After going on hundreds of first dates and guiding dozens of long-term clients as a dating coach, I have found several first-date tips that you will find especially useful, such as:
- How to dress normally without driving yourself crazy
- How to deal with pre-date anxiety
- How to avoid awkward silences on a date
Today, you'll learn all that, plus quite a bit more.
Enjoy, and let me know what you think in the comments,
1. Dressing for a first date
When it comes to dressing for a first date, there are three golden rules to keep in mind - CCP:
- Casual: You don't want to look like you've just rolled out of bed, but you don't want to appear dressed for a Monday morning board meeting.
- Comfort: Choose an outfit that you feel comfortable in. This isn't the time to break in those new high heels or tight jeans. If it's chilly or drizzling, wear an extra warm coat. You don't want to be caught shivering, giving your date the impression that you're nervous.
- Personality: Your outfit should reflect who you are. Whether you're going for the bad boy look with a leather jacket, ripped jeans, and boots or the geeky look with a smart casual blazer, graphic tee, and slim-fit chinos, let your personality shine through.
Let's go through some examples:
For a summer date, consider a dark blue polo, blue shorts, white sneakers, and a biker's chain bracelet. (Pictured below.)
Wear leather boots, black jeans, a white T-shirt, and a leather jacket in the spring. (Pictured below.)
Keep the boots and jeans during the winter, but switch to a sweater and coat. (Pictured below.)
As a guy, I can't give fashion advice to the girls here, but these Reddit posts should help you: What are some of your favorite first-date outfits? And What’s your go-to first date outfit/outfit formula?
Here are some additional tips:
- Show off your muscles by wearing well-fitting clothing
- White sneakers can look great, but only if they're spotless. Pay special attention to the laces.
- Add a touch of style with cool accessories like a watch, ring, bracelets, or earrings. (Read: How to look more masculine.)
- Believe it or not, girls do notice your nails. Keep them trimmed and clean.put together
- Iron your clothes. I know it's a pain, but it'll make you look put-together.
- Boots can add a few extra inches to your height and give you a more masculine look. I've received many compliments on my boots, and I'm already 190cm tall.
But avoid cowboy or work-style boots...
Bottom line: Look good, feel good, and make a great first impression.
2. Be the planner
Man or woman. If you want to date, you have to plan it out. Please don’t leave it up to chance. This is your love life.
Let me repeat that, just in bold:
Please don’t leave it up to chance. This is your love life.
3. Pre-planning your first date
In my opinion, the purpose of texting before a first date is logistics, i.e., setting up the date. Getting to know someone should only be done in person, not over text messages.
That's why I recommend my coaching clients to plan their first date within a week of starting the conversation.
During this 'pre-planning' week, practice these helpful pro tips:
- We're adults now, which means life sucks; uh, I mean, life is busy. So, it's perfectly fine to block off a specific time later in the week for a date. There is no need to force it into your already busy schedule. (I call this the 7-Day FriendLag Rule.
- If your date involves food, consider potential allergies - although, as a dating coach, I usually advise my students against dinner dates for the first meet-up.
- Bars tend to be overcrowded and noisy during the weekends (pictured below), so look for a weekday date for a more calm, intimate setting.
- Be aware of your date's work schedule to know when to suggest convenient times to meet up. But as a general rule, the best time to start a first date is around 6 p.m.
- Keep an eye on the weather forecast. If it’s going to rain, bring an ‘XL umbrella’ just in case your date forgets theirs.
- If you're planning a date outdoors (e.g., park, lake, walk), suggest they bring sunscreen if it's sunny or an extra heavy coat if it's chilly.
- Use Google Maps to research your date venue to look for live music events, public reviews, and when it’s least busy.
4. Pick the Best First Date Ideas
Look at my complete guide, "My Top 57 First Date Ideas That Always Work (As a Dating Coach)," for an extensive list of first date venues and over 100 pictures.
For a quick snapshot, though, the best first date spots come down to these three classics:
And some walking around lovely areas of the city.
That’s it. No crazy, expensive clubs or safari tours to impress your date.
Here's a little secret:
First dates aren't really about getting to know each other.
- If it's casual sex you're after, getting to know each other is pointless.
- And if you're thinking long-term, save the deep talks for later dates.
For now, it's about ensuring you enjoy each other's company and, well… confirming that neither of you is a serial killer!
5. First Date Venue Checklist
Now that you’ve picked several venues use this cheat sheet to pick out your top 3 options:
- Venue Lighting: Does it set the right mood with a cozy glow?
- Age Appropriateness: Is it a hotspot for your age group, or will you feel like you’ve time-traveled to the Middle Ages?
- Affordability: Is it within your budgets?
- Reservations: Do you need to call ahead?
- Fun Factor: Is it fun without trying too hard or paying?
- Menu Options: Is there food available? Is the food half-decent?
- Operating Hours: What are the closing times on weekdays and weekends? And double-check for public holidays.
- Noise Level: Can you chat, or do you have to shout?
- Vibe: What's the feel of the place?
- Crowd: Is it packed or roomy?
- Dress Code: Is everyone all dressed up, or can you dress casually?
- Comfort: Is it a place where you can lounge for hours, or will you feel like you’re sitting on a bed of nails after an hour?
- Common Interests: Is it something you’d both be into?
- Reviews: What do recent reviews say? Have any of your friends been on a date there?
- Deals: Are there any happy hours or two-for-ones you should know about?
Look at my first date venue guide for everything else you’ll need to know.
6. Memorize Your Date Plan
To keep your first date even smoother and stress-free, memorize your game plan.
- Pen and paper. There's something about pen on paper that cements details in your memory. Plus, it's a great backup. (Pictured Below.)
- Use Google Keep and sync it with your smartwatch. This way, you can sneak a peek at your plan without the obvious phone check. (Screenshot below.)
- Familiarize yourself with the area. Rehearse the walk to each venue, scout out the best seating spots, and (very) optimistically plan the smoothest route back to your place.
Now you can focus on the date without thinking about directions or when this or that bar will be closed.
7. Confirming the first date over text
The day of your first date has finally come by; how do you confirm the date?
Lots of fun ways!
- Hi [your date’s name], this is [your name] secretary confirming our date for tonight at [time of date].
- I’m finishing up [cool project]. See you tonight!
- It looks like it’ll be raining later, don’t forget your umbrella 😉
- I’ll be 10 minutes late; some work just popped up.
8. Managing First Date Stress
Here are my top 10 tips for managing first date stress:
- Even after hundreds of dates, my heart still dances before I meet my date. Even the most seasoned public speakers get butterflies before they get on stage. It's a universal human feeling. So, make friends with it and learn to manage it - not eliminate it.
- Even if your date seems cool, they’re probably just as nervous.
- Think 'playdate,' not 'date.' Remember when you were a kid, and you invited a friend over? It was about fun, not a romantic interrogation test.
- Don't get caught up in qualifying your worth to your date. Flip the script. Your date should be working to impress you and gain your attention, not vice versa.
- Hit the gym a few hours before the date. Deadlifts are a great stress reliever. Running is great, too, but nothing beats the reset button of lifting weights.
- Know your date plan and the route to each venue like the back of your hand. Less to worry about means more focus on the fun.
- Give yourself a pep talk. Tell yourself it's okay to be nervous; you'll improve with time and practice.
- Try some rejection therapy before the date. It's a great way to build resilience. (Check this out.)
- Practice the Wim Hof Breathing Method. It's a game-changer. (See below.) And skip the meditation apps; they make you more nervous.
- Avoid alcohol: Here's a little story from my experience. As a bisexual guy, I've dated both men and women. But the very first time I went out with a guy, I was scared shitless. I thought a little vodka might take the edge off. But when I met him, he wasn't happy that I'd been drinking. He told me about a previous date who'd overdrunk and ended up acting strange. I assured him I'd only had a little to calm my nerves, and he was okay. But the lesson was clear: alcohol isn't the answer to pre-date jitters. It's better to face the nerves head-on. Trust me on this one.
9. Arriving late to the first date
Here are the rules:
- If you're running late, a quick, no-apologizing message will do. Just a simple heads up like, "Hey [name], got caught up with [issue], I'll be about 15 minutes late."
- If you'll be over 30 minutes late, apologize, suggest rescheduling to another day, or ask if they're okay with pushing the time back a bit.
- If your date tells you they're running 10-15 minutes behind, a chill response like "Sure, no worries" is good.
- If they're considerably late but offer a sincere apology and a solid reason, it's up to you—stick with the plan (“Looks like the first round's on you then!”) or suggest meeting another day. Feel free to cancel the date if they're late without a decent explanation or apology.
10. Meeting your date for the first time
- The best place to meet is somewhere safe and well-lit, ideally near a recognizable landmark. This way, you're easy to find, and there's no need to comb through a crowded bar to find each other.
- Confirm this spot over text with a picture and Google Maps location pin for clarity. (Pictured below.)
Learn from my mistakes:
When I first moved to Brussels, I asked a date (a charming single mom) to meet at "Pl. De Brouckère," a busy area. I didn't realize it's a whole area, not a specific meeting spot. We ended up searching for each other for several awkward minutes. Despite the initial hiccup, the date was fun, with lots of making out! (Unfortunately, I screwed up at the end, so there was no second date. But that's a story for another time.)
- If your date is driving, try your best to save a parking spot for them. It's a small, thoughtful gesture.
- When you first meet, flash a warm, genuine smile. We all look less ugly when we're happy and relaxed. (Okay, some people are naturally gorgeous, but a smile works wonders for the rest of our zombie faces!)
- If you're in a country where it's customary to greet with a kiss on the cheek, go ahead and do that.
- Then, a simple "Hi [name], [simple compliment], nice to meet you" is perfect. Compliment something about their appearance, like their shirt. Show your attraction, but not overly friendly or sexual.
- Let them know you've picked out a cute bar nearby that you'd love to take them to.
- As you walk, chat about random things: “How was your date? Was it easy to get here?” You're establishing that you're (mostly) normal, and the date will be enjoyable.
Buying flowers is an over-investment these days.
But here's a fun, casual alternative I like to do: pick a small branch or flower from a nearby plant or bush and offer it as ‘your flower’ with a cheeky smile.
11. Improvise during the date
You’ve written it all down, but let’s say they change their plans, your date venues are closed, or there’s a football game, and all the bars are too loud.
Or, let’s say you forgot to plan (I’ve done that).
What can you do?
When I met the bisexual Brazilian in Portugal, I didn’t have much of a plan, and the coffee shop I thought we’d visit was closed.
So, I improvised.
We got ice cream, rented an electric moped, chilled on the beach, and then I took her to my place.
If you’re fun, then anything is fun.
When my boyfriend and I were waiting for a train a couple of months ago, we didn’t just sit around on our phones. We went out to a nearby cornfield and jumped around like weirdos.
Here’s another made-up example.
Let’s say you’re stuck having a date at a library. Well, some libraries will let you use their recording equipment, so why not write a song together?
- Think about what ideas you want to incorporate into the song
- Come up with a tune
- Make up the chorus
- Write the verses of the song
- Name the song
- Record it
And while you are doing this, you’ll have plenty of things to discuss.
Or, you could play hide and seek around the library shelves like I did with my boyfriend:
Or pretend like you’re shooting each other with umbrellas...
12. First Date Etiquette
Simple first date etiquette rules:
- Be cool with the staff. It's best if you’ve tipped in the past; they’ll make your life easier in the long run as you bring more dates to the same venue. Plus, they’ll give you a big smile when you walk in, signaling social proof.
- Avoid your phone. (If your date looks at their phone periodically, you do the same. If it gets bad, ask them nicely to put it away or end the date.)
- Say please, thank you, etc.
- Avoid using curse words, even when trying to be dramatic.
- Start by sitting opposite each other in your first venue, then switch to sitting at a 90-degree angle to increase intimacy in the second venue.
- Have up to 3 drinks.
- If you’re feeling extra nervous, break the 4th wall and tell them that you haven’t gone on a date in a while, so you’ve been feeling extra nervous.
Get my other 'never do this on a date' list: What Not To (Ever) Do On A First Date: 27 Examples
13. How to Drink on a First Date
If alcohol is a deal breaker for you or your partner, I’m not saying you should meet each other in the first place, but there’s a good chance this relationship won’t work out.
Next, even if neither of you wants to drink, going to a bar is still a solid first date venue. I love the people, music, dancing, and the atmosphere.
Also, there are plenty of mocktails (the non-alcoholic versions of cocktails) to try Virgin Mojitos, Virgin Mary, or Mojitos.
14. Paying for the first date
The best way to deal with the big question of who will pay is by simply saying, “The first round is on me,” which means your date will pay for the second round.
Easy and simple.
However, if your date is adamant about paying, don’t force it. Let them do what they like.
15. What to talk about on a first date
Having a drink or two helps the conversation flow, but beyond that, here are two tips about taking on a first date:
Cool Photo Gallery
Prepare a photo gallery around a recent adventure or exciting project you can share on a date. Make sure you're not oversharing, but leave room to subtly show off a fun, social life.
For example, if you've been on a two-week motorcycle trip with friends, make that your 'date album.' It's a perfect way to showcase your exciting life and sociability and kick-start a conversation about travels you both have experienced.
For a playful twist, pick your favorite photo from your adventures and concoct a funny, exaggerated story about it.
For example, you could say, "This shot was taken during my winter holiday in Greece."
(Which it was. And by the way, Greece is a beautiful country with kind people. I will visit again.)
Then, with a wink, you say:
"The real story behind this photo? After my three friends were overpowered, I single-handedly fended off a band of pirates. Fortunately, a storm blew in, allowing us to make a daring escape to an uninhabited island, where we lived off the land for five years. We were finally rescued when a passing commercial pilot spotted our smoke signals."
A date is more than just a meeting; it's an escape from the monotonous routine of everyday life. So, let your playful side shine through.
Childhood and Life
No traumatic stuff - we all have those stories, but basic open-ended questions to get to know each other:
- Where were you born? Could you show me on Google Maps? Do you have any funny pictures to share?
- What did you want to be growing up? How’s that coming along?
- What kind of kid were you growing up? How did you change?
- Who was your childhood crush? What did you like about them?
- what would you do for the rest of your life if you won the lottery today?
I could go on for hours, but that’s enough for now. If you’d like to know more, read:
16. Compliments on a first date
When you first met your date, you gave a nice compliment, and that’s good.
But throughout the date, you’ll have to give more romantic compliments to convey your desire to avoid falling into the friend zone. Sexual compliments are not 'bad' during a date. Just stay calibrated, and don’t be vulgar.
17. How to tell if your first date is going well
If your date is going any of the following, your date is going well:
- Buys you a drink
- Laughs at your jokes - even the bad ones
- Blushes and gives you mesmer eyes
- Playfully teases you and calls you a jerk
- Talks a lot
- Asks you lots of questions
- Has lots of open body language
For a more in-depth article on all the signs that a girl likes you - including during the date, read Falling in Love: 124 Signs to Tell if a Girl Likes You 
18. Kissing on the first date
I got an article about first date kissing, but in short:
Wait until you’ve been chatting for an hour or two, sit beside each other or at a 90-degree angle, look for signs that they’d like to kiss you, lean in while gently holding onto their side or back, and kiss lightly.
For tips on kissing a short girl, read this guide.
19. How to find the bathroom on a date
Most of the time, you’ll find the bathrooms by going down a staircase.
Once you get down the staircase, look closely because some ‘male’ or ‘female’ bathroom signs can be hard to read.
20. Ending The Date
Generally, don’t let your first date go on for more than 3 hours.
If it's going well, you don't need to go overtime. You’ll meet again.
It’s been a lovely evening, especially [callback joke]. I’d love to meet again, but I gotta get going. Have a nice evening!
If you chickened out earlier, you can use this opportunity to go in for the kiss as you drop them off (pictured below), or you can go for a hug.
If it hasn’t been going well and you want to end the date, say this:
"I wanted to let you know that I enjoyed meeting you, but I am not feeling the connection that I am looking for. I wish you all the best. Take care!"
For more examples and my guide to rejecting others, read: 59 Moves: How To Tell A Someone You’re Not Interested And Reject a Guy or Girl [& Countless Examples] 
21. Taking your date home
If your date is really into you, like lots of making out, and it's pretty clear they wouldn't mind heading back to your place (and you're feeling the same), there's no need to play the 'hard-to-get' game. Just stay calm and casually suggest showing them something fun at your place, like your new Fender guitar. If they agree, then it's off to your place.
22. Online First Date Tips
Online dates are not recommended, but if you have autism or for whatever reason you don’t have any other option, do the same thing you’d do over a regular date, just over a Zoom call, just not more than 1 hour.
After you’ve left, send them a simple text wishing them a safe trip home and a lovely evening.
Hey [name], I really enjoyed our time together. Let me know when you get home safely. Have a lovely evening!
If they text back with a nice message saying that they had a great time with you, wait till the next day and tell them that you’d love to meet again for a second date:
Hi [cute nickname], I’d love to hang out again; this time, we should visit [name of bar they mentioned].
And you move from there.
For me, read my complete guide on planning and setting a second date.
24. LGBT First Date Tips
If you’re a gay or bisexual guy reading this post, you’ll find this article super helpful: How to Get a Gay Boyfriend: 25 Tips That Work.
It’s not strictly about getting a gay boyfriend; there’s tons of helpful information in there.
But besides that, here are some LGBT dating pointers:
- Don’t treat your dating any differently than straight dating—no need to talk about LGBT subjects during the date. Don’t let being gay become who you are. I actively date as a bisexual guy and trust me; it gets boring.
- Avoid gay bars unless you’re looking to hook up. Otherwise, go for a typical bar that you like.
- Be mindful that although you may feel comfortable kissing in public, your date may still feel nervous from internalized homophobia and worried that someone from his community will see them
25. First Date Resources
- My Complete List of Best Dating, Sex & Relationship Books for Men
- Nuclear Caudillo YouTube Playlist (Episodes 1-9)
- Sex and Psychology Podcast by Dr. Justin Lehmiller
- Double Teamed Podcast with Cami and Niki (YouTube, Instagram)
- Lovers and Friends Podcast with Shan Boodram (Youtube, Instagram)
If you need personalized coaching for your dating life, feel free to send me a message below. I may not have always been the most charismatic guy, but I've figured out how to stop loneliness and build a great social life - I'm confident I can help you, too!
Please message me, let's transform your dating life.
26. Staying safe on the first date
Your chances of meeting a serial killer through online dating are slim to none, but that doesn’t mean online dating isn’t dangerous - especially since you don’t know each other.
Plus, if you’re new to dating, blowing these fears out of proportion is normal.
Here are some tips to feel and stay safe:
- Use live location on WhatsApp or Find My on iPhone to share your location with a close friend
- Always meet in public.
- Don’t get into any car.
- Start your date by saying you must leave early if your mom needs you. Making this excuse will make it easier to end the date if you aren’t comfortable.
- If they start walking, talking, or doing anything weirdly, say that you’re not feeling the chemistry and have to leave.
- Go to a bar where one of your friends works so they can keep an eye on you
- Ask a friend to silently pass by halfway through the date to make eye contact to ensure you’re doing OK.
Beyond that, check out these resources:
- Online Dating and Dating App Safety Tips | RAINN
- Online Dating Safety Tips | 8 First Date Tips for Women & Men | ADT
- 1st date safety tips? : r/hingeapp
In summary, dress impressively yet comfortably, reflecting your personality (CCP: Casual, Comfort, Personality). Plan meticulously, focusing on logistics rather than deep conversations via text. Ideal first date venues include cafes, bars, or parks, chosen for ambiance and comfort. Manage pre-date anxiety with preparation and positive self-talk, remembering that the date is about mutual enjoyment, not intense interrogation. Adhere to simple etiquette, like politeness to staff and minimizing phone use. Be adaptable, ready to improvise if plans change, and maintain a playful, positive attitude. Lastly, ensure safety and comfort for both, including choosing a familiar, public meeting place and staying alert to your date's comfort levels.