Have you ever sat across from someone on a first date, wondering if there’s a magic trick that makes them think, “I can’t wait to see her again”? I’ve been there—sometimes on a wobbly café stool, other times at a noisy bar where we both had to shout over the music.
Between my own comedic dating misadventures and the countless stories I’ve gathered from friends, I’ve learned that there’s no single perfect formula. But there are a few moves that, combined, tend to spark genuine connection and leave him craving a second round.
Here on Never Liked It Anyway, we know the value of fresh starts—so let’s dive in and see how you can make the most of your next first date, without overthinking every tiny detail.
1. Show genuine curiosity, not an interrogation
I get it: you want to learn about him. But instead of firing off questions like a detective on a deadline, aim for curiosity that feels warm and natural. When I ask, “What made you decide to move to this city?” or “What’s been the highlight of your week?” I’m giving him room to tell a story—rather than grilling him on every detail of his past.
It’s all about letting the conversation flow. Sometimes, I’ll share a brief anecdote so it feels more like a give-and-take. For instance, I might say, “I tried a salsa class last month and ended up stepping on my teacher’s foot, twice!”
Then I’ll segue into asking if he’s ever dabbled in salsa or tried an activity outside his comfort zone. By showing genuine interest, we create a space where he feels comfortable opening up.
Brené Brown once said, “Vulnerability is the birthplace of love, belonging, joy, courage, empathy, and creativity.” I keep that quote in the back of my mind, because being genuinely curious often invites small moments of vulnerability.
When we both share a snippet of ourselves, we leave the date feeling like there was a real human exchange—not just a resume rundown.
2. Keep the vibe light with humor
If you’ve caught my earlier posts, you know I’m a big fan of humor—especially heartbreak humor. But you don’t need to be a stand-up comic to keep things fun. Sometimes, a self-deprecating joke about our own clumsiness or an amusing anecdote about that time our cooking experiment went up in smoke can break the ice.
I’ve found that humor can turn awkward pauses into shared laughs, especially if the setting itself is less than perfect.
Maybe the restaurant is playing bizarre background music, or your barista spelled your name “Ampersand” instead of “Amber” (true story—don’t ask). Calling out these quirks in a playful way can actually bond you both.
There’s a difference between playful teasing and overdoing it, though. Keep it light and be mindful of his reactions. If you’re not sure whether something’s funny or potentially embarrassing, I always say, skip it.
Rather than poking fun at him or diving into edgy humor on a first date, focus on making the moment enjoyable, relaxed, and filled with shared chuckles.
3. Mind your body language
Let’s be honest: the silent signals we send often speak louder than our witty quips. While I love a good conversation, I’ve learned that leaning in a bit, maintaining comfortable eye contact, and offering a genuine smile can do wonders for the overall vibe.
If you’re worried about fidgeting, try anchoring yourself. I used to tap my foot relentlessly whenever I got nervous—like a tiny rabbit hyped up on espresso. Now, I put one hand gently on my lap or rest my elbow on the table (not in an uncouth way, just lightly) to ground myself. This helps me feel—and appear—more at ease.
Also, remember to be mindful if you have your phone out. Nothing shouts “I’m bored” quite like constantly checking texts or scrolling. Give him your undivided attention. It signals respect and interest, which is far more attractive than any filter or curated photo feed.
4. Listen actively
We’ve all heard “be a good listener,” but active listening is a step above just nodding while your mind drifts off. When he’s talking about his latest project, ask a follow-up question or reflect on something he said earlier. It shows you’re truly absorbing his words, not just waiting for your turn to speak.
I once had a date who spent ten minutes describing his passion for craft beer. I’m more of a craft coffee girl, so I had zero technical knowledge about the hops or fermentation processes he was excited about.
But I found a way to connect by saying, “I love that you’re so into the artistry behind it. What’s the biggest challenge when brewing your own batch?” Even though I had no plans to set up a home-brew operation in my tiny kitchen, we connected on the excitement of trying something hands-on.
Active listening also means noticing what he’s not saying. If he seems nervous, offer reassurance. If he’s enthusiastic, match his energy. By tuning in, you show you’re not just going through date motions—you’re genuinely there with him in that moment.
5. Offer a personal anecdote
Sometimes, we’re so eager to make a good impression that we minimize our own stories. But sharing a slice of your life helps him see you as a real person with quirks, dreams, and maybe a mildly embarrassing karaoke hobby.
I keep it low-key: maybe I’ll mention the time I tried surfing and ended up with a face full of seawater. Or I’ll share how I went to a food festival in search of the perfect street tacos but ended up falling in love with a type of tofu dish I’d never heard of before.
These are small glimpses into my world that can spark new topics—especially if he’s into travel, trying new foods, or simply wants to see what lights me up.
When you open up, it also signals that you trust him enough to get a bit more personal. Susan Cain, known for her work on introversion, has noted that deeper connections often form when we move past surface-level chatter.
A short personal anecdote can be that bridge to deeper conversation, revealing common interests or simply showing your personality beyond the usual “Where do you work?” talk.
6. Show independence
Look, I believe in embracing the moment, but I also love the fact that I have my own life. On first dates, I try not to act like a chameleon, changing my entire identity to match his.
If he’s super into rock climbing and I’m terrified of heights, I’m honest about it. “I’d probably freeze the moment I looked down,” I might say. “But I admire your courage—maybe I’ll be the one cheering you on from solid ground.”
This approach shows him you have your own preferences and aren’t just morphing yourself into the “perfect” partner. Daniel Goleman, known for his work on emotional intelligence, has pointed out that healthy relationships often blossom when both parties have a strong sense of self.
Being upfront about the things you love—your passion for painting, your Saturday volunteer gig, or your tradition of brunch with friends—demonstrates that you have a fulfilling life outside of dating. That’s intriguing. It suggests that you’re not searching for someone to complete you, but rather someone to share in your ongoing adventures.
7. End on a confident note
Finally, there’s the wrap-up: that moment when the check’s been paid or the last sip of coffee is gone. While it might be tempting to linger in awkward uncertainty, I’ve found that a confident goodbye can seal the deal.
If you enjoyed his company, say so. A simple “I had a really great time getting to know you” is honest and leaves no confusion. If the spark was there, you could even suggest, “We should check out that new art exhibit sometime,” or “Next time, let’s meet somewhere with fewer mariachi trumpets blaring in the background.”
This subtle hint of a future plan plants the seed that you’re open to seeing him again—no guessing games required.
Ending on a confident note also means not dragging it out if it’s clearly time to go. We’ve all been on those dates that last too long and become a bit stale. Part of appearing confident is knowing when to exit gracefully. That balance—friendly, honest, and self-assured—makes you memorable and sets the stage for a follow-up text or call.
Final thoughts
There’s no single trick that guarantees a second date, but these seven strategies—showing genuine curiosity, keeping the humor alive, being mindful of your body language, listening actively, sharing a personal anecdote, owning your independence, and wrapping things up with confidence—can create a spark that lingers.
I’ve discovered that focusing on authentic interaction instead of striving for perfection takes the pressure off and makes the date more enjoyable for both of you.
If you’re still healing from a breakup, remember that a fresh start—whether it’s selling an old ring on Never Liked It Anyway or giving someone new a chance—can be liberating. Sometimes heartbreak is the funniest, strangest teacher, gently nudging us into more fulfilling experiences.
So go ahead, have fun, and trust that the right person will appreciate the real you. And who knows, you might walk away with plans for a second date already penciled into your calendar.
