10 First-Date Mistakes That Guarantee There Won’t Be a Second Date

We started this discussion by arguing about whether the article should be things men should never say on a first date or things men should never do. We picked both, because turning up late, smelling bad and making a woman carry a giant bouquet around all night are probably worse than one awkward sentence.

Then Mike asked whether we were genuinely explaining first dates or doing it the Terrible Advice way: do these things and make sure there is never a second one. The second version sounded more fun. So talk about your ex, turn dinner into an interview and explain that your mum will always be your number-one woman.

We are talking about a date where you genuinely hope to see each other again. If the whole evening looks completely crazy from the first ten minutes, you normally understand that pretty quickly.

Quick answer: What should you never do on a first date?

• Arrive late and make every decision at the door.
• Turn up unwashed, unshaven or with bad breath.
• Dress for a completely different event.
• Bring a bouquet she has to carry all night.
• Start talking about your ex without being asked.
• Say nothing nice, or inspect every tiny detail of her appearance.
• Ask questions like you are filling out a job application.
• Dump your childhood problems, mum issues and every stupid story about your best friend on her.
• Be rude to the waiter, or be too scared to ask for the food you ordered.
• Spend the whole date performing, rush physical contact and forget to ask whether you even like her.

The main point of a first date is to see whether you have chemistry. Have some control over the basic details, then stop making the whole thing more complicated than it needs to be.

1. Arrive late and decide everything at the door

Being late happens. As soon as you know, tell her and give her an honest arrival time. Do not send “five minutes away” while you are still standing in the shower.

Turning up with no plan is a separate mistake. You do not need to control every minute of the evening, but decide where you are going before you meet instead of arriving late and asking, “So, where do you want to go?”

A date is basically a little football match anyway, and it is easier when the match happens at your stadium. That just means somewhere you already know, somewhere you like and somewhere you can handle without checking Google Maps every four minutes. If she suggests a place herself, that is completely fine. The evening does not become any less yours because she picked the restaurant.

It is still worth researching the place. Check the restaurant’s Instagram to see how people dress there, book a table and ask whether you can sit somewhere that is not next to the toilet. Find out whether it becomes insanely noisy at that time or whether somebody has booked half of it for a birthday party.

Better to know this before you are both sitting there like two idiots, shouting over a banquet you did not know existed. Details matter. If you sort out the easy ones, you have already won half the battle.

2. Don’t wash yourself

Showing up prepared does not mean reading a course on first-date psychology. It means washing yourself.

Have a shower, shave if you normally shave, brush your teeth, use deodorant and put on clean clothes. Nobody has ever lost points for arriving clean and smelling good.

If shaving usually leaves your neck red, do not attack it against the grain just because the date is tonight. Our guide to getting a close shave without the irritation will help more than dragging the razor over the same patch twelve times.

Bad breath matters too. Gum helps, but if you are unsure, breathe into your dad’s face and ask for a verdict. Your mum loves you and may decide not to destroy your confidence. Your dad will probably go, “Bro, you stink,” even when you do not. Somewhere in there is useful information.

3. Dress for a different event

Even if you are naturally a three out of ten, sorting out your clothes and looking clean can add two points immediately. For men, two points for one clean shirt is a very good deal.

A decent shirt or a clean white T-shirt can be enough. The clothes should fit, smell clean and make sense for the plan. Dinner may call for something a little smarter, while an amusement park or anything active needs clothes you can comfortably move in.

She already agreed to the date, so there is no need to arrive dressed as a completely different man. Make an effort and stay recognisably yourself. If you want to improve more than the shirt, our five simple habits for looking and feeling better start with the things that matter before you buy another grooming product.

4. Bring a giant bouquet

Flowers can be a lovely move when they show that you put some thought into the date. A random bouquet grabbed on the way shows less thought, while a huge one gives her a new job for the evening: where is she going to carry it?

Not a thousand roses, not a hundred roses. Even a normal bouquet becomes awkward when there is nowhere to leave it and the two of you might move somewhere else after dinner.

Before buying anything, do two minutes of detective work. If you know one of her friends and can ask without making the whole thing weird, find out which flowers she likes. Otherwise, her Instagram probably has a birthday photo somewhere with enough evidence. Be Sherlock for two minutes, not a private investigator. You are looking for tulips, not reconstructing her movements since 2019.

Then get something small and neat. One flower works, as does a compact arrangement similar to one of those little wedding bouquets. It is easier to carry and feels far more personal when you picked something she genuinely likes.

Flowers are not compulsory. If you bring them, just think logically about what the rest of the evening looks like.

5. Definitely tell her about your ex

Girls love hearing about the ex. Tell her the name, where you went on holiday, why the relationship ended and exactly which parts of her personality drove you insane. If possible, make it clear that you are completely over her by talking about her for forty minutes.

If your date asks, “What happened in your last relationship?” then obviously you can answer. You have a past. Just answer the question without letting your ex take over the evening.

The point is not to start telling her about your ex unless she asks. You do not want to give her a reason to think you still have not got over the relationship. Keep the answer honest and normal. Do not spend the whole time insulting your ex either, because now the woman across the table is probably wondering what you will say about her one day.

And do not try to improve your value by announcing that other women are always interested in you. If it comes up naturally, fine. If you deliberately perform the whole “yeah, I’m such a womanizer, girls are always after me” routine, it will sound exactly like what it is: an attempt to impress her.

6. Say nothing nice, or overdo every compliment

Compliments matter, but so does balance. When you meet her, tell her she looks good. She probably put some effort into getting ready, and it is nice to show that you noticed.

A specific detail can feel more sincere than repeating “you’re beautiful” all evening. Maybe her fringe looks good, the manicure suits her or she has a great laugh. Mention whatever genuinely caught your attention.

There is no need to inspect every tiny detail or spend five minutes analysing why one shade of nail polish works with her skin. Say something real and continue with the conversation. Timing and sincerity matter more than the number of compliments.

7. Make the conversation as boring as possible

Basic questions are normal. What do you do? Where are you from? Fine. The problem starts when the whole evening becomes question, answer, question, answer. “What ethnicity are you?” and “Where do you see yourself in five years?” are a quick way to turn the first date into a job interview.

Most of the conversation should be light and easy. Ask about her actual life instead of firing standard questions and waiting for your turn to speak. If she tells you about going to Italy with her friends and mentions falling over somewhere, pick up on it later. It shows that you listened, even if it was not the greatest story you have ever heard.

You can ask something slightly deeper when it fits. What is her favourite childhood memory? What would she do if she had all the money, time and opportunities in the world? What has she become strangely obsessed with lately? Those answers tell you more about somebody than another discussion about job titles.

Do not prepare fifteen “deep questions” in your Notes app and work through them in order. Listen and follow what she says. You do not need to perform comedy either. If jokes are not your strength, forcing one every two minutes will only make the date stranger, and she may be funnier than you anyway. Paying attention will take you much further than another joke that does not land.

8. Tell her every problem you have ever had

You can be honest about your life without handing somebody the complete case history before the starters arrive. A woman who has known you for forty minutes probably does not need every childhood problem, family fight and emotional wound in one sitting.

It is good to care about family. It normally says something positive about you. Just do not spend the evening explaining how much you love your mum, how she is your number-one woman and how you would choose her over your future wife. Your mum can remain important without joining the date.

Filter the stories slightly too. The night you and your best friend threw up while riding a sled was probably hilarious. We believe you. Maybe save it until she knows you a little better.

Being yourself does not mean telling her every stupid story about what you and the boys do when nobody sensible is around. Keep some material for the second or third date.

9. Either bully the waiter or become scared of him

If the date happens at a restaurant, she is going to notice how you treat the waiter and everybody else around you.

Do not bark, “Where is my menu?” or speak to staff as though they are beneath you. Nobody is going to confuse that with confidence. You just look pleasant to the woman you want to impress and horrible to somebody who has to serve you.

At the other extreme, do not be too scared to call the waiter over. If you raise your hand and nobody notices, politely get someone’s attention. Get up and say, “Boss, we’re sitting over there. Could you come over when you have a second?” There is no need to be rude. That is enough.

If they bring the wrong food, say so: “Sorry, I don’t think this is what we ordered. Could you check it for us?” You are not starting a war. You are asking for the dish you ordered.

One of us used to be too scared to do this as a teenager and would eat whatever arrived. He still tells the story as though several restaurants tried to assassinate him. In reality, he survived every meal and eventually learned to speak to waiters.

That is the balance: do not dominate the room, but do not disappear inside it either. A calm sentence usually fixes the whole problem.

10. Forget that you are deciding too

The whole point of a first date is to work out whether you have chemistry. While making a good impression, pay attention to how the evening feels from your side too.

Notice whether you enjoy talking to her, feel comfortable around her and genuinely want another date. It is easy to become so busy trying to win approval that you forget to check your own reaction.

What about small touches on a first date?

Small touches can help when the chemistry is already there. We mean a brief touch on her hand or shoulder, nothing extreme. The lower back is more intimate, and grabbing her ass because she laughed at one joke is not a “small touch.” We would rather not discover our first legal case through the Terrible Advice section.

Then pay attention to how she reacts. If she stays close, touches you back or seems comfortable, fine. If she pulls her hand away, moves back or looks uncomfortable, stop. If you are genuinely unsure, ask. Most men have misread a moment at least once, especially when they were younger and nervous. It is awkward, but it does not have to become a disaster.

Just say, “Sorry, I get a bit nervous around beautiful girls.” Girls will usually find that kind of honesty cute. Either way, give her a little space and let the conversation move on. Misreading one moment is natural; repeating it after she has shown you no is where the problem starts.

If halfway through the evening you realise she probably is not your person, do not suddenly switch off and make the rest of the date awkward. Stay engaged, finish it properly and be honest afterwards: “I had a good time with you, but I didn’t feel that spark. I don’t think we’re the right people for each other, and I don’t want to waste your time or mine.”

If it went well, ask how she is getting home. Put her in a taxi and pay for it when that makes sense. Ask her to message when she arrives. Open the door. Pull out the chair if it feels natural. Gallantry has become less common, but basic manners still work.

Do not overcomplicate the whole thing. Try to have a good time and see whether you both want to do it again.

So, how do you get a second date?

None of this requires a course in female psychology. Turn up on time, wash yourself, wear something appropriate and put a little thought into where you are going. Listen when she talks, treat the waiter like a human being and do not make her carry a hundred roses while you explain why your ex was crazy.

The hardest part is stopping the performance. You do not need every woman to think you are perfect. You only need to work out whether the two of you genuinely enjoy being around each other. If you do, make it clear that you would like to meet again. If you do not, be polite and do not waste her time.

One of you will probably say something awkward. That is normal when two people who barely know each other are both nervous. Worrying too much about looking cringe only makes you perform harder. Make an effort, pay attention and see whether you both want to do it again.

Good luck.