Online Dating: Is True Love Just a Click Away?

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In part three of this three-part series, two reporters try their hand at Internet dating (click here to read about their blind dates and here to read about their speed dates).

Cassie is a 26-year-old news editor from Ohio looking to for someone who can laugh at himself and lives in the moment. Michael is a 23-year-old news editor from Long Island, N.Y., who wants a real, hip, intelligent and, yes, good-looking woman.

Not so many years ago, when someone mentioned that they'd met a new love interest on the "World Wide Web," friends would all react the same: "Good for you!" with their voices raising an octave with forced enthusiasm.

Back then — before toddlers had e-mail accounts and most of us still mailed in checks to pay our bills — Internet dating carried a negative stigma. Meeting people in the "cyber world" was considered creepy. Why couldn't singles just meet someone the old-fashioned way, by getting sloshed at the local bar until they a) found someone drunk enough to consider going out with them or b) were drunk enough themselves to consider going out with a stranger?

For the most part, times have changed. While some still snicker at online dating, it becomes more accepted every day and has even been responsible for many marriages.

With this in mind, two singles decided it was time to give the Internet a chance to play matchmaker.


I have to admit, of all three dating strategies explored for this package of stories, Internet dating sketched me out the most. Speed dating occurs in a public place and a blind date is with a friend of a friend. But Internet dating? Can you really decide to spend time with someone based on a flattering photo and a profile they filled out in 10 minutes?

And while I've had plenty of friends use dating services such as or, I've always been hesitant to do so myself.

I have profiles up on Friendster and MySpace, two social networking sites I've used strictly to keep up with friends from Ohio since I moved to New York City three years ago.

But when it came to seeking out an actual date on the Internet, I just wasn't into it. I always deleted messages from guys I didn't know. And even though I had friends and roommates who would go on "MySpace dates" or "Friendster dates," the idea of actually meeting up with a complete stranger scared me.

However, I agreed for this story to give it a shot. Rather than go to a site constructed only for dating, I decided to seek out a potential paramour on Friendster.

With this in mind, I logged in and saw that a guy I didn't know had "viewed" my profile. I took a scan of his page and saw "Steve" wasn't a total basketcase. He enjoys running in New York City's Central Park, as do I, and made a reference to my favorite character from my favorite movie, Margo Tenenbaum from "The Royal Tenenbaums." On a whim, I sent him a message.

Crafting the first message, however, was a tricky task … how did I come across as cool, and not desperate, despite that I was seeking social interaction over the Internet? How do I get across that this really isn't something I usually do, without sounding cliché? Most importantly, how do I propose a date?

After several drafts, I sculpted what I thought was the perfect message, and before I could second-guess myself, I sent it.

As soon as it was gone, a wave of dread came over me. I had no idea what to expect. What if he didn't write back? How long was it supposed to take? At what point did I give up all together?

Almost exactly 48 hours later, Friendster alerted me that Steve had written back — and agreed to meet that very weekend. We arranged to meet at a bar in downtown New York City's East Village on Friday night.

Now, remember how I was scared to meet strangers? With that in mind, I did what could have very easily been a date disaster — I brought along a friend.

I really didn't plan to bring Kelly, but it just so happened we had been hanging out earlier in the evening, and we were still out when I was supposed to meet Steve.

While I could have given her the boot before Steve arrived, I didn't. And I was a bit relieved she was there just in case Steve turned out to be a psychotic creep.

So with Kelly settled at a table inside the bar, I went to the designated corner to meet Steve. In his Friendster profile, he had pictures of himself with a full head of hair as well as with a shaved head, so I wasn't sure what to expect. Fortunately, he couldn't miss my mop of red curly hair that has cursed me since childhood, and he spotted me from across the street.

We exchanged an awkward half hug and giggled at how weird it was to be meeting. I then quickly fed him a line about how my friend and I had met up earlier, and Kelly was inside waiting for us.

While this could have unsettled many an unsuspecting gentleman, Steve handled the situation with ease. The three of us talked, drank and laughed for a few hours. At times, I was afraid he might think I was trying to set him up with Kelly — a fear that confirmed that my first impression of him was good, and that I might want to see him again.

Eventually we decided to move to a new spot to meet up with a friend of Kelly's, and before long, Steve and I split off. We decided it was time for a late-night snack of French fries — an admitted favorite food of mine that even more confirmed that this guy was all right.

The night ended well, and I knew I wanted to see him again — something I definitely didn't expect from an Internet date, I have to say. And two months later, we're still seeing each other …


As I’ve mentioned before in this series of articles, I’m not exactly a veteran of the dating scene.

I had a girlfriend from near the start of high school until my junior year of college who was good about taking care of many of our relationship events. I experienced the single college life for the rest of my days as the big man on campus, and I just started dating in the big city.

In all the time I’ve been single, I’ve just never thought of dating. It’s too much work. But when in New York City, do as the city folk do.

I learned two things on my Internet date. One: the word “reservation" is rather valuable to know.

Two "never talk politics on a date" is not always the best advice.

I used to find my Internet date, Katie. I basically responded to the first girl who “winked” at me. Winking is the way of starting a conversation on the Web site. Someone winks ... and the other person responds with a short “Hello, how are you?” type of thing.

Me, though, I’m on the speed track. I got a wink and went right for the kill.

“I like your profile. Seems we have a lot in common. Thanks for winking at me! Wanna get drinks sometime? A casual dinner? How does next Friday work for you? If you want to get in touch with me…”

Short, sweet and to the point. The same day I got a response. Giddy up!

Katie gave me her phone number and we set up a date. I told her to pick a place because it was her neighborhood I was going to.

I, being me, didn’t put much thought into the date.

We were supposed to meet around 8 p.m. on a Friday night. It was pouring rain all day. She text messaged me that she was running 15 minutes late. Not a problem, I replied. I also asked where we should meet so we wouldn't be walking around in the rain. That’s when it dawned on me I had no clue where we were going on a Friday night at 8:30 p.m. I didn’t think that, you know, a lot of people go out on Friday evenings.

One awkward thing about the date was seeing the person in real life as opposed to on the Internet. The Internet isn’t real. Real life is.

But, I have Internet friends. And I’ve met them in real life. For the most part, they looked like pictures I’d seen.

In your head, you’re hoping she looks better than she does in her photo, and dreading that she might look worse.

Still, we spotted each other without a problem, as I was standing outside the door to the restaurant. I guess we both sort of look like our photos. That’s good.

When we went in to be seated, that's when I learned just how important that word “reservation” is.

Me: “Table for two, please."

Host: “Do you have reservations?"


“It’s going to be about an hour-and-a-half wait.”

“All right … (awkwardly looking at each other) … thanks, but no thanks.”

It’s not like my date didn’t know another place in her neighborhood to eat. I told her to lead the way.

But it was raining out, so we didn’t want to walk far. The first restaurant we walked past, we decided to walk in.

Of course, the place specialized in seafood plates of, on average, roughly $30. Great!

When the bill came, she did offer, “Hey, can I help out at all with the bill?” but I told her it was OK, and I’d take care of it. I quickly whipped out my credit card in hopes she’d not see the amount, which was more than $100.

But in all, the date went really well. Great food, great conversation, great interaction.

And what I think made the date go well was seeing how similar we were — in terms of how we grew up, the family pressures we had to deal with … and how those shaped our political views.

Yes, we talked politics. These things tend to come up when you mention you work at FOX News.

And I must say it went smoothly.

Unfortunately, I don’t think I’ll be seeing her again. We did share a good conversation, but I just felt the physical attraction wasn’t there. To me, that’s just as important as anything else.

I mentioned in my blind date article that I’m not looking for anything serious … or so I think. But if I were to consider it, I’d have to feel she was special. I didn't get that feeling on this date.

And so it goes...