How God Encouraged Me When Dating Didn’t Work Out

By Emma*, as told to Rachel Tso

I was excited when he—let’s call him John—asked me out.

We had known each other for a long time and did ministry work together. He had a heart for God, people, and missions, and was fun to be around. Our friends also told us that we had good chemistry, so I made the effort to spend more time with him, even offering to organise activities to do together.

He then took the initiative to ask if we could get to know each other on a one-on-one basis, since we had only been interacting in group settings all this time. This dating period was meant to help us decide if there could be something more between us.

We went on a few dates for a couple of months, which I really enjoyed. Then one evening, he told me that he wasn’t sure about us, and that he had a lot of things going on. This confused me, since we had been going on dates all this while, I figured that he should at least like me. But he said he wanted to take a break for a few weeks.

Then, at the end of the break, he decided to end things completely. What was devastating was hearing him say he wasn’t attracted to me romantically. Never had I felt so rejected.

When My Hopes for a Relationship Was Dashed For a good half year, I had been trading messages with someone I had just gotten to know. Wisdom gleaned from dating sites and friends had me convinced that he was interested in me—otherwise, why would he be messaging me every day? Surely, there had to be  an interest of some sort involved, right? “He might ask me out any day now,” I thought. Sadly, I was so wrong.

But how God met me in my pain following that experience was amazing, and it has forever changed my relationship with Him.

1. He helped me be fully honest with Him

Because I wanted to involve God more intentionally in this dating journey, I decided to start journalling.

Writing down my raw thoughts and feelings helped me put words to specific emotions and thoughts, which allowed me to ask God to further reveal why I feel or think the way I do—what was in my heart (fears, doubts, or lies from the devil). This enabled me to repent and pray for Him to realign my heart and motivations to Him.

While on the “break” with John, I ran to God all the more. I poured out to Him my feelings of rejection and unworthiness (that I wasn’t good, attractive, or loveable enough) and shed many tears. I felt no shame about approaching Him so honestly, expressing my anger and disappointment when I felt He wasn’t providing for me in this area. I realised that I didn’t need to put on a front before God who knows me fully (Psalm 139:4) and loves me perfectly.

Turning to God didn’t change my circumstance, but it changed me in the process, as He reminded me of who He is and who He created me to be. Communicating my deepest needs to Him helped me draw closer to Him than before. In the process, I also learned to be honest and vulnerable towards others, which I previously struggled with due to fear of judgement.

Give Yourself Permission to Grieve Truthfully, my heart felt raw, as if it were beating outside of my body. My grief felt so vulnerable, so scraped and skinned and gaping, that privacy was all I could fathom to deal with it.

I also went on lots of runs, and it helped clear my mind to think and pray. One day, I was running along a familiar route and stopped at a rest area. There was a tree nearby and as I sat and gazed at the tree, the image of Jesus hanging on the cross came to mind. I felt an invitation from God to rest at the foot of the cross—where Jesus had given His life for me, and now met me in my pain—and I felt ministered to.

Acknowledging my pain was the first step to healing. It was through this experience that I came to understand Psalm 147:3 first-hand: “He heals the broken-hearted and binds up their wounds.”

2. He placed a loving community around me

On the same evening John decided to end things with me, I called up my close friends from church to tell them what had happened. Their listening ear and ability to articulate my thoughts when I was in shock was just what I needed. My friends even organised an outing to spend time with me, comfort me, and help me process my thoughts and find closure.

Through our conversations, I was able to see my situation more clearly and I mustered up the courage to meet John one last time.

During our meetup, I shared my honest thoughts about our dates and how I felt our time together was handled. It helped me to be part of this final decision, to be able to air my thoughts, and to find closure.

A few months later, I met someone on a dating app, and we went out on a date. Later that evening, however, I felt confused and emotional; I realised I hadn’t completely gotten over John yet, so I called one of my friends, who reassured me that it was okay to take as long as I need to heal. I explained this to the guy I had just met, and thankfully he was understanding about it.

As I reflect on this experience, one insight that I’ve learned from a friend is not to make decisions when I’m Hungry, Angry, Lonely or Tired (HALT). I was still feeling a bit angry and lonely from the experience with John, and that pushed me to resume dating before I was ready.

I am so grateful for my friends who came alongside me and were much-needed channels of God’s presence and comfort during that dark season of my life.

3 Types of Friends We All Need I’m sure we’re all familiar with broken relationships. Perhaps these negative experiences might have tempted us into thinking that maintaining true and deep friendships are unnecessary and bothersome. But the Bible tells us that we are made to relate to others, and not live in isolation (1 Cor 12:12-27), as is evident from what we have experienced during the lockdowns around the world.

3. He helps me empathise with other singles

Today, I serve in a singles’ ministry and frequently reach out to fellow Christians singles.

I am passionate about helping them expand their social circles, so I am involved in organising get-togethers, and I’m so encouraged when people step out of their comfort zone to attend these events, even if it’s on their own. It’s wonderful to see that not only are they meeting potential life partners, but they’re also forming new friendships. It is a joy to walk alongside them and pass on the love and encouragement I’ve received from God and from my friends.

Being able to empathise with fellow singles enable me to support them as well as I can. As I relate to their struggles, I try my best to encourage them not to waver in their faith (or to settle for something lesser than what God has in store for them) but to continue to trust God in this area of their life. I also enjoy sharing with them good podcasts or books on navigating singleness that I come across.

I believe that my ministry would not be as fruitful if God didn’t let me go through these dating experiences. God really does have a purpose for each of our struggles.

It’s okay to still struggle 

I am back on the dating apps, but with a renewed perspective that, if the other party isn’t into me, then there’s no need to push on with the relationship. I also learned that it is not wrong for me to feel that I deserve someone who likes me and is intentional in pursuing me.

I still struggle at times with my singleness, and some days can feel more hopeless than others. Whenever I see success stories around me, a part of me celebrates with them, but another part of me feels as if I’m not good enough. And after a while, there’s also a dating fatigue from constantly being on these apps, but still unable to find a potential suitor.

At times like these, a question I ask myself is, “How do I find the balance between being surrendered to the point of being okay with singlehood for the rest of my life, and holding out hope that God will eventually bring an end to this season of singleness?” It’s hard to find that balance, because it’s hard for me to say that I would be okay with remaining single.

But perhaps both longings are good, and it’s okay to feel either one of them, because they point to our deepest longing for God—not just in relationships but in all of life (Romans 8:22-23).

Through all these doubts, God always reassures me. He who created me—and the entire universe—loves me profoundly and is in a deep relationship with me that will never change or end.

As I learn to rest in this reassurance, I’m striving to trust God and live to the fullest in whatever status or stage of life I’m in. I still have hope that God will bring me someone, but I don’t want a romantic relationship to be the only goal in my life.

My mentor shared some advice I found liberating: “Don’t wait for marriage for your life to start. Do things that you enjoy right now.” I have a job that I enjoy, I deeply enjoy serving in church and in singles’ ministry, I enjoy spending time with my friends who are always fun and encouraging. If God calls me to marriage, I will be ready for it. Until then, I’m going to find joy in this moment.

I want to trust that God’s purpose and plans are better than my dreams. Even if no one comes along, I pray that I will experience His grace in my time of need throughout my days of singleness.

The book of Psalms has given me much hope and encouragement. Reading Psalm 27:13 has fortified my faith in God’s goodness: “I remain confident in this: I will see the goodness of God in the land of the living.” In my season of waiting, He is with me and will never leave me behind.

*not her real name