A Guide To First Dates

Men's Dating

A Guide to First Dates: Preparation & Icebreakers

Cassey Ashley Sua

Written by: Cassey Ashley Sua

Cassey Ashley Sua

Cassey blends her background in social and human behavior, along with digital marketing, seamlessly into her writing. With a versatile portfolio spanning Tourism, E-commerce, Tech, Hospitality, and Medical industries, she weaves meaningful narratives that resonate with audiences. Connecting words into sentences is her craft, but Cassey also finds joy in forming genuine connections with people from all walks of life on LinkedIn.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Reviewed by: Amber Brooks

Amber Brooks

Amber Brooks is a dating and relationship expert who has penned over 1,800 lifestyle articles in the last decade, and she still never tires of interviewing dating professionals and featuring actionable advice for singles. She has been quoted by the Washington Times, Cosmopolitan, The New York Post, and AskMen.

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A first date is a big deal — it’s that exciting first meeting where two people explore the potential sparks of a romantic relationship. It’s an opportunity to connect, share stories, and find out if you both love the same weird hobbies and Netflix shows. 

Sure, the thrill of a first date can be electrifying, but let’s be real, it often comes with a side of nerves and awkwardness as you figure out this whole “getting to know each other” thing.

Our experts aim to take the mystery out of first dates with practical tips to help you shake off those jitters.

This article will cover everything from preparation and conversation hacks to good old-fashioned etiquette. By the end, you’ll be armed with the confidence to totally rock your first date. 

Whether you’re a dating pro or just dipping your toes into the world of romance, this guide has got your back with insights to make your date memorable and fun.

Preparation | Icebreakers | How to Exit Gracefully

Preparing for a First Date

The anticipation of a first date comes with that classic combo of excitement and nerves. But don’t worry, a bit of prep can set the stage for a successful date experience. 

We will walk you through the steps to make a stellar impression and keep your cool throughout the date. 

1. Know What to Expect from the Venue

Selecting the perfect venue for your first date is all about the ambiance. You need good vibes for that first meeting.

venue first date

Our experts advise daters to choose a local spot where you can actually hear each other talk, perhaps a cozy coffee shop, a laid-back restaurant, or even a sunny park. 

Do a little recon on the place beforehand to get a feel for its vibe (maybe check out the menu). This helps avoid any awkward surprises.

Knowing the scene can ease your nerves and make you feel like the smooth operator you are when you show up.

2. Select an Outfit

Your outfit is key to making a great first impression. Pick something that screams “you” and suits the venue. 

first date tips

Comfort is everything! Go for an outfit that makes you feel like a million bucks. You need to be comfortable because confidence naturally follows.

Aim for a polished look, but don’t go overboard with too fancy attire. This is a first date, not a ballroom gala. 

You don’t have to shop for an entirely new outfit just for your date. Your attire should complement your natural style (something you should already have in your closet), not steal the spotlight.

3. Get Psyched 

Mental prep is just as important as hitting the gym. So, for your first date, bring a positive mindset and an open heart. 

get excited for your first date

Picture everything going smoothly and think about the chance to meet someone awesome… instead of stressing over what could go wrong. 

Beforehand, do things that chill you out and make you happy. Blast your favorite tunes, dive into a hobby, or even try some mindfulness techniques. 

Rolling in with a calm, positive vibe will help you enjoy the moment and genuinely connect with your date. And hey, if all else fails, at least you’ll have a good story to tell!

Conversational Icebreakers

Let’s be real—starting and maintaining a chat with someone you’re just getting to know can be tricky. The right questions and responses can make all the difference in creating a meaningful conversation.

This section will provide you with practical tips on how to break the ice and keep the conversation flowing smoothly. Whether you’re naturally talkative or more reserved, these strategies will help you navigate the initial stages of getting to know your date. 

From asking thoughtful questions and really listening (no, seriously) to sharing quirky stories and steering clear of touchy subjects, you’ll learn how to foster engaging and pleasant interactions that could lead to a genuine connection.

Ask Good Questions

Kicking things off with some thoughtful, open-ended questions can really set the stage for a great chat and successful first date. 

get to know your date

Ask about your date’s childhood, travel adventures, favorite books, life goals, or simply what they like to do on weekends. 

These kinds of questions get your date talking and sharing more about themselves. That gives you both a chance to learn about each other and bond over mutual interests. 

You might discover you both have a thing for ‘80s movies or an obsession with hiking trails. Stay present and make the conversation fun and engaging!

Respond to Their Answers

Active listening is crucial on a first date. When your date answers your questions, really tune in and engage. Nod, smile, and toss in some thoughtful follow-up comments or questions to show you’re genuinely interested. 

This should be your secret weapon for building a connection. Listening demonstrates respect and helps build that all-important rapport. Channel your inner talk show host (minus the cue cards), and you’re golden.

Tell Unique Stories

Sharing unique stories from your life can keep the conversation lively and provide insights into your perspective and your personality.

tell a personal story

Focus on anecdotes that are both interesting and relevant to what’s being discussed. Don’t go off on boring tangents about what you had for lunch.

Personal stories can make a first-date conversation more memorable and help your date get to know the real you in an authentic way. 

So, go ahead, share that hilarious mishap from your last vacation or your unexpected talent for karaoke! Keeping it real and fun is the key.

Avoid Polarizing Topics

It’s important to dodge polarizing topics and deeply personal matters on a first date. It should be like navigating a minefield – stick to the safe zones! 

Keep the convo light and upbeat to foster a comfy atmosphere. This way, both of you can relax and actually enjoy getting to know each other. After all, who wants to debate politics over coffee?

Red Flags of Bad Dates

Navigating the world of first dates can be a wild ride. While some dates might feel like you’ve just met your soulmate, others can reveal red flags faster than you can say, “Check, please.” 

Spotting these warning signs early on can save you a ton of time and emotional energy. So, let’s go over common first date red flags that can help you decide if the person is worth a second rendezvous.

The Talker

One of the biggest red flags on a date is when a person hogs the conversation like it’s a solo podcast.

first date guide

The Talker is that person who can’t stop yapping about themselves, their achievements, or their interests, without ever pausing to ask about you. 

It’s like listening to a broken record. This can make you feel like a silent audience member rather than an active participant. 

Remember, a good conversation is like a game of ping pong – it goes back and forth. If your date is not giving you a chance to volley, it might be time to swipe left (in real life).

The Negative Nelly

Another red flag is encountering a date who’s always complaining or focusing on the negative aspects of life.

avoid negativity

Meet Negative Nelly, who loves chatting about current problems, past grievances, and ongoing frustrations. 

Sure, we all have bad days, but constant negativity can really suck the fun out of your time together. Remember, positivity and optimism are important aspects of a healthy relationship.

If your date can’t seem to find the silver lining in life, maybe you should consider giving this one a pass.

Rude Behavior

Rudeness is the ultimate red flag, and it’s one you should never ignore. Whether they’re being disrespectful to you, the waitstaff, or anyone else you encounter during the date, it’s a big no-no. 

looks out for first date red flags

Rude behavior can show up as condescending remarks, dismissive comments, or just plain lack of basic manners. It’s like the universe’s way of saying, “Abort mission!” 

Such behavior often hints at deeper issues with empathy and respect, which are the bedrock of any successful relationship.

If your date is acting like they skipped the “How to be a Decent Human 101” class, it’s a clear sign they might not be your perfect match. Save yourself the trouble and opt out on rudeness!

How to End the Date 

Ending a first date can be just as nerve-wracking as starting one. Seriously, what’s the protocol here? Knowing how to wrap things up gracefully can make a lasting impression, regardless of how the date went. 

In this section, we’ll share some tips for navigating those final moments. Should you go for the kiss? How do you set expectations for future contact? And how do you leave on a positive note? 

Here is some practical advice that will make sure you end that date like a pro!

To Kiss or Not to Kiss

Deciding whether to kiss at the end of a first date can be like navigating a maze. The trick is to read the signals and trust your gut. If the date was a hit and there’s obvious chemistry, a goodnight kiss might just feel right. 

first date tips

But hey, if you’re feeling iffy or sense any hesitation, no worries! A warm hug or a genuine “thanks for a great time” can show that you’re interested while respecting each other’s comfort zones. 

Remember, dating is not a Netflix rom-com. It’s all about being real and taking it one step at a time.

Set Expectations to Talk or See Each Other Again 

Before calling it a night, it’s super helpful to set clear expectations about future communication or plans. If you had a blast and want to hang out again, just say it! 

first date tips

Something like, “I had a great time, and I’d love to do this again,” works wonders. 

If you’re not feeling a second date, be kind but honest. A simple “It was nice meeting you. Thanks for tonight” does the trick. 

Clear communication helps manage expectations and avoids any awkward misunderstandings.

Leave on a Positive Note (Even If It Went Poorly)

No matter how the date went, always aim to leave on a high note. If it wasn’t the best, you can still appreciate the effort and time spent together. 

Showing politeness and gratitude will be good for your dating karma. A gracious exit ensures both parties part ways with dignity and respect. 

first date tips

Ending things amicably can leave the door open for a possible friendship or future opportunities, even if romantic sparks weren’t flying. Plus, who knows? You might have just met your new trivia or brunch buddy!

The Bravery to Go is All You Need

The thought of a first date can be daunting and fill you with questions about where to go, what to wear, and how to keep the conversation from fizzling out. But honestly, the biggest win is just showing up. 

Taking that leap of faith and putting yourself out there can be a victory on its own. It shows you’re ready to enjoy new experiences and make connections.

Heading into a first date with an open mind is key to having a blast and maybe even finding that special spark. Ditch those rigid expectations and preconceived notions – just be present and genuinely engage with your date. 

An attitude of openness makes for real, authentic interactions, helping you appreciate your date for who they actually are, not who you think they should be. Every date is a learning experience, and even if it goes poorly, you’ll learn more about yourself and what you’re looking for in a partner.

Embrace the journey with curiosity and a positive attitude, and you’ll find that every first date turns into a rewarding adventure. Who knows? You might even have a great story to tell your friends, or at the very least, you dove into new experiences and may even make new connections.