Oct 35 min read

I Tried Dating, But It Never Goes Beyond the First Date—Here’s What I Learned About Why

Have you ever met someone at a singles event, felt a little spark, and thought, “Maybe I should ask this person out?” So, you muster up the courage, go on a date… and then… nothing. Maybe it ends with an awkward goodbye, or worse—one person ghosting the other.

I know how frustrating this can be. I've had my fair share of first dates that didn’t lead anywhere, I’ve often wondered: What went wrong? Was it me? Was it them? Or was it something else altogether?

It took a while, but I’ve started to realize that sometimes, it’s not about the people or the chemistry—it’s about our approach to dating. So, I want to share some of the roadblocks I’ve faced and the small mindset shifts that have helped me and others in this community see dating in a different light.

If you’ve ever found yourself asking, “What should we even do on a date?” or felt like you’re stuck in a cycle of one-off dates that don’t go anywhere, maybe these insights can help.

Roadblock 1: “What Should We Do on the Date?”

Solution: Communicate and Explore Shared Interests

One of the most common struggles I’ve heard from both guys and girls is figuring out what to do on a date. As a girl, I used to wonder if I should just let the guy plan everything, hoping he’d get it right. But that often left me feeling like I was just a passive participant in the date rather than an active part of building the experience together.

Then, I started to ask myself: Why don’t I speak up about what I like?

Dating shouldn’t feel like a guessing game. Communicating openly about what you might both enjoy is actually one of the best ways to show respect and consideration for each other. For example, instead of saying, “I’m fine with any activity,” I’ve learned to say, “I feel more relaxed when we walk and chat in open areas like a park. Would you be up for a stroll through the park after dinner?”

It’s a small change, but it makes a big difference in setting the tone for the date. It’s no longer about one person trying to figure out the other, but about finding shared experiences that allow both people to feel heard and valued.

Roadblock 2: “Everyone’s Doing the Same Thing—How Do We Make It Special?”

Solution: Create Your Own Experiences and Let Go of Comparisons

It’s easy to get caught up in what other couples are doing. Sometimes I see friends going on exciting dates—staycations, fancy restaurants, or unique workshops—and feel this pressure to “keep up.” So, I’d end up choosing activities that weren’t really “me,” just to create that ideal dating experience.

But I’ve come to realize that dating isn’t about fitting into a mold. Singapore may be small, but there’s still room to create unique experiences if we’re willing to think outside the box.

What do we do when there are memories that linger in familiar spaces? Singapore is small, and there’s no escaping that. Chances are, any place you go has some kind of history—either for yourself or for the other person. I’ve found myself avoiding certain places because they reminded me of past dates or experiences with people I didn’t end up with. But should we really avoid all these spaces just because of old memories?

I think it’s worth revisiting some of these places to create new memories. Because if we’re honest, it’s not about the venue. It’s about how we choose to approach it now, in the present, with a new person. Maybe you used to love going to East Coast Park with an ex, but that doesn’t mean you can’t enjoy a different experience there with someone else. It’s about allowing old places to have new meanings. That’s what I hope we can all embrace.

Roadblock 3: “Do Dates Have to Be Expensive to Be Meaningful?”

Solution: Reframe Your Budget and Redefine the Purpose of a Date

The truth is, it’s easy to fall into the habit of expensive dates in Singapore. With cafes and restaurants sprouting up everywhere, I’ve felt the temptation to think that a “nice” date has to come with a high price tag. But after a few $100 dinners, it dawned on me—this is not sustainable. Not only that, but it also made me wonder: Is this really how I want to build a relationship?

The purpose of a date isn’t to impress someone with what you can afford, but to get to know each other better. Hawker centre or Kopitiam meals might not seem “romantic,” but sharing a meal at a place where I feel most at home created a kind of intimacy that fancy restaurants didn’t. It showed the other person a part of my daily life, and it gave us the space to connect over what’s really important: our values, our stories, and our aspirations.

Setting a budget doesn’t have to feel like a restraint—it can actually be an opportunity for both people to brainstorm, discuss, and work together on something, almost like a mini project with a shared goal. It becomes less about the limitation and more about the experience of making joint decisions, understanding each other’s preferences, and creating something meaningful within those parameters.

Roadblock 4: “How Do We Build Authentic Conversations on Dates?”

Solution: Create Space for Vulnerability and Include Your Faith

I think one of the biggest struggles as Christian singles is wanting to dive deeper in conversation, but not knowing how. It’s easy to keep things light, but harder to create space for authenticity. I used to feel like I had to save the “serious talk” for later dates when we’re more comfortable. But what if that means we’re missing out on meaningful conversations that could build trust and connection?

I’ve found that starting with small shares of your own journey can pave the way. Talking about what God has been teaching me, or a verse that’s been on my heart, often opens the door for deeper conversations. It’s not about turning the date into a faith session, but simply allowing faith to be a natural part of the dialogue.

If you are dating more seriously* (i.e., both have indicated mutual interest to continue exploring a relationship)... I would suggest for either one of you to end a date by saying, “Would it be okay if I prayed for our week ahead?” It’s not always easy to bring up, but I’ve realized that if faith is integral to who we are, then it should flow into our dates as well.

*Note: I mention this specifically for those in more serious dating stages because prayer can be quite personal, and not everyone may feel comfortable engaging in it one-on-one with someone they’ve just met. If it’s only your first or second date, consider starting with a simple prayer of thanks before a meal to keep it light and approachable.

Want to Experience This First-Hand? Join Us for Our Jewel Hunt!

If any of these roadblocks resonate with you, and you’d like to practice overcoming them in a fun, supportive environment, we have just the event for you!

Join us for our Jewel Hunt on 12 October! This event is designed to help Christian singles navigate date-planning challenges while keeping the focus on meaningful interactions.

Through a series of challenges, you’ll get to help our fictional couple, David and Sarah, decide on snacks, activities, and entertainment options—all while keeping to a budget.

By the end of the event, I hope you’ll see that it’s not about the venue or the budget, but the genuine conversations and shared experiences that make each interaction meaningful.