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10 First Date Mistakes You Are Probably Making

Updated on April 28, 2015

They said they would call...

Have you ever been on a date and wondered why they never called again? Did you think the date went really well and then two weeks of dead air later you are making excuses like, "he's just really busy with work" or "she did mention her grandmother was sick". Here is a list of top ten first date errors I think we have all committed at one time and that is why we never got that follow up phone call for a second date. Live and learn, ladies and gentlemen. Live and learn.

10. You are not dressed for the occasion.

One common mistake people make when dating is they are not dressed properly for the occasion. As a professional matchmaker, it is a complaint I have been hearing for years, and as often as I have corrected said issue, it always seems to rear it's ugly head again and again. The excuses and reasons people give are even worse than the attire itself. Too often my clients will say, "well, we were going to a casual place. So, I thought shorts were okay." No. They are not okay. Shorts are acceptable if you are going to the park for a picnic, but not to a casual lunch or cocktails. This goes for both sexes, not just men.

Ladies, being dressed appropriately is extremely important for a first date. If you are wearing skin tight clothing, you are sending a different signal than if you wore a nice dress. Take it easy on the perfume, make-up, and jewelry. Cleavage is acceptable, but limit it to less than 1.5 inches vertically. More than that, and you are sending an "I'm easy" signal.

The opposite is just as important. No one wants to date a woman who is frumpy and looks as though she doesn't care. If you don't wear make-up, put on a little gloss and mascara. No one is asking you to contour your face and put on a whole mask, but do make some sort of effort. I love natural beauty, but it doesn't hurt to add a little something special for a first date.

The best advice I can offer as far as what to wear is to wear your favorite "oh wow, I look damn good in this outfit" outfit. First dates are somewhat hard to come by, but second dates are even harder.

This outfit belongs in a nightclub. Not potentially meeting someone you could spend your life with.

9. Location, location, location.

First dates already make people nervous, but when you can barely hear your date due to the high volume of people in the restaurant, it sets the tone for disaster. Location is crucial in creating a successful first date situation. You want to be able to hear your date clearly and have few distractions. While busy restaurants are not ideal, sometimes they cannot be avoided. Meeting your date anywhere on a Friday or Saturday night is going to be crowded, but you can find ways around that. Ask to be seated in a quiet area and a booth, if that is an option. Avoid crowded bars or live bands at all cost. Otherwise, your date is mostly just nodding their head in agreement and smiling due to the fact they have no idea what you are saying but don't have an immediate solution to it.

Coffee shops are not romantic at all, but people still flock to Starbucks for first dates. So, if Starbucks is your "go to" first date spot, be sure to find a nice corner to get acquainted in.

If you are on a limited budget or you are a serial dater and don't want to spend a $100 on every first date, get creative and find something else to do together. Here are some things you can do on a limited budget: get a snow cone (who doesn't love snow cones?), frozen yogurt, botanical gardens, museums, pack a picnic, wine or distillery tour, and the zoo. Never take a first date window shopping, walk in the park, or movies.

Cocktails are always safe and cost efficient. If they have more than two glasses of wine or more than two mixed drinks, be concerned there may be a bigger problem there. Which brings me to my next point.

Two Drink Maximum Rule

8. Drinking Too Much

We all like to have fun, let our hair down, and have a few cocktails with friends. However, a first date is not the time or place to let such hair down. I like to believe there is an unspoken rule of a two drink maximum for a first date. I am not encouraging you to be something you are not, but I certainly don't believe getting a little buzzed on a first date is a good idea either. Inhibitions quickly become altered when alcohol is involved and conversations can become too loose for a first date. You want to stay lucid and self-aware throughout your first date so you can easily determine if this person is worth a second date.

Of course, there are exceptions to this rule, such as a date that lasts longer than 3 hours, or a date that has wine tastings, etc.

7. Talking Too Much

Talking too much on a first date will cost you a second date. I realize when people are nervous, they ramble. However, there is a cure to that ailment: ask questions. When you notice yourself talking too much, stop, take a deep breath, and then ask them a question. Typically when people are talking too much, it results in them over-sharing. First dates are about getting to know each other, but not every detail of your life. Keep the conversation even by asking follow-up questions and answering your own questions after they finish speaking.

Some details to leave out of your first, second, and third date conversations are: health problems, financial difficulties or how much money you do have, anything to do with your ex, major problems with children, how much you hate your job, and very negative subjects. While some of these are hard to avoid, try to limit such conversations to 30 seconds or less.

6. Blowing Off the Date Because You Aren't Attracted to Them

Single people everywhere are finding themselves in awkward situations when they show up for a first date only to find out their date looks nothing like the photo they viewed online or they find the same person in the photo but don't feel any chemistry. These kinds of dates can go from bad to good by adjusting your take on this whole situation, because you are already there, might as well make the best of it. Plus, being rude or sneaking out the bathroom window is only something someone with low morals would do.

A good practice is to continue the date as planned, minus the fact there isn't any chemistry. You agreed to go on this date initially, because you thought you had enough in common to make a go of it. Thus, leaving you with a new friend at least. You can never have too many friends, and the best part is, you never know who they are friends with. Your date may like to play matchmaker and set you up with one of their friends in the future. Dating is all about networking!

5. Dinner Etiquette

This is broken into two sections for men and women, because each group breaks many rules of dinner etiquette for dating.


Women have formed a name for themselves as the "I eat like a tiny bird while on a date" gender. Good one ladies. Men think we can just live off of fumes and two croutons thanks to that outdated movement. While on a date, instead of eating like you never eat, eat normally. Order what you would order when you are out with a girlfriend. Now, I am not saying ask for your own personal queso because you have decided to really get it on tonight, but order the same things you always order. He has already decided if he is interested or not when he first laid eyes on you. Might as well show him the real version up-front. Pretending to be something you are not is only going to lead to misrepresentation, ultimately leading to your break-up in two years because he found out who you really are and you actually eat food. I know women have heard this before! Please stop pretending to only eat salads all the time when you know you order the Old-timer with cheese and bacon at Chili's!


The number one complaint about men I hear from women when it comes to dining etiquette is terrible table manners. Now, I am not talking about how to use which fork. I am referring to inviting a lady to dinner, getting seated, then taking 30 minutes to order a damn appetizer because the "conversation has just been so good". No conversation trumps hunger. She is just too polite to interrupt you and mention she is wasting away on her side of the booth and her blood sugar is dropping. Be considerate enough to ask what kind of starter she would like and get that puppy going within the first ten minutes of sitting down. Hunger and thirst lead to her thinking about that, instead of thinking about how cute you are.

Go ahead and eat the burger if it's what your little heart desires!

4. Asking Inappropriate Questions

What is inappropriate, you might ask?

  • How much money do you make?
  • What kind of car do you drive?
  • How much is your house worth?
  • Why did you get divorced? (This question is better to be saved for date number 3 or 4, not the first date!)
  • Why don't you have full custody of your children?
  • I did a background check on you. What is this misdemeanor from 2007?
  • What is that bump on your face?
  • Since you are in the medical field, what should I do about (insert medical illness here)?
  • Can I stay with you tonight since it is a far drive home for me, and we have been drinking?

All of these, every single one, is out of line for a first date. One day, down the line when you are both in a committed relationship, and you have broken the boundaries of intimacy, you can ask all of these questions. But, if you have any hopes of getting a second date with this person, avoid those and related questions.

3. Your body language is sending the wrong signal.

Body language is what your words aren't saying. The placement of your hands and facial expressions are going to speak to your date, and with that information, they are determining if you feel chemistry and if they feel it as well. The best practice is to remain calm and collected. Do not fidget with napkins, the silverware, stirring your drink excessively, touching your nose, eating the crumbs off of your plate or crushing the ice in your empty glass with your teeth. Relax. Try to enjoy yourself. Try to remain positive as you start to make a new friend.

Is the sun in her eyes or is she confused? See how hard it is to interpret body language...

2. You end the date terribly.

It is all about the close! Like I said before, when a date doesn't go as planned, improvise! Make the best of something failed, and make sure you end the date on a good note, while still being honest.Try to end it with a nice hug and a "I'll call you sometime, and we'll hang out again". Light and breezy. No commitments, but not a complete blow off. Then, the game plan is to get in touch with her/him in the future to just get a beer, and over said beer, mention you think she/he is a great person and someone you would value as a friend. They will hopefully take your gesture to get a drink as an olive branch and accept. Later, you'll meet their friends and they will meet your friends. Everyone is happy!

Men: always walk a girl to their car. This is another one of those "if I had a dollar for every time I heard a woman complain that a man didn't walk her to her car and that is why she won't go out with him again" stories...

On the other hand, when the date went well and you are hoping it will end even better, and then you bomb it. Don't go in for a kiss on the first date. Be more suave than that and go for a hug and a kiss on the cheek and maybe throw in a kiss on her hands as well. Romance is a lost art and if more men watched black and white movies, women would be swooning over them. Intimacy is better when served nice and hot. I like to call it marination. Don't sleep together or make-out on the first date. You'll have less to look forward to. This could possibly be the same face you have to make-out with the rest of your life. Savor it.

Marination definition: dating someone a few months before ever having sex, building up all those anxious desires to truly be with one another. Oh lord, just gets me thinking about those first few months in the beginning of my relationship with my boyfriend. Whew!

Respect your date! Put your phone away.

1. Your cell phone is the third wheel on the date.

Cell phones have become a staple in dating and communication with just about everyone. However, I cannot imagine an extremely pressing matter so important that your cell phone needs to be placed on the dinner table/bar top. Those who are that important (brain surgeons on call, firefighter on a lunch break, or someone equally important in those types of expertise) that actually need their phone within eyesight typically aren't putting it on the dinner table on a first date. Instead, they have it on vibrate, like other smart people, and place it in their pocket. If their cell phone is on the table, consider them to be self-evolved so much they believe themselves to be too important to ever miss a phone call.

Do not check your phone while on your date...unless your date is in the bathroom. Then, and only then, is it okay to check your phone or text your friend that you are still in one piece and not stuffed in the trunk of your car.

Do not show your date more than one photo on your phone. For example, "here is a picture of my dog, since you mentioned how much you love dogs," or "yep, this is the house I have been working on with habitat for humanity". These are things people want to see on a first date. Not just more pictures of you standing in front of things and you saying, "this is me when I went to Italy standing in front of this statue". Blah. Check please!


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    • dashingscorpio profile image


      3 years ago

      Lori Gottlieb wrote a book that became a bestseller titled:

      Marry Him: The Case for Settling for Mr. Good Enough

      Although I've never read the book I imagine it's geared towards unhappy women who have chased after the "bad boy" or the guy that every other woman is clamoring after; 6'2", good looking, high paying career, charming smooth talker, naughty sense of humor, and a masterful lover.

      Some of these women have had their hearts broken time and time again or the men they invested time with have no intention of marrying them.

      Mr. Good Enough is the UPS driver, shoe salesman, butcher, mechanic, truck driver, insurance salesman, mailman, butcher, pharmacist, or whatever who lacks the "flair" of a dashing prince but he has a steady job, is honest, reliable, adores his significant other and most of all is safe to trust.

      During her early youth this woman would have never looked twice at such a man. However after years of heartbreak and watching the clock tick she's open to expanding her "mate selection requirements" to possibly include someone who is shorter, overweight, and bald but has a heart of gold.

      You're going to have a real challenge finding a decent looking man to adopt that philosophy when it comes to choosing women to date.

      We still live in a society where men are taught if they become really successful they "can have any woman" they want. Many women still believe if they're "hot enough" there are men who will pay their bills for life but they have to cash in while they're still young enough to attract them. In the U.S. the richer and older the man is the younger his wife is.

      At age 86 Hugh Hefner founder of Playboy Magazine married a 26 year old woman. It's doubtful we'll ever see this the other way around no matter how rich the 86 year old woman may be.

      Hefner in theory should be chasing after Betty White! :)

    • The Matchmaker profile imageAUTHOR

      The Matchmaker 

      3 years ago

      Thank you dashingscorpio!

      Women (such as myself from my days of singleness) will go out with men that are not the best looking, because we want to increase our odds of finding a compatible partner, not just a pretty face. It's like when you see a really attractive woman with a less than average looking man. We usually like to think in our heads, "oh she's in it for the money" or "maybe he used to be good looking". Reality is she has found someone who makes her laugh, listens to her when she wants to talk, and overall makes her feel special. At age 80, we all look the same: OLD!

      As a matchmaker, training men to stop going for looks first is a challenge, but I have noticed they aren't attracted to good looking women with no confidence. That is also a deal breaker to most of them.

    • dashingscorpio profile image


      3 years ago

      Voted up and awesome!

      "First dates are about getting to know each other, but not every detail of your life." and "Your cell phone is the third wheel on the date" are priceless!

      Too many people have forgotten that dating is supposed to be FUN!

      This is especially true of a {first date}. If both people don't (relax) and have an (enjoyable time) odds are there will not be a "second date".

      The goal is to find commonalities, establish rapport, and see if you have chemistry. Having said that I believe both men and women are guilty of #6.

      "Blowing Off the Date Because You Aren't Attracted to Them!"

      This is especially true of men. We're not known to ask women out on dates whom we find unattractive in the first place. No guy says I'm going to spend my hard earned money on woman whom I consider to be ugly but has a nice personality. We tend ask out women we have romantic interest in.

      However I've heard of women especially those beyond age 30 who will go out on dates with men they find unattractive. However many of them do so just for the activity of the date or to have something to do. They're put off by these men when they attempt to kiss them good-night.

      Therein lies a major difference between how men and women approach dating. A man only asks women out whom he finds physically attractive and has a romantic interest in. Whereas a woman may say yes to date and have no romantic interest in the man. It's no wonder why dating is such a challenge. Both genders (assume) they're reading from the same playbook!

    • profile image


      3 years ago

      Wonderful advice as always!


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