The Pros and Perils of Online Dating

This post was published on the now-closed HuffPost Contributor platform. Contributors control their own work and posted freely to our site. If you need to flag this entry as abusive, send us an email.

When I got divorced at age 37, I'd never really dated. I'd met my husband at age 20, and in the five years before that I was basically serially monogamous with various men/boys I met through school. I'd never been set up, never gone home with a guy from a bar, never been asked out really, or been in the position of wondering if he'd call, wondering if I should make a move.

All that stuff was foreign to me, so I was pretty pysched to experience it. The idea of going to restaurants with handsome, interesting men, of flirting, of liking someone new. All very exciting! I spread the word, sent emails to friends and acquaintances I thought might know interesting men to pair me with, and started exploring the myriad online options.

What I found is that while set-ups were objectively more successful (over a two year period, of the 5 set-ups I went out on, we had a 100% success rate in terms of one date leading to two or three, maybe even sex), and the online dates were usually a categorical failure (maybe 5 of the 30 men I met during that same period, I saw more than once), overall I thought online was maybe the better course. At least for certain reasons:

With set-ups you have the tricky issue of dealing with the person who set you up after it all goes to shit. The poor well-intentioned friend inevitably gets caught in the middle. Either you've disappointed someone or behaved badly, or he has. Either way, there's usually some collateral damage, and it's awkward.

While it's true that the people you meet through set-ups are more likely to share your educational and socio-economic background, or be from "your world," and that can be an initial relief, I found that it still doesn't mean you'll connect, or ultimately even like the person. Think of all those dads you know at your kids' school -- how many of them do you want to sleep with? Not many, I'm sure. Connection's a mysterious thing.

So I'm a big fan of going online to troll for romance. Here's why, and this is what I tell all my recently single friends:

1. It's great practice. If you haven't been out there in awhile, or if like me, you've never dated, there's a huge learning curve. Having a dozen coffee or drink dates with selected strangers gets you into the groove of it, helps you develop some ideas about how you want to present, makes you work on your conversational skills, helps you perfect the quick and graceful exit. We should all be adroit at these things.

2. It's pretty good for your self-esteem. Sure, there are the winks ('s way of flirting) that go ignored, the men you email who don't email you back (I was sure that many of my failures had to have been the fact that I had to come clean in my profile about having four children -- that's got to be a turn-off for lots of guys, right? Or maybe some men ignored me because I'm half Black?), but cest'la vie -- the fact is, you gets tons of email, more winks than you know what to do with, and a regular stream of men you can go out with if you're so inclined. That's a confidence booster, or at least it was for me.

3. If you're open to it, you hear a lot of interesting life stories, meet people from all walks of life, and that's stimulating. No matter how many loving and fabulous friends you may have, when you're single it gets tiring going out either in gaggles of women or with your couple friends. It's nice to get some fresh blood, to see the bigger picture.

People worry they might meet freaks, or have a nightmare experience. All I can say to that is that I didn't have a single one. The absolute worst encounter I had was with a manager of a five star New York hotel, who, half-way though our glasses of Pinot Noir, leaned over to ram his tongue down my throat. Ewww! But big deal, I just got up and left. And there were the funny dates, like the guy whose profile said he was an actor, but who confessed over sake that he was a professional clown for children's birthday parties. I just couldn't see myself dating Bozo, but he was super nice. There was a former alcoholic manic depressive drummer I found sexy for a couple of months, but then realized he had rage issues. A motorcycle-riding lawyer I just didn't click with. An opera singer into S & M. The list goes on, and it was often trying, but also funny, and great fodder for girlfriend conversations. Also, as I said, a great way to learn about what I did and didn't want.

At one point when I was crying to my therapist about the latest insult or failed mini-relationship, she said to me "dating is hard until it's not." Banal perhaps, but later I realized truer words could not have been spoken. You date and date, and get hurt, and hurt someone, and have bad sex, good sex, no sex, and then boom! one week you're on a third and then a fourth and then a fifth date with someone who seems to be kind and sane and sexy and maybe all the things you've been looking for.

That's what happened to me. I'd broken up with one of the set-ups and was feeling discouraged, not sure I could face again. I took a vacation alone to Miami and there on the beach read a self help book called "Meeting Your Half Orange" by Amy Spencer. Ms. Spencer's thesis, not totally original, but exactly what I was ready to digest, is that you can't meet the right person until you know exactly what you want and you believe that you deserve it. Basically another look at that oldie but goodie: "no one can love you til you love yourself."

I started to really think about that, not just my own list of must-haves -- a big reader, emotionally engaged, not a pothead, an interesting career, someone who would sleep in a treehouse with me if asked -- but how would the right person make me feel, how would we feel together? Imagine that, visualize it, and then believe that it will come, that you deserve it.

I met the man I now love, Joe, on, two weeks after I got back from Miami. Our first date was pleasant, but lackluster, in a local bar in my Brooklyn neighborhood. I remember thinking, "This guy's okay, smart and easy to talk to, but if he walks me home and sticks his tongue down my throat I will just die." Joe must have picked on my vibe, because he walked me about two blocks, gave me a chaste peck on the cheek, and took leave for his car. He didn't even walk me home! Not sure what to make of that, I didn't give him much thought that night, or even the next day, til he emailed suggesting we go out again. Two dates later we had our first real kiss sitting inside a Richard Serra torqued ellipse at DIA Beacon. That was over a year ago.

So give it a try, be adventurous, get out there!