What Not To (Ever) Do On A First Date: 27 Examples

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After going on hundreds of first dates, I've earned my fair share of first-date horror stories. 

Today, you'll get the chance to learn from my terribly awkward mistakes. 

Granted, we only learn from experience (and by that, I mean failing), but my guide should help you avoid common dating mistakes you probably had yet to think of. 

Good luck, 

Coach Colt

What Not To Do on a First Date thumbnail datingarmory.com

1. Masking a Friendly Hangout as a Date

Masking a friendly hangout as a first date is not a great way to escape the friend zone

If you’ve known each other as friends or colleagues, establish that you're not merely planning a casual, friendly hangout. 

You don't need to label it as a 'date,' but your intentions will need to be clear. 

Compliment them, tell them they look cute, and then suggest a drink.

Why a drink, you ask?

Well, it's not just about the alcohol. It's about setting the right tone. You're subtly communicating that you're interested in them romantically without having to say it outright, as known as tell me without telling me.

Coffee dates, while a good first date venue, can often be mistaken as a friendly (or friend zone) catch-up.

2. Over-pushing for the date

Persistence can get you laid, but there's a fine line between being determined and turning into a character from Dumb & Dumber (see below).

If you’ve asked her out multiple times and she’s always busy with something, wake up, brother, she’s not into you. 

We are all busy; she (or he) won’t make time for you on their schedule. 

(The only exceptions might be if they're swamped with final exams or wrapping up a major project.)

On the other hand...

Keep going if you're picking up signals that she's interested but playing hard to get. Plan your first date, approach her confidently, and ask her out. (I believe in you!)

Read: My Favorite 27 First Date Tips (As A Dating Coach)

3. Zero perceived effort

Let's get one thing straight: 

I'm not here to remind you about the basics. 

I know you're smart. (All my readers are smart!)

You know you should brush your teeth, shower, wear clean clothes, and show up on time. (For heaven's sake, avoid that bean burrito that will have you playing a 'flatulent symphony' for your date all evening.)

What I'm here to talk about is the Art of Effort

The magic that happens when you show your interest, when you put in that extra mile to win them over. It's about the sparkle in your eyes, the warmth of a friendly hug or a kiss on the cheek when you see them. It's about smelling like a dream and dressing like you mean it.

Playing Mr./Mrs. Aloof is overrated. 

Sure, you don't need a man or a woman. And yes, no one needs a partner to complete them. 

But let's be honest.

You agreed to this date because you want them. 

You're interested. So why not show it?

4. Over-High Standards

Meet Jane:

Strong independent working woman on a first date

Jane is about to embark on a first date with John. 

Meet John:

Working man before a date

Now, Jane has a particular set of expectations for John.

She's picturing him pulling up in a luxury car, taking her to a high-end restaurant, and paying for a three-course meal. She's also envisioning him in designer threads, with a high-paying job and perfect physique. And that's not all. Jane's dream guy also holds a master's degree, has no ex-wives or kids, and owns a house in an expensive neighborhood.

But wait, there's more! 

Jane's about more than just the material and status symbols.

She's also got a laundry list of behavioral and personality traits she's expecting from John. She's hoping for a charming, funny, and attentive man. She wants him to echo all her opinions, share all her interests, and be devoid of flaws or bad habits.

And heaven forbid if he's an Android user.

Now, this might seem like an extreme example, but it's to illustrate a point:

There's no such thing as a perfect partner. And guess what? You're not perfect, either. (Well, I'm nearly perfect.)

A first date at a coffee shop, where you spend less than 10 dollars, is normal and acceptable.

Here's the thing: If you're going on a date with a checklist as long as Jane's, you're setting yourself up for disappointment. Not to mention, you're putting immense pressure on your date to meet these unrealistic expectations.

5. Ghosting

Ghosting is never OK unless you’re worried for your safety or they’ve been rude (e.g., pushing for the date like a telemarketer after you’ve said no ten million times).

6. Late arrival text

Don't be late; if you are, send a simple apologetic text (but not over-apologetic) with your ETA as soon as you know and offer to reschedule for another day. 

7. Meeting in a car

Don't jump into a car to meet your date

"Come in! There's plenty of room. We'll head to the coffee shop up the street!"

I guess this one depends on how you first met, but if you don’t yet know each other, don’t meet anywhere without an ‘easy-out.’ And that means never meeting in your or their car—only in safe, public areas. 

8. Hiding your fears or emotions

I’ve had dates where I just got off work and needed an extra minute to collect my thoughts. And that’s OK. Break the 4th wall, tell them you want a fun date but need 5 minutes to recover from the day, and you’ll be fine. 

9. Not being Normal

Obviously, don’t be rude.

But that's not what I'm trying to share with you. 

I mean, we already know that:

  • Ordering messy food
  • Eating like a slob
  • Eating too quickly
  • Being rude to the waiter
  • Talking about the food they ordered or how they’re eating
  • Overeating (trying eating beforehand, but not garlicky food - unless you're scared they are a vampire)
  • Getting drunk (don’t arrive from another date or party; also, three drinks max)
  • Nail biting
  • Farting (Pro tip: time it right with a waiter passing by)
  • Burping
  • Cursing (using the F word in every sentence to exaggerate your point)
  • Being aggressive and argumentative
  • Eating with your hands (don’t go for a dinner date in the first place)
  • Picking your ears
  • Eating with your mouth open
  • Spitting

The message I am trying to share with 'Not Being Normal' is that there is no need to pretend to be someone else. Just be yourself and relax. Your date is seeking an honest human connection, not someone who acts like a charismatic superhero.

Trying to imitate characters like Larry David from Curb Your Enthusiasm or Kramer from Seinfeld (see video below) may seem fun on-screen, but it doesn't work in real life.

In other words, it's perfectly fine to be normal.

(I hope we share the same definition of being normal!)

10. Sucking up to your date

Don’t be taking selfies or any other weird stuff.

At the same time, it’s OK if your date is super into you. Let them be into you. Don’t let your brain trick you into only being attracted to the guys/girls you can’t get. 

11. Scared to eat 

I hate dinner dates, but if you’re starving, get some food. 

12. Gifts

Flowers are no longer a thing

Flowers for a romantic date

Dinner dates are way too soul-sucking and formal for that. 

16. Bad date ideas

To learn about where to go on a first date to have fun and avoid dying of awkward silences, read my blueprint, My Top 57 First Date Ideas That Always Work (As a Dating Coach), or click on the thumbnail below:

My Top First Date Ideas That Work Thumbnail datingarmory_com

In short, anything that screams 'TOO MUCH' is a bad idea, such as the example below from Yes Theory

Here are more examples of the worst places to go on a first date:

A) Outdoor Christmas Market

Outdoor Christmas market in the cold rain date idea datingarmory.com

Seems like fun, but in reality, you’ll be too busy walking around to have a meaningful conversation, let alone eye contact.

Plus, it’s probably freezing and maybe raining.

B) Concerts

I bet you're thinking, "Well, I've got an extra ticket, so why not? Plus, it'll be easy to impress them, and I don't like talking on dates."

Well, that’s the problem, you can’t talk at all because it’s way too loud and most concerts cost way too much for a first date. It’s over-investment. [1]

If you love music, go check out an indoor vinyl music sale:

Going to an indoor music sale on a first date

C) Hiking

A couple going on a hike by the water on a first date

It’s cute and romantic, but unless you’ve known each other as friends or coworkers, wandering out into a forest with a stranger is unsafe. 

D) Touristy Stuff

Going to the Odeon of Herodes Atticus, Greece on a first date

Odeon of Herodes Atticus, Greece 

Although visiting touristy places can be fun, they often charge $15 for entry, plus drinks,  and you end up walking around without being able to build chemistry. 

17. Not offering to pay

When going out on a date, offer to pay, even if the guy is expected to pay for the first round. 

If your date insists on paying, don't make it a big deal. 

Pro tip: 

It's also a good idea to carry some cash with you in case the credit card machine is broken, or the establishment only accepts cards for purchases over a certain amount.

18. Ignoring Red Flags

Red flags in online dating are pretty easy to spot:

Looking out for red flags on a first date

So, let’s assume you didn’t catch any craziness in their online dating bio. Well, here are some neon red flags to not ignore on a date:

  1. Inconsistent stories or background.
  2. Signs of Borderline Personality Disorder or other personality disorders. Note: It’s not wrong to date someone with a disorder; just be aware of what you’re getting yourself into. 
  3. Talks too much about their past or future,
  4. Overly critical of people [2]
  5. Too much talk about victimization.
  6. They won’t talk about the basics in their life: Friends, family, or work. Note: Not that you want to talk about work on a first date, but it’s important to cover the basics. 
  7. Being too close-minded to sex. 
  8. Starts talking about being raped or molested. Note: These are serious topics but should not be shared on the first date. 
  9. Shares weird dating and friendship stories from their past. See my post below for more details:
Spotting Red Flags in Your Partner's Past Thumbnail datingarmory.com

19. Bragging

There are too many horror stories where people fake accents, lie about their jobs, talk about how many hot partners they've had, and create fake vacation stories to impress others. 

However, there is a good way to show off, and it's called "Humble Bragging." 

Humble Bragging is the art of showcasing your accomplishments without being too obvious.

In other words, "Tell me that you are fun, sexy, and lovely without telling me."

Share cool stories that show that you're a fun, popular, and lovely person to be around. Just don't make it obvious that you're bragging. 

There's nothing wrong with a little bit of self-promotion.

20. Not Talking Like You’re on a Date

A lot of first date horror stories you hear stem from either personality disorders or, more likely, the fact that we study history for years in school but might read How to Win Friends and Influence People on a boring afternoon. 

We all gotta brush up on our social skills. 

We’ll review some examples, but the general point is this: while on a date, talk about fun things that will build chemistry. 

A) Not being grounded

Although talking about work or boring aspects of life should not be the main topic for a date, it is essential to cover the basics.

  1. Kids 
  2. Past relationships
  3. Work
  4. Life hobbies

And when you talk about them, I don’t care how much you hated your ex or stupid boss; don’t let that negative energy sneak in. It’s a date, not a therapy session. 

B) Not enough sexuality

It’s OK to talk about sexual topics. Yeah, not straight away, but don’t avoid the subject out of being respectful. 

C) 'Not-So-Subtle' Interrogation

We don’t want to waste our time dating another trainwreck, so we casually ask questions to get to know our date better: “How much money did you save up?” or “Do you still talk to your ex-girlfriend?”

We think we’re being subtle, but we’re not. 

They can feel us bearing down on them, and it’s not fun. 

Again, focus on having fun, building chemistry, and making sure that neither of you is a serial killer so you can meet again for a second date.

D) Oversharing

Sometimes, we might have personal issues (personality disorders, family issues, or childhood trauma) that we'd like to share with someone we're dating. 

However, waiting 3-4 dates before sharing personal information is better. 

This is because, on the first date, you want them to feel some chemistry before they make any snap judgments about you. 

Remind me again? What's the point of a first date?

First dates are about having fun, building chemistry, and making sure that neither of you is a serial killer so you can meet again for a second date.

Repeat it with me loud and clear!

First dates are about having fun, building chemistry, and making sure that neither of you is a serial killer so you can meet again for a second date.

E) Talking about Hobbies 

Nuclear Caudillo has a great video on discussing your hobbies on a date, so watch that when you have time, but the TL;DR is this:

  1. Have hobbies. It doesn’t matter if they are sporty, geeky, artistic, or whatever
  2. Talk about your hobbies with passion
  3. Talk about the social aspect of your hobby, e.g., you’re doing car restorations with 2 of your best friends, Rachel and James, and then show pictures. Being the awkward loner at the gym is not sexy. 
  4. If your hobby is especially geeky (e.g., collecting Tintin toys as pictured below), that’s totally fine, and don’t be ashamed, but don’t bring it up unless she brings it up first or the chemistry is there.
  5. Use your hobbies to bring your date home, e.g., "I’d love to show you my paintings/ guitars in my living room."
Talking about hobbies like collecting Tintin toys on a first date

F) Talking too quickly or mumbling

I have struggled with speaking too quickly and mumbling for a long time. This issue became even more ‘pronounced’ when I first started dating. 

So, how did I overcome this embarrassing issue, and how can you do the same?

Here is your daily  Speech Gym Session

  1. Place a pen or pencil between your teeth (see this video).
  2. Practice reading "The Chaos" by G. Nolst Trenite aloud and clearly three times a day for three months.

P.S. Read this for even more tips.

G) Sharing a breakup story

I think it's alright to share why you're single and looking for a partner, but please avoid the details of your breakup.

I mistakenly shared my breakup story once, and there was no second date. I didn't intend to talk about it, but my date asked, and I got emotional without realizing it. Oops!

H) Forcing the talker

If you find yourself on a date with someone who is not talkative, don't worry.

Could you take the lead and keep the conversation going? If there's lots of chemistry, you can even fill in the awkward silences by making out. 

I) Discussing Sad Books

Another way I notice negativity crawling its way into dates is by talking about what kinds of books you're reading. 

Don't get me wrong. Books are great. Even after 1000 years, books are still the best way to learn about anything. 

Still, suppose you're reading "The Book Thief" by Markus Zusak or "Night" by Elie Wiesel. In that case, you don't need to start sharing tragic concentration camp stories from the holocaust. 

J) Mentioning True Love, Marriage, and Kids

First dates are not the time to discuss marriage and kids (even if that's what you're looking for) or that you're in love with them. (Girls have told stories of guys confessing their love on a first date. Like, for FFS!)

And unless you're socially calibrated, avoid making jokes around that subject; people feel there's some truth in every joke. 


  1. "If we got married tonight, I would do...." 
  2. "My daughter is gonna love having you around." 
  3. "We would have cute twins." 

But you can joke about divorce, as pictured below:

Example of playful teasing about divorcing on first dates on Instagram

We called each other Mr./Mrs PP for Proud Perverts lol

K) Don’t talk about dating

While on a date, don’t mention dating, social skills, or anything to do with self-help.


It’s not fun, and it doesn’t make you look cool. 

21. Being Glued to Your Phone 

Everyone knows that looking at your phone on a date is rude, but I'd like to add that while discussing a specific topic, fight the urge to double-check Google to back up your ideas. Try to imagine that your phone isn't there.

22. Uncalibrated Kissing

It’s reasonable to try to kiss during a date, but that has to be done after you’ve climbed the sexual escalation ladder with small touches and building up. If your date isn’t letting you escalate or didn’t escalate, you’ll have to wait for the second date. 

23. Going Overtime

On average, first dates last for two hours, with a maximum of three hours unless they’ll be coming back to yours. 

24. Pushing to go home

If the date is set to be about casual sex, it’s OK to suggest your date comes home on the first date. But don’t be pushy. If they want to meet again, that’s totally fine. 

25. Avoiding sex on the first date

If you like them and you both want to have sex, go for it. Contrary to popular opinion, sex on the first date does not ruin any potential relationship. Don’t say no to sex for the sole reason that this is the first date. 

26. Post-Date Ghosting

If you're not interested in seeing them again, be upfront. But it's okay to ghost or block them if they are rude or you feel unsafe.

27. Sticking too hard to the official date rulebook

Dating is both an art and a science; experience is the best teacher. Please don't rely on a rulebook for every little move. 


If nothing works and you're constantly getting rejected, check with a psychologist for personality disorders, read my recommended books on dating, or better yet, hire me as your dating coach.

As I always say, while I’m not the most charismatic guy, I’ve figured out how to stop being so damn lonely, so I’m confident I can help you too!

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To brighter dating adventures,

Coach Colt 

  • what a cool article, man, I’ve done too many of these things things, but now I can date better because of all my bad experiences and reading guides like this, so thanks!

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    About the author 

    Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

    Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

    My Top 57 First Date Ideas That Always Work (As a Dating Coach)

    Are Coffee Dates Good? It (Kinda) Depends

    17 Basic Coffee Date Tips (From a Dating Coach)

    How to Get a Gay Boyfriend: 25 Tips That Work