5 Principles For When Your Date Has Issues

When Your Date Has Issues

Today’s post is inspired by a Stump The Chump submission from Lauren. If you’d like to submit a question to Stump The Chump, click here.

Lauren writes,

“I have a question about a friendship of mine. Well, kind of. I went on two dates with a guy I met online. The first was great, fun, and normal. The second date was also great, but this guy shared very deeply about his past relationships, sins, and emotional issues. I wasn’t going to bring up too much about my past relationship on the second date, but I almost felt obligated because he initiated the deep discussion. Afterwards, we both definitely felt much closer emotionally. We said goodbye, and he told me he wanted to get to know me better. The next day, he invites me to different activities. I had to decline because of my job. Then, he calls me to say that he cannot be in a relationship with me or pursue me because he is a “mess” and needs to figure things out. He wants to take things more slowly and be friends, but HE is the one who initiated all the deep stuff! I just followed his lead.

“Question: do I totally forget about this guy? He invited me to another event. After that phone call, would it be wise for me to go? I like him and would definitely want to get to know him better.”

Thanks for the great question, Lauren!

Lauren is essentially asking, “What should I do when someone I like has personal issues that prevent him from pursuing a healthy relationship?” Many people have faced and will face this situation. We all face emotional, relational, spiritual, or personal issues at one point or another in life. So should we reject a person who hasn’t resolved all their issues yet? Should we give him or her a chance? What should you do when your date has issues?

#1 – Be Compassionate

I want to start by saying the attitude of heart we should have toward a person who has issues is one of compassion. This is because compassion is an expression of love. It’s right for us to have compassion on another person facing the weakness of personal issues, remembering that God has had compassion on us in the midst of all of our own weaknesses and shortcomings. Just as God hasn’t condemned us but invited us to find healing and transformation in Him, it’s right that we should encourage another person to pursue personal wholeness without having a condemning attitude.

Galatians 6:2 says, “Carry one another’s burdens, and in this way you will fulfill the law of Christ.” You probably won’t find yourself in a position to help a date work through his or her issues. Romantic entanglement is a bad environment in which to try to help a person resolve personal issues. That’s something he or she usually has to pursue apart from you. But by simply encouraging him or her to pursue that course, you can play a part in “carrying the burden” in a Christlike way.

So compassion is the proper attitude from which to engage a romantic interest who has personal issues.

#2 – Know That Health Is Necessary

Now we need to have the more sobering discussion. Reality is that it takes two healthy people to build a healthy relationship. I’m not saying either person should be perfect. That’s impossible. But there’s a big difference between a spiritually, emotionally, and relationally healthy person who makes mistakes and a person who has significant, unresolved personal issues that prevent him or her from pursuing healthy romance. The thing we have to come to grips with is that a person who has unresolved personal issues that make him or her relationally unhealthy CAN’T build a healthy romantic relationship with you.

It’s all too easy for us to minimize or rationalize issues that a person has, hoping they won’t prove troublesome in a romantic relationship. But the truth is that unresolved personal issues always break the surface. Ignoring issues doesn’t ever make them go away. It merely gives them to space to remain.

So the question we come to is, “what should we do when we know a romantic interest has issues that need to be resolved before he or she can proceed with a romantic relationship?”

#3 – Don’t Get Pulled In

When your romantic interest has unresolved issues, don’t get pulled into them! Some people will attempt to pursue romantic  relationships even if they’re not truly healthy enough to do so. You might be attracted is such a person (yes, people with unresolved issues can be attractive). The resulting temptation is to get relationally and emotionally entangled with him or her even though the issues are still present. Doing so is a bad idea! Getting romantically entangled with a person who needs to resolve personal issues rarely helps him or her resolve the issues. That process usually needs to be done independently with the help of a counselor. Getting entangled with an unhealthy person usually only draws you into dysfunction.

Lauren described an example of this when she described the second date she had. Her date shared deeply personal things about his emotional, relational, and spiritual struggles. Going so emotionally deep that early in a relationship isn’t healthy. Emotional connection needs to remain on pace with the development of the rest of the relationship. But note what happened. Even though Lauren didn’t want to reveal deep emotional or relational information on the second date, her date’s actions inclined her to do so. He pulled her into his unhealthy behavior. Note what else happened: Lauren said they felt emotionally closer afterward. That’s because revealing personal vulnerability naturally promotes emotional closeness. It’s part of how we humans are wired. However, just because sharing deeply personal things early in a relationship may make you FEEL connected, it’s still unhealthy.

So when you realize your romantic interest has unresolved issues, it’s essential not to let yourself get pulled into them. Now, maybe like Lauren you’ll get pulled in suddenly when you don’t expect it. After all, you can’t control what your date talks about! If you get caught off guard, don’t hold it against yourself. But as soon as you can, recognize that your romantic interest has issues and do what’s necessary not to get pulled in. That might mean having an honest conversation with your romantic interest about what unhealthy patterns you see emerging and how you’re not willing to participate in unhealthy behaviors. That brings us to the next point.

#4 – Expect Healthiness

It’s never wrong to expect healthiness in the relationships you choose to build. It’s right to express to a romantic interest that, while you don’t condemn him or her for having personal issues, you expect him or her to resolve significant issues before you’re willing to pursue a romantic relationship. In that conversation, you can encourage him or her to do what’s needed in order to resolve issues and become healthier while also making it clear that you’re not willing to go any further in a romantic relationship before that happens. If the person resolves the significant issues, then the two of you might be able to pursue a romantic relationship at a later time. However, it might also mean that you won’t have any further romantic relationship with this person. This should always be the case if a person refuses to deal with his or her issues. Remember, no matter how much you like a person, don’t settle for an unhealthy relationship!

#5 – Don’t Stay On The Line

I want to mention one more principle in light of something Lauren mentioned. In Lauren’s case, she didn’t have to talk with her romantic interest about pausing their relationship, because he called and said that he can’t continue to pursue her given his issues. But then he invited her to another event “as a friend.” Lauren likes him and still hopes they could possibly one day have a healthy romantic relationship. But should she spend time with him “as a friend,” hoping one day they could be more than friends, while knowing he’s paused their romantic relationship because of his issues? Doing so would be very dicey.

You know how you can keep a fish on the line when you go fishing? Think about it. When you have a fish on your fishing line, you can pull the fish into the boat and keep it, you can throw it back, or you can let the fish stay on your line indefinitely.

This fishing image can help us understand what’s happening between Lauren and her “let’s be friends because I have issues” guy. He’s not ready to pursue Lauren romantically (like taking a fish into the boat). But he also doesn’t want to end all contact and let Lauren move on (like letting a fish go free). Instead, he wants to spend time with Lauren “as friends” without making any sort of commitment to pursue her. Using the fishing metaphor, he wants to keep Lauren on the line indefinitely. This would be an unhealthy thing to accept. It’s unhealthy because it keeps Lauren in a place where she has a continued romantic attraction to this guy, hoping one day they’ll continue a romantic relationship, while there’s no promise that will ever happen. Things might be different if the guy commits to working through his issues and pursuing her on the other side of that process. But it’s very unwise to continue spending emotional energy on a person who may never resolve his or her personal issues and commit to pursuing you. Don’t stay on the line.

The decision not to stay on the line means having an honest and firm conversation with your romantic interest. You express that you’re not willing to stay in the emotionally unhealthy place of desiring to pursue romance with him or her, while he or she makes no promise of doing so. This doesn’t necessarily mean closing the door on any possibility of a future romantic relationship. It means you clearly express to your romantic interest that you expect him or her to actively work through the unresolved issues and then pursue you or else let you go and move on. Such a conversation might look something like this:

“[Name of interest], I need to be honest with you about what I want for our relationship. I like you, and I’d like to explore the possibility of us dating. But I know you’re not ready to pursue a relationship with me because of [unresolved issue]. It wouldn’t be emotionally healthy for me to keep spending time with you as a friend, wishing we were more than friends but knowing that can’t happen with things the way they are. So I need to take a step back from spending time with you just as a friend. I hope you’ll keep taking steps to resolve the issues you’ve mentioned. If you come to a point where those issues are resolved and you’re ready to pursue me, then you can call me. We can talk about possibly picking up where we left off. But apart from that, it’s not healthy for me to stay in an ‘in between’ friendship.”

Then finish the conversation with your romantic interest. Maybe he or she will express eagerness to pursue wholeness and build a future relationship with you. Maybe he or she won’t. Maybe he or she will complete the process of pursuing wholeness. Maybe he or she won’t. Whatever happens, take a step back from that person for the sake of your own emotional health. Don’t stay on the line! Move on. If he or she becomes healthy and the two of you later pursue a romantic relationship, awesome! Otherwise, move on and don’t look back. You deserve to have a healthy relationship that encourages you to be healthy. Don’t miss out on building a wonderful, healthy relationship with another person because you’re staying on the line for a person who isn’t doing what it takes to become the healthy partner you deserve.

I hope all this is helpful for you, Lauren, and for everyone who faces similar situations!

A Note For Anyone With Issues

By the way, if you’re reading this post and know that you have personal issues you haven’t fully resolved, I don’t want you to feel at all like you’re a person to be avoided. We all know that resolving personal issues can be a difficult thing that takes time. All of us have to work through personal issues at some time in our lives. We’re all cheering and rooting for you as you face the issues in your life and pursue wholeness! We’re excited to see the healthy, attractive person you’re becoming more and more with each step you take! Don’t be discouraged if you still have some steps to go. Don’t give up until you finish the journey to wholeness! You can do it!


What do you think? Have you been interested in a person who had unresolved personal issues? What can others learn through your story? Please share your thoughts with us in the comments!

And please share the post by using the buttons below!



  • Great post! I like it, I have had to face this at one point in life, but unfortunately I don’t think I refused to stay in the line in a good way like you just adviced Lauren to. For me, it was an ex boyfriend, who had personal issues but then again wanted to stay friends with me…but I knew I wasn’t ready to abuse myself emotionally like that, I just told him ‘I am sorry we can’t be friends, let’s just stick to how we behaved after the break up’ gosh, I am only feeling the harshness in that line now, and just wish I knew then what I know now…:-compassion! But then it’s ok, I am learning everyday.

    • Justin Megna says:

      That’s right, Nowani. Learning is a process. We all have memories of things we could have handled better. The important thing is to learn, forgive ourselves and others, and keep moving forward.

  • Jill Frey says:

    Spot on, Justin. Things happen in everybody’s past, we are all imperfect people. It’s normal to have issues, and only does a body good to work through them.
    A really good thing to do if a person recognizes the need to work on resolving their “baggage/issues”, is to concentrate on building healthy, safe friendships with safe people, of the opposite sex specifically, that are NOT based on romance (and probably not intentionally with any former boy/girlfriends!). It’s through these safe relationships that a person can best work towards and practice good habits and behaviors, without the degree of risk and uncertainty that is inherent in any dating relationship. If you’ve been hurt, faced your past, and grown through it, you can also decide to be that safe person.
    I would go so far to say that if a person is currently digging in their past, facing it, and is doing the hard work of changing from the inside out (which is AWESOME and so good and so difficult and God-honoring and POSSIBLE), they might need to abstain from dating completely for the time being and instead focus on what’s most important – maturing and getting healthy, building those safe relationships and support systems. I think that’s the best way. I know you alluded to this several times in the post, Justin, but maybe not speaking directly to someone who’s learning they’ve got baggage. The fisherman, I mean, not the fish.
    I bet it was really difficult for that guy to both admit to his issues and then to say no to continuing the relationship. It shows a degree of budding maturity realize that, and then act wisely on it.

Leave a Reply

Your email address will not be published. Required fields are marked *