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What Am I Doing Wrong on the First Date?

By Emyli LovzMay 25, 2018First Date
what am i doing wrong on the first date

Hi guys, Emyli here — your dating coach for men. Different versions of the question, “What am I doing wrong on the first date?” is something I often encounter when working with my male clients.

So your first date went bad — now what?

More often than not, a successful first date doesn’t happen by accident or when you simply “wing it.” Luckily, there are several strategies you can use to ensure the first date will be a success. You can even lock down a second date when using these strategies!

Check it out.

Tip #1: Stop Forcing the Conversation

Think back to the conversation. Did talking to her feel forced? Instead of asking yourself “What am I doing wrong on the first date?” briefly change that question to, “How did the conversation go on the first date?” Take a look at the list below, and ponder whether or not one or several of these scenarios seem familiar:

  • You found yourself accidentally asking the same question twice because you couldn’t think of anything else to talk about.
  • You talked about the weather A LOT — and you don’t even really CARE that it’s supposed to rain next week.
  • You read all the specials on the menu aloud because you couldn’t think of anything else to talk about.
  • She was pretty much dead silent.
  • You could drive a bulldozer through the awkward silences in your conversation.

Sometimes first date conversations become forced because there is simply a lack of chemistry between the two parties — and that’s OK. But a lot of times, conversations go kaput because one or both people allow nerves to get in the way and — more importantly — haven’t done any pre-date prep in regard to the conversation.

When you’re on a first date with someone, particularly if it’s someone you don’t know very well or met online, making conversation can feel a bit unnatural. That’s why it’s important to have some first date questions prepared BEFORE you two have even met at your agreed upon location.

Check out my article on the Top 25 Questions to Ask a Girl on a First Date for a TON of inspiration on how to break the ice. Here are a few of my favorites to get you started:

  • “What is your best childhood memory?”
  • “Are you a morning person or a night owl?”
  • “What would constitute a ‘perfect’ date for you?”
  • “How would your friends describe you?”
  • “Do you think goldfish make good pets?”

And if she gives you one-word answers, offer a follow-up question to try and keep the conversation going. Once these questions stimulate a more interesting type of conversation, things will flow in a more natural way.

Tip #2: Stop Treating the Date Like Work

Before I embarked on my 100-date experiment, I never realized just how much FUN dating could be. A lot of people see “getting out there” in the dating world as a necessary evil on the way toward finding a long-term, committed relationship.

And when you go into a date feeling nervous, self-conscious, and worried about things going terribly awry, it’s no wonder you would end up asking yourself a question like, “What am I doing wrong on the first date?”

You need to change your mindset so that you’re not entering a date expecting the worst — that causes a self-fulfilling prophecy when it comes to dating.

So how do you make dating more enjoyable and less stressful?

Don’t Be Outcome-Focused

When you’re constantly fixated on the end goal (i.e., getting a serious girlfriend), that fixation can end up sabotaging your date.

It’s really important to enjoy the process of dating and try to stay in the present moment as much as possible.

I talk more about this and other ways to reduce anxiety while on a date in my article, How to Be Confident When Dating a Girl You Like.

Tip #3: Ease Her Nerves

Sometimes, if the person you’re on a date with seems nervous, your knee-jerk reaction is to assume that WE’RE the ones doing something wrong.

And — suddenly — you’re feeling nervous too.

Remember that a girl feeling uneasy during a first date likely has NOTHING to do with you. There can be a variety of reasons that she feels nervous on a first date, such as:

  • This is the first time she’s been on a date in a while.
  • She recently had a bad date experience and is worrying the same thing is going to happen this time.
  • She had a stressful day and is flustered because of it.
  • It’s the first date for her too, and she’s having the exact type of anxieties you’re having.

So how do you handle this?

The less stressed and more confident you are during the date, the better she will feel. And once you’re both loosened up and comfortable, things will just start to flow naturally.

Here are a few things you can do to ease the tension:

Warm Up Before the Date

When advising my clients, I always recommend that they “warm up” before a date by having something planned about an hour and a half before you’re supposed to meet her.

Socialize with friends or the baristas at you local coffee shop to get you in the mood for conversing. At minimum you could simply go outside to a park and catch up with a few friends on the phone. 

This type of happy distraction can make all the difference when it comes to making a great impression on her during your first date.

Make Sure That You Use a TDL

Rather than always ask yourself, “Is this first date going to be another brutal failure?” consider how can make it better before the date.

A perfect first date always involves using a TDL. 

A TDL is an acronym used to describe the three critical components of a date’s request call-to-action:

  • “T” is for Time: The exact time the date things will take place.
  • “D” is for Date: The date you will meet. It’s important that you ask for a specific date and time so that she can let you know she is available and neither of you will be in limbo between talking and actually meeting up in person.
  • “L” is for Location: Make sure that the location is somewhere close to where she lives and safe.

It is imperative that you use a TDL each and every time you ask a woman out during the early stages of dating. Using a TDL is chivalrous, shows initiative and — when you have a concrete plan — it’s one less thing for you to worry about before and during a first date.

Closing for a TDL also forces you to come up with date ideas, which SHOULD make you reflect on her interests and how to incorporate them into whatever plan you come up with.

Before every one of your first dates, I recommend that you brainstorm and create a compelling date #2 for whomever you’re taking out. Propose your TDL to her while you’re still together on date #1. Then watch your success skyrocket. 

Learn more about what TDL and how to use it here


Another thing you can do if you feel like the girl you’re on a date with is une being sure to smile — don’t reciprocate her worried look with your own worried look.

Studies show that smiling — even when it’s a fake smile — can boost mood and decrease stress. And when you’re less stressed, she will be too.

Tip #4: Make the Date More Playful

When putting yourself out there in the dating world, it’s SUPER EASY to fall into a routine of going out to a bar for a happy hour or grabbing a coffee.

Try spicing things up by getting more creative with your plan. Based on her interests, consider the following date ideas:

Nostalgic Dates

Get more playful by choosing a nostalgic date, such as:

  • Bowling
  • Mini-golf
  • Frisbee, followed by a picnic lunch
  • Riding the Ferris wheel at a local fair or carnival

Active Dates

Getting active on a date is a great way to get the endorphins flowing so that you’ll feel less stressed. Plus, having an activity you both are enjoying will naturally break the ice and fill in awkward pauses. Consider these ideas:

  • Cycle to a chic cafe or eclectic bar.
  • Take a walk on the beach followed by a quick bite to eat or drink.
  • Go hiking.
  • Build some endurance and an indoor rock climbing gym.

Fun Indoor Dates

And lastly:

  • Throw away your inhibitions at a karaoke bar.
  • Visit a museum.
  • Go on a brewery tour or do a wine tasting.

You can learn a lot more about ways to be more playful on dates by reading my recent article, How to Make Dating Fun and Enjoyable.

Tip #5: Arrive Early

It’s really important that YOU are at the location of the date early, so that she sees you when she gets there.

There’s no such thing as being “fashionably late” when it comes to a first date. Being late is not fashionable — it’s frustrating. No girl likes to be sitting at a table or bar by herself, receiving a “Running late! Be there in 15!” text or — even worse — no text at all.

You want to make sure that your first impression is a GREAT one. And when you’re late, you’ve automatically gotten things off to a rough start that may not be possible to recover from.

Guys, this is just like being late to an interview – it’s not good. 

Tip #6: Make Sure That You Are in Plain Sight

Now that you know to arrive early, let’s take that courtesy one step further.

Once you arrive at the date location, text her to tell her where you are and what you’re wearing so that she doesn’t have to guess or run around the place looking for you.

This is particularly important when you are meeting a girl you met online IRL for the first time.

Also, ask yourself,  “Am I standing somewhere where she can easily find me when she arrives?

Try to be in a location that is close to the entrance or easily visibly. Don’t stand somewhere super far in the back or where you’re surrounded by a gaggle of people.

And speaking of a gaggle of people…

Tip #7: Don’t Take Her to a Place That’s Super Crowded

Choosing the a super busy environment is a sure fire way of messing up a first date. 

Do you take her places that are super crowded? If it’s a bustling location, the noise and claustrophobic atmosphere could prevent you from building any real kind of chemistry.

Make sure you research the places you want to take her and choose locations that are more intimate and tend to not draw a huge crowd.

Tip #8: Check the Weather

Make sure that you keep the weekly weather forecast in mind before selecting a first date location.

An outdoor date is perfect for a beautiful, sunny day. But if it’s raining or extememly windy, find a nice, intimate indoor date — preferably somewhere that has a cool fireplace you can sit by.

If she seems particularly excited about getting some fresh air on your date, match the date to a sunny day — and let her know. For example:

“It looks like the next couple days are going to be pretty gloomy. Sunday is supposed to be gorgeous, though. Are you free to go hiking at LandsEnd on Sunday at 11am?”

This shows that you’re taking her interests into consideration when planning the date, which is chivalrous and appealing.

Tip #9: Have Her Coffee Ready for Her

Good first dates always involve meticulous preparation. If you decide to do a date at a cafe, ask her how she takes her coffee before the date (you can do this during a text that also confirms that the date is still on). THIS way, you can have it ready for her when she arrives.

Not only will this make a great first impression, but it eliminates the awkwardness of having to stand in line or manage the payment process in front of her.

Tip #10: Tap Into Your Inner Storyteller

You’ve got great stories and great experiences outside of your dating life. So if you’re still wondering, “What am I doing wrong on the first date?” consider bringing the most interesting things in your life on the date with you.

Let’s take the example above, where you’re taking her to a cafe to grab a coffee. Don’t let the coffee be the whole date. Use that location to tell her a compelling story about an experience you had at a place (which will be ever-so-conveniently within walking distance of the cafe you’re at). Then move the conversation* to the place you started telling her about. 

*Note: Pay attention to what she’s wearing. You don’t want her spilling coffee on a nice white dress or shirt because you’re walking about and talking with the coffee.  Make sure to stop and sit to drink the coffee or just pause to give her time to drink it first, then walk around. You can easily stand to watch the people around you. If you’re in San Francisco at The Warming Hut, you can stand and watch the fisherman, stand and watch the kite boarders, just really focus on being present in the moment and allowing the location you chose to do the majority of the work for your conversations. Give her a second to sip her coffee because it is going to hit her and she’s going to feel more energized and connected to you once she gets a little caffeine in her bloodstream.

Make the walk to the new location compelling by telling her a story about why it’s so epic.

You always want to tell great stories and entertain her. By doing this, you will keep her mind active, and that won’t give her time to think about feeling awkward or insecure.

And just as you don’t want her to be ruminating during the date, make sure you don’t get stuck in your head either.

Avoid over-intellectualizing your stories. Focus on feel-good stories that spark a positive emotional reaction — not an intellectual one. Use less words, focus more on the beautiful environment, and talk about things related to the present moment.

Tip #11: Ask Questions Related to Family

Ask deep questions that can build intimacy during the first date. Some of these questions could include:

  • “What is your favorite childhood memory?”
  • “Which members of your family are you closest to?”
  • “What were you like as a kid?”
  • “Does your family live here or are they out of state?”

One thing to REALLY keep in mind here is relevancy. Use these questions when it seems relevant to the conversation or environment.

Sometimes family-related questions might not be relevant if you’re in an environment that’s really rich and has a lot going on. Conversely, you may be in a calming, intimate environment that makes deeper questions come naturally.

Tip #12: Take an Improv Class

Focus on interactive activities that might interest you outside of your dating life. This will help you eliminate your “I messed up the first date again” mentality. 

Improv classes are great places to learn how to really be present and not in your head. Improv forces you out of your head because you have to be responding to the environment around you.

Below are a few examples of improv games that can help you be more present and able to think on your feet:

Fortunately, Unfortunately

In this game, you will create a problem, then solve it.

One player will make a statement and then the other person finds something unfortunate about it. First, player A will make a statement. Then, player B will find something unfortunate about that statement. Player A will find something fortunate about THAT statement and so on and so forth.

For example:

“Fortunately, it’s Sunday today.”

“Unfortunately, tomorrow is Monday.”

“Fortunately, it’s my coworker’s birthday on Monday, so I’ll get free cake.”

“Unfortunately, your coworker just gave up sugar”


In this game, the first participant of an improv scene much start with the first letter (or a chosen letter) of the alphabet. The next participant who speaks needs to say the next letter of the alphabet, and so on. It’s a challenging game, but a fun one!

“What Am I Doing Wrong on the First Date?” Wrap-up

I hope this article has helped you uncover some solutions to what you may be doing wrong on a first date. If not, it’s OK. You are not alone. 

They don’t teach Dating 101 lessons in school and we certainly don’t learn the nuances of the dating world on the playground. It takes practice and strategy to really let go of your inhibitions and ENJOY a busy dating life.

One of the main strategies I used during my 100-date experiment is megadating. Megadating is a dating process that involves dating several different people at the same time.

This process makes dating FUN, because it naturally increases confidence, reduces stress, and prevents you from settling — because it shows you that there truly ARE plenty of fish in the sea.

If you want to learn more about megadating, as well as other strategies to help you CRUSH your dating goals, head over to my calendar and book a 1-on-1 Skype session with me today. During our session, we’ll discuss your dating roadblocks and come up with an action plan to help you find your next relationship!

I also invite you to check out my Dating Profile Services and comprehensive online dating course.