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!



Negotiating the First DATE – Set the Tone for A Successful Relationship

OK, so you’ve been contacted by someone online who has asked you out on a date… What now?

There are a few things to keep in mind that will help you navigate the first steps of the in-person part of this process.  I’ve laid them out below

1) What Kind of Date to Accept/Decline

-Coffee Date

Although this is common in the online dating world, I find a coffee date to be unacceptable.  It screams  “I’m cheap” and shows a lack of willingness to invest both money and a full evening or afternoon in getting to know you.  They can at the very least buy you lunch!

-“Let’s meet for a drink”

This one can go either way.  As I mentioned in my earlier post, if this is a same-day/same-night invitation, the answer is a very clear NO.

If you are going to accept this invitation, make sure it’s at least three days out, and make sure the time for meeting is between 6 and 7:30.  Yes, this is often an instance of “let-me-see-if-I-like-you-before-I-commit-to-a-whole-evening-out”; however, if it’s between 6 and 7:30 in the evening, if you are getting along, it will transition into dinner: a legitimate and 100% respectable 1st date. This is what you want.

If the drink is for 8 or 8:30, it could do either way; if the drink date is set for 9 or later, it is an indication that the expectation is either that you will have one drink and say “good night,” or  if you get along, the evening will turn into “drinks” which, having completely bypassed the formal indication of a “real” date (dinner), could be an easy segue into a night of intimacy, and likely a one-night-stand or a booty call at best.


Yes.  Scheduling a dinner means that a man is serious enough about finding a real relationship that he is willing to spend his time and money making sure that your initial contact fits the bill for an official date.  If you both choose to move forward in a relationship, it’s started off on the right foot.

This being said, there are a few parameters for what makes a dinner venue appropriate – or inappropriate.

Inappropriate vs. Appropiate Venues:

If you are a fan of “Sex and the City,” you may remember the initial date between Carrie and Big.  OK, so they slept together on the first date which is not usually a good idea but has not always ended in disaster.  After sex, however, he took her to dinner at a Scezhuan restaurant, where she ran into a friend who was on a date with a woman whom he later admitted he was embarrassed to date publicly.  She realized that Big was taking her to dinner at a place where he could take her out, while at the same time remaining anonymous.

This is a real thing.

You know the places.  I have many male friends who use online dating to hook up with women they would never date seriously.  Sometimes they take these women out to dinner first.  If the woman is one they would not date seriously, they choose the restaurant accordingly.  These venues typically are 1) close enough to their house (or your house) to make heading back to their place or yours “for a night cap” a reasonable and easy choice, and 2) somewhat under the radar (think: a place they would be very unlikely to run into anyone they know).

Make sure your date chooses a venue which is reasonably populated with people and not too dark or off the beaten path.  If your date is not comfortable taking you to a place where they might see someone they know, they may not have designs on a long-term partnership with you.  They may even already be in another relationship.


Although I am partial to dinner, lunch is a perfectly appropriate choice.  It’s a reasonable time and money commitment, and it certainly doesn’t indicate that they are trying to get you into bed and move on to the next.  Also, some people are not big drinkers, so lunch is a nice way to get the “official” nature of a first date in while not letting booze get into the picture.

2) Always Let Him Choose the Venue

The first reason for this is tied in to an assumption which I HOPE is true: YOU WILL NOT BE GOING “DUTCH.”  Please.  If a man is unwilling to pay for a first date, he is not worth dating at all.

Since he is paying, it would be presumptuous and inconsiderate of you to decide how much he is going to spend.  And if you have chosen the restaurant, it may indicate that you are at least willing to consider taking responsibility for the bill.  Nope.  You are not.

…But what if he asks you where you would like to go?  A very common question, and a good one!  If he asks you where you would prefer to go, offer a few suggestions, and be sure there are a few different options for how much the date will cost.  It is ideal to suggest two or three places with varying prices on the menu.  That way, if cost is a concern for your date, he can go online and review the menus to know what he can expect to pay.

And when you suggest options, don’t be obvious that you are giving him price options.  say something like, “Place A has a great outdoor patio, but Place B has great oysters – either would be great.”  You want to be conscious of the issue of money, but you don’t want to make a huge deal.  It’s a touchy subject.

Not all great men are flush with cash; but all men who are not flush with cash… don’t feel great about it.

You don’t want to put him in a position which might make him feel uncomfortable or overextended.  Remember: you want to really get to know him to see if he is a good match for you.  If he’s put in a place where he’s feeling defensive or resentful, you’re going to experience his quirks and not a nice, clean version of him.  We all have our quirks, but we don’t need to see them right away. We can get into all that later, once we’ve seen if we can enjoy one another’s company.

Another great thing about having him choose the venue is that it can reveal some pretty great information about him!  What is his taste like?  Is it compatible with yours?  Is he looking for a woman who dresses up, or one who wears jeans on a Friday night?  Does this fit with the kind of person you are?

This is all great, very useful information.  You don’t want to pass up the opportunity to learn!

Once your date is set, you can get ready for the first date!

I’ll check back in with tips on navigating that first date.

Don’t worry, it will be fun!





How to Get Started Right – Common Pitfalls

I have a few rules I’ve stuck to through my dating adventures online, and they have not failed me yet…

1) Setting Up Your Profile – Keep it Simple


Photos should be nice and not too made up.  You want them to be appealing enough to attract attention, but you DEFINITELY don’t want to post a photo that represents you as a more attractive person than will show up on the date (YOU).  The last thing you want is for the first feeling your date feels to be disappointment — talk about starting off on the wrong foot!  Your date will feel betrayed, insulted, and reluctant to believe anything you say going forward.  Not the best hole to dive into from the get go, and trying to claw your way out of that hole is, well, NOT CUTE.

You want to represent yourself in a good light, but we are also going for that added “Wow” factor when you show up to meet your date in person.  Leave a little room for improvement – meaning: Don’t only choose photos of yourself when you’re all dolled up with perfect hair and evening makeup.  Go ahead and include those photos, but also throw in some photos of you wearing jeans and flip flops, hanging out in a hooded sweatshirt.  It’s OK to show yourself all gussied up, but if you don’t also include images of you when you’re more casual (minimal makeup in an easy sundress), you’re not getting confirmation that your potential date would be interested in spending Sunday with you… instead of just Saturday night.

About ME

Again, keep it SIMPLE.  A few sentences is all you need.  You don’t want to give away too much, and it’s better to get to know someone naturally.  Unless you live and breathe your job, don’t mention it.  Just say a few things about how you see the world, some interests you have, or mention some of your values.

What makes you, YOU?

But again, be brief.

It’s a bizarre thing to have to summarize what you’re ALL about in a few paragraphs.  It’s way too limiting.  And if someone wants to get to know you, they should have to put in the time to learn about you — so don’t give them the Cliff’s Notes!

Also, you want to know if someone can see you in your true light.  If they meet you and don’t seem to “get” you at all, it doesn’t bode well for someone being a good match!  This is all good information for YOU to gather as you’re deciding if someone is a right for you.

2) Reaching Out

Personally, I never would.  For a few reasons, really.  Firstly, I think it screws up the dynamic in the beginning and makes me feel added pressure to impress.  It takes a lot of confidence to go after a man, and we have to be OK with rejection.  Rejection in other aspects of life can be easier to manage, but when it comes to matters of the heart, we can be extra vulnerable.  I simply know myself – and know that I’m way too sensitive to put my feelings on the line before I’ve received encouragement from the guy.

Also, I’m old-fashioned and I don’t want to send signals to any potential relationships that I don’t need to be treated like a lady.

This is me.

I understand that we’re all different.  If this is not you, and if your truest expression of yourself is being bold and going after the man you want, then that’s what you need to do.


3) Guys to Avoid

-Anyone who asks you to meet right away

Many men look at these dating websites as a way to order sex online, kind of like Chinese delivery.  Wanting to set up a “drink” or meeting somewhere right away is a good indication that this may be the case.

-Anyone who remarks on your appearance in an excessive way

“Wow, you’re really beautiful”/”OMG you are SEXY!”/”Gorgeous legs!”

They’re after ONE thing, and it’s not your multidimensional personality.

-Anyone who wants to know all your “stats” right off the bat

If they are asking you what you do for work right away, a few things could be at work here:

1) They are looking to pigeonhole you into a type.  This typically comes from men who are not looking to get to know all the layers of someone and are likely going to be judgmental; OR they are simply looking for someone to fits an idea they have about what would work well with what is the center of their universe: their own life.  These questions might seem benign at first, but they likely wouldn’t come from someone who’s looking for a real connection.

2) They could be, well, boring!  My dad once told me (when I was about seven years old, mind you.  Planting the seeds early) that if anyone ever asked me, “Do you come here often?” that I should walk away and rebuff any further advances from whichever individual uttered those words to me.  Not because they were predatory or because he never wanted me to get picked up at a bar, but because that was the least creative pickup line in the world, and I should never deign to date anyone who was so sorely lacking in imagination and intelligence.  “What do you do” falls under that category for me.

-Anyone who is rude or overtly sexual

I probably don’t need to elaborate on anything here, but you’d be surprised at how many people behave this way online – and how many women respond to it.

How to Handle Online Communications Before the Date

Be Nice and Polite, but Also.. REAL

Think of the conversations you have online as though you are at a dinner party and have just been seated next to someone at the table.  You would be friendly and upbeat, and unlikely to hash out stories of a stressful week.  You’d be pleasant, and ask interesting questions to get to know them and make them feel comfortable.  This is how you should be when you are “meeting” them in cyberspace.  If you were at a party, you’d likely want people to have a good impression of you and recall the time they spent with you fondly.

No different here.

The slight difference here, though, is that you are looking at them as a potential partner.  Because of this, you want to make sure they get a taste of the authentic you.  You can be pleasant without being a pushover, and you can state your opinions without being controversial.  If you stifle your own personality, neither you nor your potential date will have any idea as to whether or not you will be a good match.

Before you enter a relationship, you need to make sure there is space for you in it.  This is a continual discipline, and it starts with initial conversations you share.

Don’t Talk Too Much Online Before Meeting

Any bond you create without meeting someone is really just an illusion.

Yes, you want to get an idea about whether or not you may be a good fit with this person (and they, of course, want to get an idea of that as well); however, all you need to find out before meeting them is whether or not they are worth meeting.  Any ideas you may form about who they are on a deeper level aren’t reliable – you have to spend time in person to find those things out.

Also, any information you get or give before having a true interaction with someone is subject to being fleshed out in fantasy.  Say, you’re speaking with someone who works in finance.  You may get the idea that they are wealthy and adventurous; but in reality, they may be struggling and not happy in their work, perhaps enjoy a few too many martinis on a nightly basis.  Or say you are talking with someone who works in Reality TV.  You may think they are shallow and not good husband material… but as you get to know them, you realize that they are a passionate artist who simply made a practical choice in life but loves going to the Opera.  You never know.

And they are likely doing this with you.  They learn you are an accountant and may draw the conclusion that you are boring and then decide not to meet you.  And they won’t ever get to know the fun, adventurous side of your personality.

Also, you don’t really know if you have that chemistry with someone until you meet them.  If you don’t have chemistry with someone, then there’s really no point.  I once dated someone who was everything I’d ever want.  Funny, sweet, successful, handsome, and we got along so well… but our chemistry was off.  Every time I kissed him, it felt like I was kissing my brother!  It was horrible.  On paper, in pictures, and on the phone, he was my dream man.  But in person, it just didn’t work.

Keep these tips in mind, and I’m sure you’ll be off to a great start.

I’ll post again with more advice for what will come next: your first date!




Coming Around To Online Dating – Finding Love on my Iphone

I’ve long been averse to anything resembling online dating – for a few different reasons, really.  The main reason, however, is that I have always been reluctant to give anyone an impression that I am single… NOT by choice.  In my fantasy of how I want people to see me, I am single by conscious choice (and LOVING it, of course); and the moment (and I mean the EXACT moment) I decide I want love in my life, I finally acquiesce to one of my many suitors who has long been pining for me and patiently waiting for me to come around.

Sound familiar? ;)

There was always something that felt desperate about advertising that I was looking for romance and did not have it at my fingertips.  I also didn’t want people in my circle to know that I was looking.  I felt like it was giving too much of my power away.  I felt vulnerable and was a challenge for my ego.

But, as with any struggle that is ego-based, I eventually worked my way out of that point of view.  I’ve now found that online dating has been fun, informative, and a wonderful learning experience.

I’ve also learned to be comfortable with the fact that I am wanting a relationship that I don’t yet have.  I no longer feel desperate; I simply have accepted that, as a complex adult with many distinctive qualities and preferences, it’s only natural that it should take a while for me to find someone who is a good fit.

And there’s nothing wrong with the fact that it hasn’t happened instantaneously for me.  If we’re all truly being ourselves and honoring our own spirits as individuals, it’s only natural that our true, honest selves will not fit with just anyone.  The only way we could all fit with just anyone is if we were stifling our needs in order to be easy and amenable.  This is no way to live.

If you can’t be yourself, what’s the point?

There’s an exquisite loneliness that comes from feeling alone when you are with someone.  I believe that loneliness comes from not being able to fully express ourselves.  This is what daily life is like when you are with someone who is not a good fit.  You can never have a true honest moment.  And this, my friends, is exhausting.  And this is what it feels like to be with someone who IS NOT a good fit.

You know the feeling when you hear something said by another person that really resonates with you?  And how wonderful it feels to feel in synch with how someone else’s thoughts?  What’s happening in these honest moments is the experience of two individuals being completely themselves while in the company of another. There’s nothing like it!  And this, my friends, is what it feels like to be with someone who IS a good fit!

Once I embraced this idea, it was so easy to let go of worrying about anybody else thought of my life, or my choices.  My ego worrying about how desperate I may appear to others – it just seems pathetic and such teeny tiny potatoes when compared to an honest quest for something so important: authentic, true love and a healthy partnership.

This paradigm shift has transformed online dating into a very useful tool I am grateful to have at my disposal.

I encourage everyone who is looking for love to embrace the process, and to do so proudly.

I will come back soon with some lessons I’ve learned that I hope you will find helpful as you embark on the journey of love online.

Best Wishes. xx


Welcome all!

Thank you for visiting my site!  I look forward to sharing my thoughts and experiences with you on my quest to know myself better.

I am a single woman in my thirties (think: Sex and the City), looking for love and on a quest to live my best life.

I enjoy learning about what makes people tick, learning about what makes ME tick, health and fitness, great champagne, New Yorker Cartoons, and people with good taste, just to name a few!

I read somewhere that the purpose of life is to know oneself, so I’ve decided I’m going to try that one on for a while and see how it fits.

Life takes unexpected turns and is always full of surprises.  I hope to learn from each and every one of those surprises.

And I intend to chronicle that journey with you fine people.

Cyber hugs and cyber kisses,