How to Absolutely Nail a First Date

(and leave them thinking about you)

I’d like to think I’m pretty good on a first date. Either I’m not self-aware enough to know that they aren’t going well, or they are, in fact, going well, and I’m just fantastic company. I’d like to say it’s probably the latter, but there is a third possibility—one that’s embarrassing to admit: maybe I'm just very practiced.

Regardless, I wanted to share my tips with you all on how to go on a first date. I will say, there are some characters I have yet to encounter. For example, I’ve managed to avoid grabbing drinks with a douchebag or the awkward small talk with the shy guy. Still, I’ve been on quite a few first dates, so here it goes.

Here are the steps on how to successfully go on a first date:

Step 1: Plans

This is more for people who have the ability to play a more passive role in courtship. In the heterosexual context, that would traditionally be the girl; in a homosexual context, that would be me—whatever that means.

If he asks you on the date, allow him to make the plans. If he tosses the planning back on you with a noncommittal “idc anywhere” or “whatever you want,” trust me, he’s not worth your time. I’ve had enough propositions like these to know that it’s a surefire way to tell that a guy doesn’t really care and is going to drag his feet later on in the situationship—because it will most likely be a situationship with this type of guy. He’ll probably play the texting game, or he’ll be the ghosting type. Even worse, he might pull the slow fade-out known as “petering.”

Now, if you’re the person making plans, the responsibility is yours. Start by simply asking, “What days are you free?” Pretty basic. Not hard to mess up. Now that you know what days work best, you’re responsible for setting a date and time. I suggest a weekday at 8:00 p.m. This allows for a graceful exit if it’s not going so well, with the excuse of “I gotta get home. I have work tomorrow.”

And what should the plans be exactly? Drinks. Always drinks. An easy 30-minute assessment that can always go longer with another round if you all are feeling each other. Just don’t overdo it. You’re aiming for smooth socialization, not sloppy stories.

Step 2: The Meet-Up

After committing to a date and time, agree to meet there. No getting picked up by a knight in shining armor. Why? You need to have an escape route. No waiting for an Uber. No awkward rides back home. Drive yourself, bike, or wear some shoes you’re comfortable running home in.

Show up on time. Punctuality is polite. When you arrive, send a text, “I’m here.” The less emotion, the better. It adds to the air of mystery, making you more alluring to your date. Here’s the catch: don’t be the one to show up first. If they don’t show up on time, don’t judge. Take a lap around the block or browse a nearby bookstore. Now’s a good time to text your friend, saying, “If I don’t text you in 2 hours, call the police.”

After he says, “I’m here. wya?” you can say something like, “Alright, just stopped in this bookstore really quick. I’ll be there soon.” This builds the anticipation.

Step 3: Conversation

This is the hardest part since I can’t coach you through play-by-play. Luckily, I was given some advice on how to have good conversations.

Here’s the analogy: You don’t become a good chess player by memorizing thousands of lines. You become a good chess player by understanding general principles and knowing when to employ them.

You simply need to understand the basics of how to make conversation with someone. Here are my basics:

• Introductions: “Hey! Nice to meet you,” with a hug or a kiss on the cheek. Please, no handshakes.

• Start with your surroundings: “How did you hear about this bar?” “What are you drinking?” This is an easy way to start a conversation without having to rush into it. It’s dipping your toes into the water, not a cold plunge.

• Questions are key: Make sure to ask where they are from and what they do for work. Follow up with more curiosity: “I love California! What part?” or “What exactly does an accountant do day to day?” Always make sure to continue the conversation.

Here are some other questions that I love:

• “What do your parents do?”

• “Do you have siblings?”

• “What were you like in college?” If you are in college, “What were you like in high school?”

Those last two are my favorite because you can always follow it up with, “I might not have talked to you in college, but I totally would have had a crush on you.” BOOM.

Step 4: Flirting

What do I think flirting is? Subtle signals that create intrigue. Micro-expressions that tell someone you’re into them without totally giving it away.

• Laughing is the best way to flirt: Not belly laughs, but those soft chuckles where your lips stay together in a smile, and you expel air through your nostrils and make a small sound with the back of your throat. And don’t just laugh when your date says something funny; laugh at other times. People like to feel like they are funny.

• Body gestures: Lean in slightly, nod occasionally, and lightly tilt your head. Keep your hands close to theirs. This gets them eager to break that first touch.

If you’re bold and know they’re into you, you can always be straight up with how you’re feeling. After he makes you laugh, you can say, “You’re funny,” or how I like to do it—mid-laugh, slightly look away from him and say, “You’re cute.” BOOM x2.

People are hooked on the idea that a first date is a way to pitch yourself to someone. No, that’s incorrect. It’s to let someone know you’re into them. And when flirting is done correctly, your date is supposed to leave feeling like you’re into them but doesn’t know for certain. Imagine them telling their friend, “Yeah, the date went great. It was really fun. I’m not totally sure, but I think they’re into me.”

Step 5: Closing Out

The million-dollar question: who pays? Luckily, I have the million-dollar answer.

In the heterosexual context, the guy is always supposed to pay, but let’s face it, sometimes you’re broke. In the homosexual context, the guy is always supposed to pay, but which one? Also, what if neither of you is a guy?

Now, asking to split the tab? Which person is the one that makes that decision, or do you wait for the awkward situation when the bartender asks for the card, and you both look at each other like deer in headlights?

My idea: the inviter picks up the tab. If you like someone enough to ask them to go on a date, you should like them enough to be the one who pays. Full stop.

Step 6: Leaving

If you all made it to the end of the night, still totally into each other, leave it as is. Don’t drag it out with another bar or late-night burgers. And absolutely do not invite them back to your place. Don't just leave your date on a high note. Leaving them wanting more is key. This way, the person feels like they didn’t get the full experience of you—in a good way—leaving them begging for another date. If they say, “When can I see you again?” You got him.

Final Thoughts: Don’t Take My Advice

While this is a foolproof strategy to kill a first date, this isn’t the only way. The best way to act on a first date is to be yourself. Not 100% yourself—you should definitely put your best foot forward—but you should be your authentic self. If they don’t like the real you, why bother?

Also, mistakes make for good stories. Who cares if you make a social faux pas or the conversation runs dry? And yeah, maybe you should go to another bar after, or go get pizza slices and stay up till 3 a.m. That’s what makes dating so fun.

As for kissing on the first date? I’ll leave that one up to you.