If he hasn’t asked you out yet, these 4 easy moves could get things going

I’ve heard this question countless times—“How long should I wait for him to ask me out?”—and it always reminds me of a conversation I had with a friend who felt stuck.

She was excited about someone she’d been getting to know, but every day that passed without an official invitation sent her deeper into self-doubt.

Her experience got me thinking about the subtle dynamics of waiting: How do you balance patience and self-respect? When is it worth hanging on, and when should you move forward?

In my own journey studying psychology and Buddhism, I’ve discovered that waiting for someone to make a move can be both a lesson and a challenge.

On one hand, it can teach us about our own triggers, expectations, and desires. On the other hand, it can also lead to a spiral of second-guessing and anxiety.

This article will offer four important tips for navigating that uncertain period.

I’ll share a counter-intuitive perspective that might surprise you, invite you to reflect through thoughtful questions, and ultimately weave in a Buddhist principle—compassion—that will help you be kinder to yourself (and to the person you’re waiting for).

1. Recognize your own readiness

“Am I ready for a relationship right now?”

This might seem like an obvious question, yet many of us don’t pause to ask it. Instead, we focus on the other person’s timing, preferences, and readiness. But real power lies in reflecting on whether you are emotionally prepared.

Are you truly open to sharing your life, or are you looking to fill a void? Do you feel a sense of self-worth, or are you relying on someone else’s ask to validate you?

I remember a time in college when I desperately wanted a particular girl to ask me to hang out more often. Every day I waited became an exercise in self-torment: Was I not interesting enough? Why was she taking so long?

Later, I realized I hadn’t asked myself if I was ready to show up as a real partner in any relationship. In fact, I was so anxious and insecure that I probably would’ve sabotaged any real connection.

Reflective question

• “What am I truly seeking right now—a person, or a sense of worth that I could be cultivating within?”

When you turn the spotlight inward, you might discover that feeling ready isn’t solely about finding someone else to complete you. It’s about recognizing your own wholeness.

The more centered you feel, the easier it becomes to see clearly whether waiting is a natural part of a growing bond—or a sign of stagnation.

2. Pay attention to mutual interest (without over-interpreting)

One common piece of advice is to look for signs of interest—body language, consistent texting, or inside jokes. But let’s make it more nuanced. Instead of searching for daily “evidence” that he likes you, try to sense the quality of your interactions.

When you chat, does he lean in and ask about your experiences? Does he remember little details? Does he offer equal energy in conversations?

We often over-interpret crumbs of attention as a sign he’s about to make a move. I get it. We want something to hang our hopes on. But that can lead us astray.

In my experience, genuine interest isn’t just about showing up—it’s about presence. A quick text might be nice, but is there emotional curiosity and effort behind it?

Research by John and Julie Gottman highlights the importance of responding to each other’s “bids for attention” in relationships. Their findings indicate that couples who consistently turn toward these bids—small gestures seeking connection—tend to have stronger, more enduring relationships.

Conversely, ignoring or missing these bids can erode relational bonds over time.

Don’t be afraid to ask yourself:

• “Are we building a mutual connection, or am I the only one pushing?”

• “Do our conversations have depth, or are they surface level?”

If you find that you’re carrying the weight of keeping the conversation alive, consider that a gentle nudge from reality. Sometimes, the truth stings: the connection might not be as mutual as you hoped.

And sometimes, you’ll realize he’s just as involved and as nervous as you are. Observing the quality of your interactions can help you gauge whether waiting is a healthy, mutual progression or if you’re clinging to a one-sided spark.

3. Communicate your feelings (yes, you can hint—or even say it)

Here’s where a counter-intuitive perspective comes in: You don’t always need to wait for him. In many of our cultural narratives, we’re told to be patient, let him chase you, or avoid seeming “desperate.”

Yet, in reality, healthy relationships often blossom with clear communication.

According to research published in the Journal of Social and Personal Relationships, direct communication is linked to higher relationship satisfaction and stability, as it reduces misunderstandings and builds mutual trust.

If you’re wondering how long you should wait for him to ask you out, perhaps the bigger question is: What if you didn’t have to wait at all?

You don’t have to deliver a grand speech or make a dramatic gesture. Sometimes, all it takes is a genuine conversation: “Hey, I enjoy our time together. I’d love to hang out in a more intentional way—what do you think?”

A simple invitation can be refreshing and shows you value directness. It also respects your time and emotional energy, which is a key expression of self-compassion.

Of course, there’s always a risk in being direct. You could be disappointed or feel vulnerable. But remember that vulnerability is also the soil where authentic connections grow.

In my life, the most meaningful relationships—romantic or otherwise—have started with someone bravely stepping forward. If you sense a real connection, why not shift the dynamic?

Reflective question

• “Is it more empowering for me to keep waiting, or to honor my curiosity by communicating?”

Instead of fearing that you’ll appear too eager, trust that genuine connections thrive on sincerity. And if he responds poorly or avoids the topic, that too is valuable information about whether this is truly a connection worth pursuing.

4. Set a personal timeline (and be willing to adjust)

Often, we fixate on a hard rule: Two weeks and then I’m done. If he hasn’t asked me out by next month, I’ll never speak to him again. Rigid rules might give a sense of control, but life and relationships are rarely so black-and-white.

Instead, consider creating a personal timeline based on your emotional resilience rather than on arbitrary dates.

For instance, you might decide: “I’ll give this connection space for a few more weeks, as long as I’m still feeling respected and hopeful. If I start feeling consistently anxious or taken for granted, I’ll step back.”

This approach shows compassion for yourself—recognizing your emotional thresholds—while also leaving room for the unpredictable nature of human connection.

In my own past, I’ve set deadlines that were too rigid. I’d say to myself, “If they don’t text back by tomorrow, I’m out,” only to discover later that real life might have gotten in the way—a family emergency, a work crisis, or plain old nerves.

When I gave the situation room to breathe, the relationship sometimes evolved beautifully. Other times, it became clear that the person wasn’t willing to invest. Both outcomes taught me valuable lessons about respecting my own emotional capacity.

Ask yourself:

• “How do I feel when I think about waiting longer?”

• “Am I hopeful and patient, or growing resentful?”

These questions help you maintain self-awareness. If you consistently feel drained, it might be time to move on. If you feel at peace giving the connection more space, then let it unfold—without numbing your own feelings in the process.

Mindfulness perspective

Buddhism often highlights compassion—not just toward others, but also toward ourselves. When I talk about compassion with my students, they sometimes assume it means cutting others slack no matter what.

But true compassion recognizes that both parties’ needs are important. It’s a willingness to see another person’s fears or hesitations while also honoring your own emotional well-being.

What does this look like when you’re waiting for someone to ask you out? Compassion might mean understanding that the other person could be dealing with uncertainties or personal challenges. They might be shy, anxious, or simply slower to make decisions.

At the same time, self-compassion means respecting your own limits. If the waiting game becomes a source of daily anxiety, you’re allowed to step forward or step away.

By embracing compassion, you can let go of resentful thoughts—Why hasn’t he made a move yet?—and instead foster understanding. You can also gently remind yourself that no one else can determine your worth.

In the end, compassion is a balancing act that allows space for both patience and self-preservation.

Conclusion 

No one-size-fits-all rule exists for how long you should wait for him to ask you out. But by reflecting on your own readiness, paying attention to mutual interest, communicating clearly, and setting a personal timeline, you’ll make better decisions that honor your well-being.

Above all, remember the power of compassion—both for yourself and the person you’re waiting on. The ultimate goal is to cultivate genuine connection, not just compliance with some imaginary deadline.

If you decide to wait, do it consciously. If you decide to speak up, trust the strength of your authenticity. Whatever you choose, let compassion guide you toward the answer that leaves you feeling supported, empowered, and ready for what’s next.