5 Ways to Impress a Woman on the First Date

First dates can be some of the most magical experiences, or they can be downright panic inducing!  

A good first date can make time fly by and make you feel like you’re walking on clouds.  And a bad first date can feel like the longest, most uncomfortable hour you’ve ever spent.  But, for the most part, both of these dates start at the same place: “Hi, nice to meet you!”  

It’s what comes after that can make or break the date.  So many guys are worried about the perfect opening line, or the perfect place to go, when it’s always more about the connection and what you do and talk about that will send you to the winner’s circle.  So let’s brush up on a few first date basics!

I know that there is a lot of advice out there for guys on dates saying, “Ask a lot of questions! Women love to talk about themselves.” Look, we all like to talk about ourselves, but it’s not about the quantity of the questions. It’s about their quality.

I’ve had some of my female clients say that the men will just pepper them with one question after another, without any follow up or reciprocity.  But, especially on first dates, you need to ask the right questions as you’re getting to know each other. 

Instead of doing the “dating interview,” try to have a genuine conversation. Don’t just sit across from a woman and go down the list of questions you’re “supposed” to ask. What do you do? Where are you from? Where did you go to school? These are all logical questions, but often the less-experienced dater will make the process more of a quiz than a conversation.

Every dating question can be asked to provoke an emotional response. Some examples would be: What’s one of your fondest childhood memories? What’s the best local food where you’re from? What was the funniest prank you ever saw in college? All of these will get you to the same answers, but in order to answer the question, they’ll have to think of a happy time, which will in turn, make them feel happy, which in turn, makes them happy to be around you!  We have all had wonderful and amazing things happen to us in life, yet rarely do we get asked about them or get to share those memories. Be the guy that asks fun questions!

The act of actively listening should go hand in hand with the first step of asking the right questions. When you ask one of these questions, take time to listen to what she has to say.  Don’t be thinking of your next question, or what to order, or when your new sneakers are supposed to arrive.  Be in the moment! 

Aside from the being polite and considerate, active listening will reveal a ton of clues about her and where to take the conversation next.  If you ask her about her favorite meal, listen for all the touchpoints you can use later: “Oh, man, well there was this time I was backpacking with my brother in Europe, and we were in Barcelona and had this octopus that was caught fresh earlier that day, and I can remember it tasting amazing!”

Don’t jump to a new topic or a new question, instead, delve deeper into her answer. There are so many things you can ask about now. Talk about brothers or siblings. Ask her where else she’s traveled. Does she speak any languages?  Is seafood her favorite food? Does she love the ocean? Even if you don’t have a follow-up question, it gives you the space to share about your favorite meal or that time you went to Spain or how fun your own siblings are. The simplest way to ask a positive follow-up question, regardless of the topic is to ask why she likes that certain thing. “Oh, you like playing tennis? So what do you like best about tennis that keeps you coming back and playing?”

Okay, so you arrive to your first date with a pocketful of questions to ask, but that’s only going to get you so far if you don’t have anything to add on your side.  A date (or any relationship) should be a rapport of back and forth energy. It can’t be one-sided.  

Make sure that you’ve got some stories of your own to share.  The simplest is to make sure you can answer any question you ask her, in case she needs a minute to think of any answer.  Also, stories are a great way for you to showcase all your best qualities and traits.

One of the things I teach my clients is “Never list. Always describe.” One is logical and one is emotional. Instead of saying, “I’m really spontaneous,” tell a story that illustrates your spontaneity. If you are a great cook, describe how you got into cooking or the story behind your favorite meal. Likewise when you discuss movies, websites, or music. Instead of listing your favorite bands/singers, say, “Like a lot of people, I have some varied tastes, but let me tell you about my favorite concert!”

There’s a reason for the phrase, “The man with the plan!”  Everybody loves a good plan!  It demonstrates leadership, confidence and shows your ability to adapt.  Now this goes further than the, “I dunno, what do you want to do?” thing.

I don’t want anyone to get bogged down in an overplanned date, but you should have a few options up your sleeve.  Yes, you may have asked her the type of food she likes and found a suitable restaurant, but what if the restaurant had to close?  Or they are short-staffed and the wait is too long, or there’s a COVID-19 scare?  You need to learn to be adaptable.

Aside from having a backup plan, you should have some possible options for the same night or later in the week.  If you’re meeting for drinks, find out where in your area you can have a fun night out at a bar.  If you know she likes music or art, come up with a couple of ideas to do for the date or weekend.  “I know you’re into art and next week is First Friday so I was thinking maybe we can grab a quick bite and check out some of the galleries. I found a cool exhibition on early Philly architecture and another one on ducks, as I know they’re your favorite animal!” Not only are you a man with a plan, but you also listen to her!

Body language is arguably the most important language that there is! When I’ve been in countries where I don’t speak the language, my nonverbal gestures and movements are the only language we have in common. Body language is a full and rich expression of the inner self with lots of clues and ways to emphasize your thoughts and feelings. 

First off, make sure your body language is open and welcoming. Don’t scowl, even if you’re trying to think of something. Don’t cross your arms or keep your hands in your pockets. I know it can be a nervous or self-protective measure, but it can come across as cold or uninterested. If you are listening to her, lean in and make eye contact. Make sure you smile a little when you speak.  If you feel a spark between the two of you, initiate light touching on her arms or hands.

While you are doing this, make sure you are watching her body language as well. Are her eyes glazing over as you tell your 10-minute-long baseball story? Is her body turned toward you or away from you? If she is playing with her hair or her necklace or adjusting her dress? That could be a good thing as we unconsciously groom/preen ourselves when interested in someone else. And obviously, if she’s constantly playing with her phone and semi-ignoring you, that’s probably not a good sign.

With the state of the world today, many single people are actively looking for healthy and loving relationships to enhance their lives. Let’s face it, we all spent a bit too much time alone during COVID-19 restrictions. People want to make connections, and they want to be impressed, so many first dates start by giving you the benefit of the doubt.  

I understand that a lot of our social muscles deteriorated in the past two years, so single guys may need to brush up a little before getting back out there. If you want to impress a woman, you’ll need to go a little bit outside your comfort zone sometimes. Try to be the most authentic you, and you’ll be surprised at the positive reactions you’ll get.