the anxiety, because you know what you started is not something interminable if you want out.

It’s tough to navigate the grey areas in our hearts when you feel stuck. Action brings clarity, not contemplation. Read that again: Action brings clarity. If you’re stewing over them for months, unsure of whether to go out with them, it’s time to do something or say something about it. Making a move to progress your love life is much better than being stuck in a black hole of “paralysis of analysis.”

Taking action is risky, but so is waiting.

In the Bible, when Ruth provocatively lay at Boaz's feet, she took a big risk. When Jacob worked for Rachel’s father 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.

Move forward and get to know someone without the pressure of needing to know exactly what you want. As you spend time getting to know them, you’ll gain clarity and ultimately decide whether you want to move forward. But if you know after just one date that the relationship won't go past friendship, you are free to end it there.

>>Can Christian women make the first move? Here's what I think.