What to Do on a First Date

Beauty portrait

Previously, I wrote about how to plan a date and a woman’s mindset on a first date.  Today, I’m revealing all my best tips for the date itself.  With a little bit of practice, you can master first dates.

Here’s how:

  • Greeting her.  How you greet her is up to you – a kiss on the cheek, a slow hug – but two things are not negotiable:  a sly smile and steady eye contact.  This communicates that you’re relaxed, comfortable, friendly and not intimidated.  The opening moments are crucial, and you can get off to a good start immediately.
  • Move slowly.  This sounds strange, but the opening moments of a date are often filled with a quick, nervous energy that feeds on itself.  Walk slowly, relaxed and confident, as you approach her.  Speak slowly.  Show her physically that you’re not nervous (even if you are), and that there’s no reason for her to fear awkwardness.
  • Take the leadership role early.  After you hug her or kiss her cheek, gently (almost imperceptibly) put your hand on her lower back and guide her toward the next location (the seat, the bar, the venue, etc.).  This communicates that you’re the host for tonight and, without being demanding, communicates that she can relax and go along for the ride, free to focus on nothing but the two of you.
  • Sit side by side.  Thanks to your planning of this date, you’ve already chosen a place where you’re sitting side by side or diagonally.  Use this to create incidental touching throughout the date:  fist bumps, ironic high fives, touching her elbow with the back of your hand when you both laugh about something.  These things create a physical intimacy that later will pay off when you kiss her.
  • Have two stories ready for the first conversation.  Her biggest fear is awkwardness, and the biggest awkwardness is that there’s nothing to talk about.  You’re going to eliminate that fear by immediately, upon sitting down together, using your storytelling skills to tell her a personal story for a couple minutes. This is perfect because she can relax, not worry about what to say, and simply study you.  And, because it’s your own personal story, you know that her first impression of you will be a good one.  If the first one doesn’t lead into a conversation, have a second one ready.
  • Avoid standard conversation topics.  When I wrote about banter, I wrote about how important it is to avoid boring, standard topics. On your first date, avoid asking each other (and telling each other) basic facts about your life.  Don’t discuss your job, your family, where you grew up, how many brothers and sisters you each have, etc.  These are things she’s talked about to every guy she’s ever dated. Be different. Be more fun. Use your banter skills and storytelling skills to have a good time.  Even if she asks you what you do for a living, especially at the beginning of the date, you can always playfully redirect the conversation with a smile:  “Let’s talk about something fun and outside of work:  what’s the coolest thing you’ve done this year?”  Most times, she’ll appreciate this, because she didn’t really care about the answer and was just trying to make conversation.
  • Have a handful of stories.  Whenever conversation dies down, tell another personal story.  You’re just guaranteed that the conversation never runs out.
  • Transition to Dating Talk.  Once the conversation feels comfortable – you’ve both told some stories, you’ve both been having fun for a bit and the nervous energy is gone – you’ll want to transition to what I call “Dating Talk”.  Ask her, “What are three qualities you look for in a guy you hang out with?”  This signifies to her that it’s time to talk about dating things.  It changes the mood and (if you’ve done everything right up until now) creates a mood for kissing.
  • Kiss her as a reward.  Women dream of an attractive guy liking them for who they really are.  Give her this experience.  Once you’re into the Dating Talk, wait until she says something that you like (funny, honest, smart, etc.).  Then kiss her as a reward for being awesome.
  • Be confident about the kiss.  Since you’re already sitting side by side and have been touching incidentally, the kiss is not a huge departure.  Simply look her in the eye, look down at her lips, look back in her eyes, and say, “That makes me want to kiss you.”  Assuming she does not suddenly have a horrified look on her face, gently put a finger under her chin to guide her face toward you.  Kiss her lightly – don’t start making out immediately.
  • Break off the kiss. Once you’ve kissed her a bit, stop.  This shows her that you’re not solely interested in physical intimacy.
  • How to know she’s ready to be kissed. My father was a genuine Casanova. He told me the sure fire way to understand if or not to attempt a first kiss, and how to make it work. If and when things are going well…lots of eye contact, smiles, and a relaxed atmosphere…notice when your date’s hands are relaxed and accessible. This will work best if you use your hand farthest away from her, and her hand farthest from you. So when the right opportunity presents itself, gently slip your hand into hers.  If she closes her hand around yours, you’re half way home as she’s just given you the green light. Raise her hand to your lips and kiss the back of her hand while looking her in the eyes. Turn her hand over and kiss the palm while closing your eyes. Then while still holding her hand, gently guide her towards you and kiss her on the lips. If things work out well she’ll be smiling while the maneuver is being conducted, and will remember you for this for a long time to come.
  • Mix it up.  You’re now most of the way home. Spend the rest of the date alternating between fun banter, storytelling, and making out.  Whenever you go too far into one, move to the next.
  • Do not sleep with her.  This might sound strange, but I don’t recommend sleeping with a woman on a first date, even if she’s amenable.  I recommend stopping at making out and resisting anything sexual. It gives you both something to think about for future dates.  In my life I have routinely resisted sex on first dates.
  • Make sure she gets home okay.  Make sure she gets inside her home (if you’re dropping her off), inside a cab (if you’re in a city), or inside her car sober (if she’s driving).  It’s the right thing to do.

With this guide, and a little practice, you should find that almost every date goes smoothly and has a chance for the two of you to connect.