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!




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