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The Early Encounters

You’re out there. You’re meeting people. You’re doing the thing! But for some reason… it never seems to go beyond a first date.

Graduate this stage by: Going on second dates (go to next stage)

Your focus: Explore connections and start out as you would a friend

Activities to graduate:

  • After each date, journal your emotional experience (not just “did I like them?” but “how did I feel around them?”).

  • Say yes to a second date with people who aren’t “your type”— lead with the curiosity o what could be!

  • Go on fun, casual dates (like a Kopi Date!)

  • Practice asking thoughtful, open-ended questions with your friends

You’re probably facing one or more of the challenges. Click the ones you resonate with:

I don’t like them

  • The conversation didn’t flow.
    It felt awkward, similar to a job interview. You had to carry the whole thing or didn’t even know what to say.

  • Not the “right” one
    They are not what you’re looking for: different values, different vibes, different life goals, not your usual type, etc.

  • Felt no “spark”
    Nothing was wrong, but nothing stood out either so you don’t choose to pursue them.

I like them but they don’t seem to like me

  • They didn’t show interest in me
    They might have given short answers, avoided deeper connection, or maybe even hinted that they weren’t interested in pursuing things further.

I’m not sure how to proceed

 

The conversation didn’t flow.

Many people judge the conversation as if it’s fixed, but in reality, communication is something both people can improve.

What’s really going on:

Treating the date like an interview
You’re trying to figure out if they’re a “good fit” right away so you’re focused on “checking boxes”, rather than a human experience.

The setting didn’t help the conversation flow
Sitting across a table and trading questions can feel stiff and unnatural — like a job interview. It’s hard to relax or be yourself.

Lack of communication skills
Not everyone is naturally great at first-date conversations — it’s a skill, not magic.

Difficulty opening up
You might feel nervous or unsure about how much to share, making it hard for the conversation to flow naturally.

Fear of saying the wrong thing
You or your date may have been overly cautious, afraid of saying something inappropriate or awkward.


Lack of shared interests or energy
The conversation might have felt flat because you and your date just didn’t click in terms of interests or energy.


You seem open, but you’re not letting people in
You might be warm and talkative, but emotionally, you’re keeping others at a distance, maybe without realising it. That can make the conversation feel surface-level or flat.

What to try instead

Shift from “finding” to “discovering”
Let go of trying to assess your date. The goal of the first date isn’t to decide everything — it’s to see if you enjoy being around each other.

Try experience-based dates
Do something interactive like a walk, museum visit, or casual activity. Shared experiences take the pressure off talking and help connection unfold more naturally.

Model what you’d like to receive.
Practice asking better questions, listening actively, and being present. Guide the tone, bring curiosity, and give space for them to meet you halfway.

Warm it up & show childlike curiosity
Try sharing a little bit about yourself first, and then gradually encourage the other person to open up. Vulnerability often leads to more openness.


Be real, not perfect.
Let go of the fear of saying the wrong thing. HAVE. FUN.

Find common ground, not differences.
Look for small overlaps in interests or values that can spark more engagement. Don’t be afraid to talk about things you’re passionate about.

Practice emotional openness in small ways
You don’t have to spill your life story — but let people see you a little more. Share something honest. That’s what creates depth and connection.

 

Not the “right” one

Often, the hesitation to fully invest might be tied to a deeper emotional layer of fear and uncertainty.

What’s really going on:

You’re scared of making the “wrong” choice.
Maybe, you’ve internalised the idea that there’s a “right” one. This mindset puts huge pressure on every early interaction. You’re trying to decide the whole story in chapter one.

You don’t want to waste time or get stuck in something that won’t work.
You’re assuming things probably won’t work out, so you hesitate to invest more energy. But how can you know that after just one date? Cutting it off too early might mean missing something meaningful.


You’re thinking too far ahead
You’re not creating enough space for “maybe”. It’s either “hell yes” or nothing. To you, each decision feels final — like once you say yes, there’s no turning back.

You’re over-optimizing for “perfect”
Modern dating has taught you to believe there’s always someone better out there. You become hyper-focused on choosing “the best”— looking for the perfect fit on paper (lifestyle, career, timeline, personality).

You don’t really know what you’re looking for
You don’t have an inner compass to help you recognise if something’s worth continuing. So you rely on vague feelings like “spark” or “certainty” — which aren’t always reliable guides.

What to try instead

Let go of the “one” myth.
Focus on whether there’s enough curiosity to keep learning about the person. That’s all you need to know right now. Ask: “Do I want to learn more about this person?” instead of “Is this the one?”

Aim for discovery, not success or failure.
You don’t need to know how it ends. If there’s something you’re still curious about, it’s not wasted time — it’s learning. Even a short connection can be worthwhile if it teaches you something or helps you grow. Let it be part of your journey.


Reframe your decisions as soft steps, not hard commitments.
A second date isn’t a lifetime contract — you're just seeing if there's more to learn about this person. Give yourself permission to explore.


Loosen the checklist
Instead of filtering fast, give yourself time to build the connection. Choose to explore, not optimize. Curiosity over clarity.

*Pro tip: avoid the apps! Look for something more organic

Spend time getting clear on what matters to you.
Not a checklist — but what a meaningful connection looks and feels like.

 

Felt no “spark”

What’s really going on:

You expected instant chemistry.

Real relationships don’t always start with a bang. Sometimes the spark comes later, once safety and trust build.

You have an unrealistic expectation of love

You were hoping for something movie-like — big laughs, electric tension, deep conversations. Real connection isn’t always dramatic. Those “highs” from TV can be unrealistic and even misleading, blocking you from discovering real, grounded connection.

What to try instead:

Ask yourself instead:

Was I at ease? Curious? Comfortable? These are better signs than instant excitement.


Catch yourself. Are you chasing a feeling or a person? Let the connection unfold instead of judging it too quickly.

 

They didn’t show interest in me

What to try instead:

Build dating fluency

Dating is a skill. Learn how to ask better questions, share a little vulnerability, and tell stories that show who you are and what lights you up.

Grooming & presentation
You don’t need have everything perfectly styled, but a little effort shows that you care about yourself and the person you're meeting

Accept and move on
People are complex — they may be emotionally preoccupied, unsure of what they want, or just didn’t feel it. Don’t spiral into self-doubt. Instead, take it as part of the dating journey

What’s really going on:

Skills gap
You might not have shown the kind of presence or connection that makes a date feel meaningful like emotional presence, curiosity, storytelling, or attunement.

Negative first impression
How we present ourselves can influence how others perceive us.

Emotional Unavailability (on their end)
Even if you showed up fully, they might not have been ready to connect.

 

I’m scared of leading someone on.

What to try instead:

Let go of the outcome
Don’t feel like you have to make a decision too soon. Be open about where you are emotionally and let things unfold naturally without overthinking the “right” time to act.

Communicate your feelings honestly
Instead of pulling away, express your genuine feelings - people appreciate that more. Let them know you’re still figuring things out, but you’re open to exploring the connection. Setting clear boundaries and intentions helps avoid any misunderstandings down the line.

What’s really going on:

You're not trusting the process
You’re overly concerned about controlling the outcome or fearing what might happen in the future, so you pull back.


You’re afraid of disappointing someone else
You care about their feelings and don’t want to lead them on, but in doing so, you might miss out on a potential connection.

 

Unclear if your feelings are reciprocated

What to try instead:

Rejection therapy
Rejection is a normal part of dating and doesn’t define your worth. In fact, it is an opportunity for growth, not failure. Practice taking small risks in other areas of life to build your confidence.

Learn to recognize signals and ask openly
Pay attention to verbal and non-verbal cues to gauge their interest (eye contact, body language, or playful comments). If you’re unsure, simply saying something like “I’ve really enjoyed our time together. Would you like to do this again sometime?” can easily clear up any ambiguity.

What’s really going on:

You’re scared of rejection
You’re afraid that if you make a move, you might be rejected, so you hold back. This fear keeps you stuck in uncertainty and prevents you from fully exploring the connection.

You don’t know how to read the signals

You’re unsure whether the other person is interested, and you might be missing subtle cues (like body language or tone) or not sure how to ask directly.

 

Don’t know how to ask the person out

What to try instead:

Keep it casual and direct

Pro-Tip: Be straightforward!
Say something simple like, “I've had a great time today, would you be interested in getting together again sometime?" It's direct, clear, and doesn't require overthinking.

Suggest something low-pressure
Instead of committing to a grand gesture, suggest coffee, a walk, or an event. For example, “Would you be interested in grabbing a coffee sometime this week?” This feels more laid-back and allows the person to say yes without feeling overwhelmed.


Look for natural openings
If you're enjoying a conversation, there’s no need to wait for some “magical" moment. There is no “right” timing. The best time is often when it feels natural!

What’s really going on:

You’re overthinking it
You’re making it seem more complicated than it is, worrying about the perfect words or the “right" way to ask.


You’re worried about coming on too strong
You might feel like you're being too forward, especially if you're not sure if they feel the same way.




You’re unsure of the right timing
You’re not sure when is the “right” time to ask. Is it during the date? after the date?