Confidence, Consent, and Connection in Offline Dating
We’ve gotten so used to dating apps that trying to ask someone out in person can feel antiquated, like when you’re at your parents house and hear the landline ring.
It makes sense, in a way. Asking someone out IRL is much more vulnerable and exposed than from behind the protection of a screen. But also…it’s essentially a novelty these days, so it’s more likely to make the person who’s taking that leap of faith stand out. Plus, not everyone wants to rely on algorithms to find connection. So what gets in the way?
In the therapy room (virtual or otherwise) with clients, I’ve seen dating patterns come up in many different ways, but they usually revolve around a singular theme: people are interested in building real-world romantic connections, but they’re afraid of looking awkward, getting rejected, or coming across as a creep. Nobody wants to be the butt of the joke in the group chat.
While this is 100% completely valid (and human), it’s also not necessarily a great reason to not ask someone out in person. Approaching someone you’re interested in might always be a little scary, but as Glennon Doyle says, we can do hard things.
And the more you practice it, the more natural it feels. Let’s break down some tips on asking someone out in person, without being pushy, cheesy, or creepy.
Redefining Confidence
Most people assume that the ability to flirt or initiate a conversation is all about confidence and that you either have it or you don’t. But confidence, in the therapeutic sense, is more like a muscle than a trait. You don’t need to feel perfectly self-assured to take action. You just need to trust that you can handle what happens next.
Confidence in dating starts long before you’re face-to-face with someone you’re interested in. It’s how you feel about yourself when nobody else is around. It’s whether you believe you’re someone worth getting to know. And it’s whether you can extend kindness to yourself regardless of how the conversation goes.
How to Ask Someone Out In Person Without Making It Weird
It often comes up in therapy how people want to talk to someone they’re interested in, but they’re afraid of it being weird. Or feeling weird. Or making the other person feel weird.
I believe that there’s really no one right way to go about it, but there are a few general rules of thumb that can make this kind of interaction more natural and less weird.
- Start with body language.
Before saying anything, look for subtle cues: eye contact, a returned smile, an open posture. If they glance away or look uncomfortable, it’s probably not the moment to initiate. - Keep it low pressure.
A casual comment or light compliment can go a long way. “Hey, I just had to say, that’s a great jacket,” or “I’ve seen you at this class before, right?” is more effective (and respectful) than a grand gesture or pickup line. - Stages are your friend.
For people you run into regularly (maybe the gym or your regular coffee shop) and you think you might have some chemistry, strike up conversations in pieces. This means you don’t have to ask them out the first moment you think about it. Start with just a benign comment and then circle back later on or another day. This helps relieve the pressure you might feel and builds trust between you. - Have an exit strategy.
If it goes well, great. If it doesn’t, you still get to feel proud of yourself for putting yourself out there.
People often respond more positively than we expect, especially when they can tell that we’re being genuine and not performative.
What If It’s Someone You Already Know?
Maybe you’re part of the same running group. Or you work together. Or you’ve been going to the same pottery class for months and just started having one-on-one conversations after class.
These are a bit trickier because the stakes feel higher. If it doesn’t go well, you might “ruin” the group dynamic, or feel awkward being around them afterward.
Because these situations are more complicated, they deserve a bit more of your time and intention. Make sure you build rapport first. Look for mutual signs of interest. Are they lingering to talk? Initiating meetups outside the group? Laughing a little harder at your jokes? (I mean, you’re definitely funny, but are you that funny?)
If and when you do say something, keep it light but clear. Something like this could work: “Hey, I’ve had a really good time talking to you. Would you be open to grabbing a drink sometime, just the two of us?”
That way, they can say yes or no without pressure, and the door stays open for the friendship to continue if they’re not feeling it the same way you are.
What If You Get Rejected?
Getting rejected will almost always sting at least a little bit, but most of the time, that’s where the pain ends. If you just met someone and they said “no” when you asked them out, do you think you’ll still be thinking about them in a week’s time?
Plus, rejection does not equal a big fat “F” on your dating report card. Without sounding like we’re trying to find the silver lining in every bad situation (I’m not about that toxic positivity), there actually are some good things that can come from a rejection:
- You’re practicing being vulnerable.
Rejection helps you build tolerance for uncertainty, awkwardness, and emotional risk, which are all necessary ingredients in real connection. - It gives you space for self-reflection.
For example, was I actually interested in them or was I just interested in being chosen? And one step further, why was I interested in them? Was it how they looked or was there something about their humor, their mannerisms, or their outlook on life that intrigued me? - Resilience grows confidence.
Confidence doesn’t come from things always going your way, but from surviving (and thriving) when they don’t. Each time you get rejected and stay grounded in your self-worth, you reinforce a deeper truth: your value isn’t determined by someone else’s response.
And let’s not forget that rejection doesn’t necessarily mean you did something wrong or there’s something wrong with you. It just means someone wasn’t on the same page that you were, and there are a million reasons why that could be.
You can be kind, confident, and respectful and still not get the response you want. That doesn’t make you less worthy or the effort to ask them out less valuable. What I encourage clients to do is focus on the process, not the outcome. Did you take a real chance? Were you honest? Did you read the cues?
If so, you succeeded, even if you’re not running to tell your friends about what happened.
Slow It Down
When you’re drawn to someone, it’s easy to get excited, move quickly, and throw yourself into whatever it’s turning into. That sense of urgency can be intense and all-consuming, especially if dating has felt discouraging in the past or if you’re someone who tends to overanalyze every minute interaction.
But here’s what I’ve seen over and over again: the early stage of a connection is often where the most meaningful insight happens. It’s where you notice how your energy feels around them. It’s where you start to see if there’s comfort, curiosity, shared humor, mutual interest. And those things are often much easier to feel out when you’re not rushing to define what it all means.
When you allow a connection to unfold at its own pace, without forcing a label, a next step, or a perfect moment, you create space for something more real to take shape. You also stay more connected to yourself in the process. Dating isn’t just about finding the right person. It’s about being the right person for yourself while you’re doing it.
So if you’re in that early stage of butterflies and uncertainty, try not to skip it. Don’t fast-forward to clarity or commitment just because sitting in uncertainty is uncomfortable.
Let the moment be what it is: light, flirty, and unfolding. Being fully present with someone by listening, laughing, and paying attention is often more powerful than saying the perfect thing or making a bold move.
Let connection grow before you try to name it.
Final Thoughts
In-person dating doesn’t have to be a lost skill. If you’re willing to show up with curiosity, confidence, and care, it becomes less about “shooting your shot” (although that’s obviously one piece of it) and more about making a real connection.
Not everyone will say yes. But putting yourself out there in a way that’s grounded, thoughtful, and respectful is something to be proud of.
And if this still feels hard, you’re not alone. These are the exact kinds of patterns and blocks I help clients work through in therapy.
Want to Build More Confidence in Dating?
At LightLine Therapy, we work with people who are thoughtful, self-aware, and tired of dating that feels like an interview. If you want to feel more confident in yourself and more connected to the people you meet, we can help.
Book a free consultation to get started.
FAQs
1. How can therapy for dating help me?
Therapy for relationships and dating is so much more than a place to vent about bad dates. It’s an intentional space to shine a spotlight on the patterns that drive your choices, test new ways of relating, and build the emotional resilience required for a healthy partnership.
This usually starts by mapping your attachment style and early relationship models, because those storylines decide who feels “magnetic” to you long before your conscious brain weighs in.
For example, if you grew up learning that love equals caretaking, you may keep choosing partners who need rescuing. If praise was conditional on achievement, you might pull away from anyone who seems genuinely available, since availability feels undeserved. Naming these scripts helps you better understand why you feel the way you do towards other people and yourself when you’re with those people.
Next comes emotional regulation. Dating surfaces a full spectrum of feelings: excitement, hope, insecurity, rejection, desire. Therapy teaches you to track those sensations in real time, instead of reacting on autopilot or suppressing them until they leak out as anxiety. When you can ride the wave of uncertainty without losing your center, you show up clearer, calmer, and more “you” on every date. That authenticity becomes its own filter. People who like the real you draw closer, and the ones who prefer a curated version exit early, saving everyone time.
2. Is it okay to ask someone out in a shared space, like work or a club?
It depends on the context. If it’s a space you’re in regularly, like your workplace or a tight-knit community, make sure you’re especially thoughtful. If it doesn’t work out, the dynamic can shift. But in more casual or occasional spaces, like a sports team, meetup, or social club, respectful and low-pressure approaches are usually more accepted, as long as you keep the approach on the tame side.
3. How do I know if someone is actually interested in me, or just being friendly?
This can be such a frustrating dating dilemma. And of course, the answer to this is as frustrating as the situation itself: it depends.
That said, there are usually clues if you look in the right places. Someone who’s interested will often make consistent eye contact, find small ways to continue the conversation, or subtly create opportunities to spend time with you. They might linger, initiate, or respond warmly when you’re around. Friendly people can absolutely be warm and kind, but interest often has a different kind of attention behind it. If you’re not sure, pay attention to patterns over time, not just a single moment.
4. Why does asking someone out feel so high-stakes, even when it’s casual?
Romantic vulnerability is often tied to deeper fears, usually of rejection, unworthiness, or not being “enough” for other people (or maybe being “too much” for other people). Even a simple ask can trigger old narratives: What if they don’t like me? What does that say about me? The important thing is to make sense of what we make of the other person’s response. It’s about what we make it mean. That’s why we have to ground ourselves in our own value before putting ourselves out there. The goal is to remember that you can feel nervous and still follow through.
