Returning to Dating After a Long Absence
Coming back to dating after a long time of being off the market
can be intimidating and scary. But don’t panic — what you already
know is relevant. Some things have changed, some haven’t, but no
matter how you slice it, it’s people meeting people. It’s still about
you looking to find someone you like.
If, while you were away from dating, you did any kind of marketing
or sales, any sort of product presentations, or had to make pitches
of any type, you’ve already got an edge in this process.
Now you’re the product. Your job is to show yourself in the best
possible light. You’ll need to present yourself with your target
audience — your dating pool — in mind.
But this is the good kind of product promotion, where
you’re looking for a match that actually works, not the kind where
you push something on someone they can’t use. You want to present
yourself truthfully so that if someone does give you a try, they’re
giving you a try, not a fantasy. You at your best, of course.
Turn on the soft lights and spell check
We want your best side here, using the most flattering light. No
product is flawless, no purchase without risks, so your job isn’t to
tell the potential buyer everything that could go wrong, but to offer
a window onto what could go right. The upside of you, the advantages.
Selling yourself is hard, though, isn’t it? If you’ve been through
a bad breakup or divorce, you might be feeling down, or fragile, and
it could be hard to identify your best features. Ask those friends
who like you to help you with this. Ask family who is supportive.
(Flirting Arts services also include personal coaching.)
Just as you try in person to present yourself well, with good
grooming and posture, online you want to show good pictures, use
correct language, and select upbeat words. It doesn’t have to be
perfect — you probably aren’t — but take you best side.
Where are the fish these days?
So where are all those possible dates? And how do you find them?
There are just where they used to be in the old days; there are
singles groups, classes to take, volunteer opportunities, various
clubs, and yes, even bars. People meet whereever they gather, and
there’s a lot to be said for checking someone out across a crowded
room to get a sense for them and talking to someone to pick up all
those important, subtle non-verbal clues.
But there’s also the online world, to find people you might not
otherwise stumble across by accident.
Introducing yourself to strangers and making conversation is both
a skill and a challenge. It’s one of our favorite subjects, here at
Flirting Arts, and we teach classes on how to do this and can also
help one-on-one, remotely over the net or in person if you’re in
Seattle, Washington. We love this subject.
Back to you. We suggest you take a two-prong approach to dating:
get out in the physical world and
use the Internet.
Welcome to on-line dating
More and more newly minted singles are showing up on-line every
day. Ten years ago online dating was mostly about the 20 and 30
somethings, the early adopters. Today there are folks from every age
range possible. Whatever age you are, whatever range you’re looking
for, people in your dating pool are online looking, too.
Online dating services come in many types. There are free and paid
matching sites, there are online singles forums, there are chat
groups. And the people who you can find on-line can be highly
compatible folks who you’d never meet in your existing social
The are many advantages to online dating. It can be very low
overhead, letting you skim many profiles, and use email to select the
people who most seem compatible. It can be easy to get started and
it’s a great way to select from a large set of diverse people you
might not otherwise meet, and to save you the cost of gas and the
price of coffee.
But don’t mistake that for meeting people in person. Think of the
online process as screening for an in-person meeting.
But I am a dog!
There’s an old saying among the earliest pioneers of the Internet:
“on the net, no one knows you’re a dog.” What we meant by
this is that if you can’t see someone in person, you really have no idea
who or what they are, no matter how they present themselves. Anyone
can write anything, and photos can be old, modified, or stolen.
When I say show your best side, I don’t mean put up a picture of
someone else — or you 100 pounds ago. I don’t mean copy someone
else’s profile or lie about yourself. But a surprising amount of
people do this online, people who are unclear on the concept of
dating online in order to meet and develop a real and geninue
relationship, not one based on pretense and deceptions.
Keep your personal information private. Your name, address, other
identifying information. But be open about your real interests and
flaws if you want to attract people who like who you actually are.
It’s okay if you’re a dog. Be the best dog you can.
We see what we want to see
There are many pitfalls in online dating. More common than
outright lies are people or people who stretch their presentation
beyond a reasonable flattering light is us tripping ourselves
up, projecting onto someone our own desires, filling in the gaps with
wishful thinking. Whether it’s their fault or yours doesn’t really
matter. Practice no-fault online dating! The fact is, when we’re
online, there’s so much we can’t know that we see what we want to
see. If you connect with someone online who seems fabulous and
incredible, the chances are very good that they aren’t all that. How
to find out?
Meet in person before the fantasies take over
The moment you’re jazzed, the moment you’re starting to send extra
emails, to feel tingly and excited when they write you back, you’re
hooked. At that point, you should talk on the phone and plan an
in-person meeting to find out if there’s real potential. A compelling
profile, a fabulously attractive photo, and intriguing and inspiring
email does not tell you how a person speaks, stands, walks, or
smells. Their profile might have been written a long time ago, or
maybe they are still using their high school photo. Maybe they really
did stop smoking but have started up again and just forgot to mention
Even the sincerely written profiles have gaps and open spaces —
it’s just a sketch, after all. The discrepancies are rarely
intentionally deceitful, but the difference between how someone seems
to you online — either because of their profile or your own hopes —
and how they come across in person can be amazing and astonishing.
And not always in a positive way.
Take the online world with a large grain of salt.
On the Internet, no one knows you’re a serial
I’m not trying to scare you, but especially if you’re a woman, you
need to be careful. You’re smaller than the men you’re likely to
meet, so you shouldn’t meet them in private or in an isolated
location. Bad men (and yes, alas, it mostly is men) can be
well-spoken, well-written, charming and persuasive. No matter how
reasonable they seem, no matter how much they pressure you —
especially if they pressure you — stay safe, stay cautious.
It’s not hard: meet at a cafe or restaurant, park in a well-lit
area, and if you have any sense you’re being followed or the guy
isn’t safe, don’t go to your car and don’t go somewhere isolated.
Call a friend from a public location, or ask someone at the cafe to
walk you to your car.
If it doesn’t feel right, don’t do it. Trust your intuition.
To be clear, in over 30 years of online dating, with hundreds of
first dates from online contacts, I have never had a problem, and I
have never felt that I was in danger. But I always practiced this
sort of caution, and any guy who pushed me in email to take chances
in our first meeting didn’t get one.
Also I never give our my full name, address, or phone number (if
it can be traced back to me) to anyone I have only met online through
a dating site. I take my time and usually only give this information
after I know more about them or have at least met them in person and
have given my gut a chance to weigh in on how much I trust the guy.
Is my instinct perfect? No, of course, not. But no matter how
charming or persuasive a guy is, he’s still stronger than you and
he’s someone you don’t know.
When someone online asks you for personal information, starts
demanding favors, or starts trying to act as if you’re already in a
relationship with them, imagine that they are a stranger in a dark
alley, who you can’t see, with a voice you don’t recognize. Because
that’s really as much as you know about them.
And guys? It’s not fair that you’re stronger than we girls are,
but a lot of things aren’t fair. It’s up to you to be respectful of
boundaries, and understand about the dangers that women face in
dating. Be gracious, open, and up-front and you’ll go far with the
sort of women who care enough about themselves to be cautious.
Optimism tinged with Caution
The best way to approach online dating is with optimism tinged
with caution. It’s easy to imagine the worst, but it’s also pretty
easy to imagine the best, especially when you see a really cute
potential person. I’ve met dates who were far more attractive in
person than their pictures implied, so it’s possible to be pleasantly
surprised. I’ve met guys who were stunningly handsome online and in
person, but dumb as bricks, which is a non-starter for me. Only you
know what you really want, and you should look for the possibility-of
it, not the certainty, in every online encounter.
I’ve met some of the most important people in my life online, and
I’ve had some fabulous dates and relationships as a consequence of
online matching sites. I started lasting friendships, made business
contacts (yes), and met fascinating people I would never otherwise
have met. It can and does work.
But all types are present online and many of them fake very very
well. Be careful about online only contacts who act as if they’re old
friends or new lovers. It’s not (yet) a relationship just because
you’re engaging each other’s fantasies, not unless online is where
you’re truly intending to keep it, forever. Because when you
transition to the flesh, things are very different.
The fantasy-only dating game
There are people who date online who don’t want to meet you in the
flesh, ever, no matter how well you seem to hit it off with them. Why
not? Maybe they’re scared, maybe they’ve been burned, maybe they
prefer fantasy to flesh, maybe they’re nothing like what they’re
presenting online. Whatever the reason, there are people who are
happy to keep going with hot and promising email but will never meet
you in person. Just be aware of this, and if virtual relationships or
“sexting” is not your thing, call their hand as soon as you
feel the tingle. If they keep putting you off, cut your losses.
Unless, of course, you’re interested in the fantasy dating game
yourself. In which case, say so as soon as you reasonably can. Ask
for what you want and you’re more likely to get it.
Ready, set, go!
If you’re hesitant about online dating – and you are, aren’t
you? – it’s important to find a way to get your feet wet as easily
and painlessly as possible. I recommend using a free service because
for most people it’s easier to try something when they don’t have
money invested. Some pay services are not expensive, but it’s a
psychological barrier, so I suggest you start with the free services.
Remember, your time is not free. If a service doesn’t suit you, don’t
use it, whether it’s free or not.
Where to start?
Contrary to what you might expect, the pay services aren’t
necessarily better quality. They do give you access to people who are
also willing to pay for such services, but that doesn’t make those
people of better quality. There are plenty of great potential dates
on the free services as well — including people who are gainfully
employed. The Internet began with a cultural assumption of free
access, and a lot of people who were there at the start, now in their
50s and 60s and well-employed (or retired) are more at home on the
Despite having been recently bought by Match.com, I recommend
Okcupid to newcomers. It’s easy to get started with and has few
requirements. It asks sometimes absurd and useless questions, but
some of them are relevant and entertaining, and there are ways to
Focus on what you really care about. If what side of the bed you
sleep on isn’t really high on your list of criteria, skip that
question. By the same token, if you want to have kids, don’t bother
with potential dates who say they don’t.
Give a false name if it makes you more comfortable – you can
always trash the profile and start over. Look at other profiles,
especially those of people who are the same gender/orientation/age to
see how others like you are presenting themselves.
Start simply, with the basics. Look around. Add onto your profile
regularly. Remember, the goal here is to sketch yourself in a good
and positive light, while still saying what’s true. Write to other
people whose profiles you like. Short and sweet, with something
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