Your First Date – How to Make it Work For You

Alright, so now you’ve accepted an invitation to meet… What next?

What to Wear

-What is Appropriate for the Venue?

Clearly, this will inform your outfit choice more than any other factor.  Obviously, if you’re meeting for lunch at a casual restaurant, flip flops and a sundress will be fine; however, if you’re meeting for lunch in a business district, something business casual will work.

The same applies for dinner.  Just use common sense and make sure that your attire is appropriate for the neighborhood, time of day, etc…  Just make sure you are appropriate.

-Dress Down a Little

Of course don’t try and look like a slob, but be more conservative in your dress.  If you know you can dress or do your hair a certain way that makes you look like a million bucks, save that for later.  You want to make sure your date is interested in you for the RIGHT reasons.  We are, after all, looking for someone who will love us even when we’re out on a hike.

If he’s worth it, you can dress up and show him your best look once he’s proven himself to like you for who you ARE, not what you look like when you’re all done up.

So on your first date – and, of course, if it is appropriate to do so at the venue – maybe don’t wear a dress, but instead wear jeans, a nice top, and heels.  Save the dress to impress him after a few meetings, should he make it that far.

-Only Show One Asset at a Time… if at All

I have a general rule that I like to stick with, which is a good rule of thumb in general for ladies: ONE ASSET AT A TIME

If you are going to wear a low-cut top that shows a little cleavage, wear pants or a longer skirt; If you are going to wear something on the shorter side to show off your legs, cover up up top!

It looks desperate to have everything hanging out all at once.  Low cut top AND a short skirt?  It’s too much!  It indicates that you are placing all of your value on your sex appeal.  Your sex appeal is a wonderful thing, and is meant to be enjoyed; but if you let it dominate, you are advertising to the world that you don’t think WHO YOU ARE is as important as HOW YOU LOOK.

Also, it’s just kind of tacky in my opinion.

So, since this is your first date and you want to leave a little to the imagination, perhaps not showing ANY of your assets is a good idea.  Let him focus on your face.  He can be invited to revel in your sexuality later on, but you don’t want to start there.

How to Behave


The most important thing is to make sure you are being authentically yourself.  There’s nobody else like you, so let your true self shine!  Also, if you’re looking for a real relationship, you need to find one that you can be yourself in, so make sure that you ARE yourself from the get go.

-Find Out About Him

The same way that he is interviewing you to find out if you are a good fit, you are also interviewing HIM.  Don’t just hope that he likes you, see if you like him.  Don’t let the fear of rejection or the anxiety that comes with wanting someone to like you get in the way of your greater goal.  As much as it may feel like one, this is not a one-sided audition.  Don’t give away your power just because you want to be liked.  We all do, but being authentic is more important.


Also, in a world where so many people are all about themselves, it’s a wonderful thing to spend time with someone who’s a good listener.  Not only will you find out more about him, you will likely stand out from the crowd!

-Don’t Put Too Much Pressure on THE DATE

It’s easy to get worked up about a date.  Many of my friends get excited beforehand, and if it goes well, they get even more excited.  They let their minds wander into picturing a life with someone after one good date.

But that’s all fantasy.

Even if you are having a good time, you can’t be sure of his experience, let alone whatever else might be going on in his life.  Recent ex-girlfriends or other women he may be seeing, unresolved issues, work… there’s no way to know what else may be affecting his sate of mind – and you’ll make yourself crazy if for one minute you let yourself believe that you can figure it out.

Sometimes, after what we feel is a great first date, people drop away.  We don’t know why and we can’t know why.  So just keep it moving.  Enjoy the date and then move on.  Focus on yourself, stay open to other invitations.  If he likes you and genuinely wants to pursue something, he will.

-Stay Open To Other Possibilities for the Relationship

Another way to relieve a little pressure you may put on yourself and relax your expectations is to stay open to other possibilities that this meeting may hold for you.

Sometimes, you meet someone and realize that your chemistry is off.  Well, this my be the lazy part of me talking, but if you’ve put for the effort to set aside an evening, pick out an outfit, and forgo other plans (which may have included catching up on your DVR recordings – and that’s OK), then there’s no need to declare the evening a failure just because it wasn’t a love connection.

This person may end up being a potential friend or business contact.  Or perhaps you remain in casual contact and end up meeting someone great through them!

You never know.

And let’s face it, it’s a small world – you’ll likely run into them again or have some friends in common, if not currently, then at some point down the road.

I typically walk into a date the same way I walk into meeting with someone who is a potential business client.  I’m friendly and open, and I simply enjoy taking the time to get to know them and find something I like about them or a common interest we may have.

Or perhaps you can imagine you are meeting a friend of a friend who’s new in town and looking to meet people.  Naturally, you’d be friendly and look for common interests, try to learn about them… and let’s be real, you’d probably be open to a possible love connection, right?

Shifting the focus and relieving the pressure we tend to feel because you’re on a “first date” can really help you to feel more comfortable, be more natural, and let your true personality shine through.

When Saying Good Night

-Be Gracious

Whether or not there is a love connection, it was nice of your date to make the effort and take the time to take you out.  Say thank you!  Just keep it simple.

-A Goodnight Kiss?

You have to do what feel right for you, but a kiss is not necessary.  I typically don’t kiss on the first date, not because I’m withholding, but simply because it doesn’t feel natural when I’ve only met someone once.

Again, you don’t really know what he thinks of you, and you won’t know if he’s interested in getting to know you more unless he asks you out on another date.  If it’s not a love connection and you don’t go out again, then if you run into him later and you HAVEN’T kissed, then it’s a lot easier to be comfortable with him, and be pleasant and friendly.

Be sparing with your intimacy.  The last thing you want is to have your neighborhood haunted by old dates and reminders of feeling rejected.  As women, we can be hurtful to feel like someone is not interested, particularly if we’ve shared any degree of intimacy with him – and a kiss certainly counts.

There’s nothing wrong with being sensitive if you are, just respect that sensitivity and proceed accordingly.

Wishing you luck out there.  Happy dating!



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