man and woman sitting on water during daytime

How To Genuinely Connect With Anyone On A Date

When I approached my last girlfriend at a Starbucks, I didn’t expect it to go anywhere. We had very little in common: contrasting interests, fields of work, upbringing, lifestyles.

We even spoke different languages. We switched back and forth with Google translate just to fully understand each other.

But I had a “template” flow of interaction that helped me genuinely connect with anyone I’m talking to.

And through this interaction, we realized we actually had a “spark.” It didn’t show immediately, of course. But without this template, we would’ve just been two strangers who chatted over coffee and went our separate ways — never knowing we could’ve fallen in love.

It’s easier to connect with someone on a date and have an amazing time when the interaction flows a certain way.

Have a 3-Location Plan Ready

An hour after talking about the few things we liked in common (like Avicii and sisig), I knew I had to stop our conversation. If a talk between two very different people went any longer, they’d reach the point of awkward silences and dry topics.

In the past, I would’ve simply made a graceful exit. Or, since she’s pretty attractive, I would’ve asked for her phone number.

Instead, I switched locations.

“So, have you tried this restaurant in Upper Session? The one with the live band at 6?” I asked.

“Not yet,” she said.

I looked at her, shocked. “They have the best sisig in town.”

“The best, huh?”

“Uh-huh. And one of their bands plays cultural music. Would you like to see it together?”

In my experience, going from one location to another — when done well —significantly increases the feeling of closeness. Like those cliche movie lines;

“I feel like I’ve known you forever. Even if we’ve just met.”

The closer you feel, the more at ease you become. And your best selves come out more naturally.

Now, I don’t always go to 3 different locations during a date. It depends on how the date is going. But I always have a 3-location-plan ready.

Location 1: Introduction

Someplace we can have an easy conversation. Preferably somewhere cheap and serves alcohol. Low pressure. Like a laid-back bar or a late-night cafe. The getting-to-know and getting-comfortable phases happen here.

But don’t ask the usual questions. Probe on Conversation Themes instead (see below). I also perform one or two Games here for fun (also see below).

Location 2: Movement

In one of our conversations, she mentioned she never liked wine. I asked the type of wines she’s tasted. And though she couldn’t remember their names, I realized which kind may or may not suit her tastes.

“So you’re into dark and pure brews with coffee and beer. But you’re a sweet tooth with everything else?” I asked.

“Yes! I especially like sweet or fruity flavors,” she said.

“I think I know exactly the kind of wine for you. Would you like to give it a try?”

“They have it here?”

“Nope. But we can buy it at a store. And there’s this spot where you can see the mountain lights. It’s just nearby. We can stroll over and drink it there.”

“Let’s do that!”

The idea is to give your bodies the opportunity to communicate. So I always opt for a stroll (or a club, if my date is into dancing or EDM) after an hour or two of sitting and talking. It gives contrast to the date. And movement helps you feel each other’s vibe better.

Connecting with someone isn’t limited to talking.

I’ve experienced a date where we conversed non-stop for hours, jumping from one cafe to the next. Just talking. And that’s fine if you’re enjoying it. But we can amplify the energy and fun-ness of a date when we switch to a place we can move our body around — together.

That’s also why I don’t recommend the usual “date idea” stuff like hiking, biking, etc. unless you’re both hardcore mountaineers/bikers or you’ve gone out on more than 6 dates. These things focus too much on the activity, not on your dynamic together.

Location 3: Intimate conversation

During the stroll, we listened to each other’s “guilty pleasure playlist” through my earphone splitter. We may have done an awkward dance number on the streets too. But we were laughing too hard, so I doubt it looked anything like dancing.

We reached the mountain lights spot and we opened the wine. We drank with paper cups bought from a nearby 7–11. Just as I hoped, she liked it. The spot is pretty quiet, but with just enough lights to give it a safe and serene atmosphere.

Over wine and a view of the mountains, blinking with city lights, we talked about love, dreams, and life. It was a great space to talk about intimate and important things.

Then we shared our first kiss.

Conversation Themes

Years ago, I used to have a memorized list of conversation topics. I used it when the small talk is getting tedious. But they made me focus too much on what I memorized. And it’s trying too hard.

So I focused on Topic Themes instead. I’d usually go for:

a. What drives your date — I found that talking about work or hobbies (even if you have similar fields or interests) is good for small talk. But not much when really getting to know the person.

Instead, probe how or why they choose to do their work or hobbies. Try to see where their drive and desire are coming from. And engage them there.

b. What exhilarates your date — don’t make the date too serious. Probe at fun things too. My usual go-to is music. Most people are passionate about certain music.

When the time is right, I’d ask my date for her “top guilty-pleasure song.” And we’d listen to it together. (I often bring my earphone splitter). This leads to swapping weird but great music.

It’s a great way to know the person’s vibe. And it can be a jump-off for a dance club, a quick karaoke with drinks, or an awkward dance number on the streets.


Never underestimate the activities you did for fun at age 10. They just might brighten your dates now.

Think of Games as an add-on to your conversation. Like intermissions or bridges to deeper connection. You can whip them out to break the ice, put on a certain mood (intellectual, playful, flirty, etc.), or even increase physical intimacy.

I especially love the 5 Questions Bet.

You: To decide who gets our coffee (alternately, you can bet a beer, a hand massage, a phone number, or anything small), let’s play a game. It’s more fun that way.

Your date: Okay.

You: Have you heard of the 5 Questions Bet? I ask you 5 questions: You answer all of them incorrectly — and you win. If you answer even one question correctly, you lose. The questions are pretty simple.

Your date: No, I haven’t! Let’s try it!

You: Alright! And you have to make your answer as incorrect and surreal as possible. So we know it’s wrong. If it’s close to the truth, you still lose. Fair?

Your date: Sure!

You: Great! First question, what’s your name?

Your date: Donald Trump.

You: Nice! What city are we in?

Your date: Rome

You: Doing well! What’s the name of this cafe (or bar, resto, whatever)?

Your date: Starbucks.

You: You’re pretty good at this! (Pause for a bit, look down, touch your face, and look a bit confused). Wait, how many questions have I asked already?

Your date: (If they answer “three” or even “four” — you win. If they figure out what you’re doing and answer with a different number, proceed to the 5th question)

You: (Shocked and impressed) Wow, you really got me there! You’ve played this game before, haven’t you?

Your date: No!

You: Gotcha. (Pause). Thanks for the drink.

It’s an old game I got from Neil Strauss, a NY Times best-selling author. Some people might say his work on dating is toxic. But they hold lots of material you can use to make your date more fun.

You’ll have to practice this kind of stuff first though. If you forget certain steps, you’ll just ruin them. So try it on your friends first.

You can also play personality-based card games. Like Never Have I Ever. You don’t even need to bring an actual deck of cards. Just download an app. Though I’d recommend these on the 2nd or 3rd dates when you’ve established more trust and rapport. So you can play it honestly. Which makes it more fun and, in my experience, hilariously shocking.

How many “sparks” have you missed, just because you thought you were incompatible?

My last girlfriend and I were very different people. But with the template above, I learned we were actually in the same phase in life.

She had just quit her job to travel abroad. And I had just quit my job to move to a different city. We both uprooted ourselves to go after what we want.

In my experience, being in the same phase in life affects a relationship more than we think.

Dating involves luck, sure. But it relies more on the people doing it. We can always direct our experiences. Even if we don’t find “The One,” and even if things don’t work out in the end — we can have an unexpectedly amazing, fun, and memorable time.

This article was originally published on PS I Love You. Relationships Now.