When my son left for college this fall, I decided it was time to consider the possibility of dating again.

I made this decision because I’m lonely (I know it’s very unfashionable to admit this); whenever I see cute couples walking down the street holding hands I find myself tempted to run them off the road with my car; and my most compelling reason, I don’t want to die alone.

I’d been so busy working full-time, raising my son as a single parent, and going to school that I just didn’t have time to give dating much serious consideration, but when I found myself alone after so many years of controlled chaos I realized that I had a choice—I could passively allow life to happen to me (i.e., gain 50 lbs. while laying on the couch watching BravoTV), or I could take proactive control of my life by grabbing the proverbial bull by the horns, and carefully and considerately, craft the life I want to live.

And since I am petrified that the inevitability posed by Nora Ephron’s character Harry to his new friend Sally, (When Harry Met Sally) may actually be my reality:

“Suppose nothing happens to you. Suppose you lived out your whole life and nothing happens, you never meet anybody, you never become anything, and finally you die in one of those New York [aka Chicago] deaths which nobody notices for two weeks until the smell drifts into the hallway,”

I decided to take the plunge that millions of other adults in midlife are taking, and I joined Match.com.

To be honest, I wasn’t really sure what I wanted. While it’s true that I didn’t want to die alone, I also didn’t necessarily want to get married again.

Believing another famous Ephron quote, “the desire to get married is a basic and primal instinct in women. It’s followed by another basic and primal instinct: the desire to be single again,” I decided to start off slowly with almost no expectations, put a profile up online, and just see where things led.

I was actually (and naively) excited about the prospects of dating again because I felt as though at this point in my life, I kind of had it all together. I looked pretty good for my age (or so my friends told me), my career was going well, I was relatively financially secure and I had far more wisdom than I had the last time around (or so I thought).

So, I dove in with gusto, determined to have fun, and ultimately find a date. And, maybe, if the universe was on my side, dare I say, a boyfriend.

That was then. This is now.

The purpose of this article is to help my fellow singles navigate the world of online dating, and hopefully help them avoid some of the pitfalls I fell in (face first). Perhaps together we can gain a better understanding of this new era in dating, which I can assure you does not at all resemble the dating world of my, and I’m guessing your, youth.

Online Dating: A Whole New World.

First, and foremost, there are virtually no similarities between online dating and normal dating.

In online dating, someone parachutes into your life without any context, which means they can just as easily parachute right on out. You have a great few dates, you’re thinking about inviting them to that upcoming family wedding, and then you never hear from them again.

Or, after a few seemingly great dates (and a few passionate kisses) you get that uncomfortable text, like the one I recently received:

“I had a really great time tonight” [me too!].

“But I don’t think there’s a spark and I’ve met someone else I think I’m more compatible with” [What? In two hours??].

Which leads me to my next observation about online dating: parallel dating.

In normal/real-world dating, parallel dating—otherwise known as “serial dating”— was the stuff of scumbags and while relationships weren’t necessarily born on the first date, one didn’t really need to worry too much about dating a man (or a woman) who was at the same time dating two, three or even five other people.

Imagine being in a bar and seeing a man troll from woman to woman with the exact same pick-up line. By the time he got to you, you’d likely throw your drink in his face and tell him to go to hell.

Yet, in the online dating world, parallel dating is not only permissible, it’s encouraged! Send an email to someone on Match.com and you get a pop-up message stating, “If you like CuteMan1, we think you’ll really like Cuteman2!”

Imagine!

Men (and women) can now date as if they were car shopping. It could sound something like this, “I like you very much, but I’m sorry, a new shinier model just drove onto the lot that I feel compelled and am actually being encouraged to check out.”

I’ve also heard this dynamic referred to as online fishing—where the man (or woman) throws out a giant net—let’s say, 10 emails a day (sometimes the same email), playing the odds. If Match.com says that 10% of people will respond to your email, and if you send out 10 emails a day, then that means you’ll receive one response per day, seven per week, 30 per month. Now, those are some pretty impressive odds!

Parallel communicating and parallel dating seem to be a normative part of the new online dating ritual, which begs the question of what impact this dynamic has on real, live dating. At what point is it no longer okay to keep shopping/fishing?

When I first began online dating I was a veritable naïve fool.

I felt guilty engaging in an email exchange or texting with more than one man at a time. I also felt guilty communicating with someone regularly, or even dating him, and then going online to look at more profiles.

What if he saw me? What would he think? Maybe if he didn’t call again it’s because his feelings were hurt that I came home and went right back on Match. And yet this also begs the question of what he was doing online (checking out my profile perhaps?).

Even though I wasn’t serious with any of these men, it felt disingenuous to communicate with more than one at a time.

But apparently, I’m just about the only person in the online dating world who felt this way, because at least early parallel dating, and certainly parallel communication is the name of the game online (and yes, I do know that those men I was dating weren’t online five seconds after our date checking out my profile—I’m not that naïve).

So, I succumbed, and I also failed. Miserably. Apparently my middle-aged memory just isn’t what it used to be. I began mixing up names, and I could never remember what I’d said to whom. So I learned quickly to start every sentence with “I may have already told you this, John, er I mean Mike, no Dave…but this really funny thing happened to me.”

Ready, Set, Go! Oh wait, No…

I’ve had some really great dates, and some not-so-great dates. Timing and balance seem to be key. Date #3 seems to be the killer—the yes, we’re a go, or no, we’re not.

This is unfortunate because I often can’t decide about someone that quickly as I tend to emerge rather slowly—both in the emerging of my personality, and in my feelings and affection for someone.

If I really like someone then daily calls may feel comfortable, but if I’m still on the fence, then having someone I’ve gone out with only a few times call me every day can seem like an intrusion, but that may change on Date #7, if we get there.

Also, I’ve learned to be very wary of the “recently-broken-up” date, and now come right out and ask how long someone has been single before they went on Match.com.

It seems to be the norm these days to merely hide one’s profile while in a relationship, only to unhide it the moment a bump in the road is encountered, or when a squabble causes a temporary disruption in the relationship.

My message to couples in a fight: remember that unhiding your profile and having a few dates with someone only to hide your profile again when the fight is resolved may work well for you, in that you won’t have to endure a solid week of loneliness, but it sucks for that person who dates you in the interim and actually thinks there’s potential for longevity (i.e., a second date).

Unfortunately though, I have found that online dating, while at times effective and expedient, also encourages a shopping cart-like mentality where people don’t have to make a commitment (supply and demand), and find it far too easy to put their best foot forward in a way that masks their authenticity, and what Anita Moorjani (Dying to be Me) calls, our unique magnificence—our personal uniqueness that only we have, and that emanates when we’re just being ourselves, and aren’t trying to impress others or manage what others think of us.

Fortunately, I believe that there are many really good people online who have the best of intentions and really want to find that special someone.

Love elephant and want to go steady?

Sign up for our (curated) daily and weekly newsletters!

Editorial Apprentice: Brandie Smith/Editor: Renée Picard

Photo(s): bixentro/Flickr Creative Commons; Don Hankins/Flickr Creative Commons