My First Match.com Date

(As you might guess I’ve been terrorizing the online dating world for some time, but I wrote this one a couple years ago after my first date.)

A conversation: 

Him: “Dude, I’m telling you…Match.com and Yahoo Personals is where it’s at.”

Me:   “What? Explain.”

Him: “Dude, no joke, I’ve fucked at least thirty girls from these sites.”

Me: “Bullshit. Really? I mean, I’ve heard stories about this online shit, but nothing like that. Wow!”

Him: “Yep–two or three dates maximum, and you’ll be hittin’ it.”

Like any man with social skills, I had grown up thinking that any guy who had to resort to the Internet to find a date was either a suicidal schizoid or an ex Magic: The Gathering card game champion. And I had convinced myself that no hot girl would ever go to the Internet to find a man. I was wrong. The online dating revolution had started years ago, and I was missing the ride. So, I hopped aboard with the rest of the dating geeks and pierced the wacky realm of online dating.

It started off slowly. I entered the website thinking I was God’s gift to cyberspace. Expecting an overwhelming response, I sent out hundreds of winks to any girl in Orange County who was an eight or above. Only two girls returned my wink: both were girls I almost didn’t wink at. To my dismay, only about twenty percent of the winked-at girls even looked at my profile (There is a sleazy feature that allows you to see who looks at your profile.).

I specifically only went for girls aged twenty-seven to forty-five. Any girl younger than that was considered “Plan B.” I cut off the young girls for two reasons:

            1) They’d probably want a relationship, with feelings.

            2)  It would take at least four dates to fuck them, and they’d want feelings.

Nothing wrong with feelings; I’d just rather use my feelings on a woman who actually understands her own. Even though I’m no stunning intellect, I refuse to tolerate most younger women because of their consistently unattractive traits: self-absorption, disrespect, carelessness, dishonesty, inexperience, naiveté, and materialism. That, and I don’t have the patience to go on a myriad of substance-less dates with a dopey hot chick just to finally attain a few minutes of sexual gratification in exchange for hours upon hours of hearing “Yes/No/Really?” answers and “I know, right?” confirmations and contrived attempts at sincerity. Anyone who does is working too hard for pussy. 
 
At least with most older women, there is no bullshit. They understand what men want, and they give it to them if there’s something in it for them. No games. Less rules. More sex. As long as you are honest and don’t make them out to be a whore, stimulating sexual relationships blossom. This is the beauty of experience and age. Young girls are unable to understand that sex can be fun and meaningless at the same time. If I were to discuss this notion with them, they’d throw a hissy fit, call me an asshole, and say, “Well, I hope you find yourself a nice whore! Goodbye.” Then they’d storm off or slam the proverbial door. Fuck that.

Either way, my winks weren’t working. I adjusted. I only displayed my seven sexiest photos, which ranged from me wearing bathing suits to business suits to club attire in order to portray my pictorial charisma. I changed my cocky profile to something more romantic, writing less about myself and more about “qualities of cool women,” which included girls who “smile,” “laugh for real,” “take risks,” “can handle sleeping bags,” “take adventures,” “care about loved ones,” and “cut losers,” among others. It was amazing how many girls would message me claiming they “have those traits.” I provided more information about my “hot spots,” which did not include Starbucks, and I changed my username from the trendy “OCguy37653422” to something more daring like “adventureguy789.” I ditched the winks and started sending teasing messages about one unique thing about their profile description or pictures. Suddenly, the messages began to pour in.

I heard from a twenty-three-year-old blonde fitness instructor: “Math teacher, huh. I was never any good at math, but I made it through. Just wanted to say hi. Write back!”

“Soooooooo I loved everything you wrote in your profile, but what’s wrong with bustiers?” was from a thirty-one-year-old Hispanic veterinarian.

“Hey there. Got any crazy plans this weekend?” wrote a streaky-haired hairdresser with one too many photos of her cats.

I did get bombarded with a few emails from girls with faces in the shape of a basketball, but there was one girl who distinctly stood out from the riffraff: Wendy, a sexy forty-year-old “searching for a man 26-42.” Her page displayed professional modeling photos of her in seductive positions on chairs, in white rooms, on a king-sized bed, and she was actually smiling in her pictures. After a few short messages back and forth, we agreed to hang out on a Sunday night at a local pool hall–her idea. I really didn’t care. As long as she wasn’t one of those coffee-date girls, I was happy. Just because that coffee place in the sitcom “Friends” looked happy and lighthearted didn’t mean coffeehouses were actually like that. Apparently delusions are acceptable to some girls. (Update: I’ve changed my mind about coffee houses. I’ve been on too many bad dinner dates lately and no longer feel like paying fifty bucks on a dead-end chick when I can be spending $2.50 on a tall frapaccino and ditching her in twenty minutes.)  

I was scared. I had heard the horror stories–hot in her pics, disgusting in person. This would officially be my first online girl ever. And I know myself–I’m not the type to run away; if she turned out to be repulsive, I would have lived with my misfortune and stuck it out for an hour. Sadly, when it comes to non-sexual affairs, I am a follower of the “treat others as you’d want them to treat you” rule. I have my parents to thank for that.

I entered the pool hall and the first thing I noticed about Wendy was her height. Since she had modeling pictures in her profile, I assumed she was probably at least five ten because every model in professional spreads mysteriously appears close to six feet. But when I saw a five-foot-two-inch blonde woman–with heels–in a sundress waving at me from across the bar, I was a bit surprised. Nothing wrong with a short girl, but it’s just strange how my mind skewed her appearance. Nevertheless, she looked just like her pictures: sexy.  

Wendy destroyed me at pool. After a third consecutive thrashing (I tried really hard to beat her after the second loss, but her pool skills were well-refined), we sat down at a table and talked. Even though we were having a stimulating conversation, suddenly I felt strange, as my subconscious reminded me: “Dave, you found this chick on the fucking Internet. She’s probably not that cool.”

Other than that, everything was going well. The conversation sparkled, the questions volleyed back and forth at a fair rate, and she cleverly threw me sexual innuendos. After one shot in which she pocketed two balls, she looked at me, smiled, and said, “I’m good at that.” But I was most impressed by her dating stories. Experience from dating online guys for months by then, she told me she got hundreds of winks and messages a week; she didn’t even read them all. If the guy wasn’t appealing in his photo, she’d skip to the next one. I was flattered when she said, “Yeah, you were hot, and, I don’t know, you seemed confident.” For a moment I felt like I had beaten out all the douchebags. Deep down, however, I knew she had probably fucked dozens of those guys.

As a goodbye, she made out with me. Mid-make-out we briefly discussed our next meeting. She taught grad school on weeknights, so we wouldn’t be able to hang out again until the following weekend.

That night, I went home and masturbated to a milf porno.

The ensuing week, we texted back and forth, making plans for that Saturday. When Saturday arrived, I was all business. There would be no beating around bushes. The situation felt like I was strategizing for a mind-wrenching game of chess. We had already made out, so if there wasn’t any progress, I would be indirectly communicating to her that I wanted something serious. The phone conversation was critical. After talking about our days and settling on a time, I made my move.

               Me: “You want me to pick you up?”

               Her: “Ummmmmm.”

               Me: “It’s no big deal. I don’t mind driving.”

               Her: “Ummmm.”

               Me: “If not, it’s cool.”

               Her: “No, it’s fine.”

               Me: “OK, what’s the address? I’ll MapQuest it.”

               Her: “Can I pick the restaurant?’

               Me: “Sure.”

She can have a bishop, but I’m taking the queen. Picking her up meant we’d end up at her place drinking beer or wine or champagne. She wouldn’t be able to resist me. Sex would surely follow.

Our dinner conversation was abominable. Apparently Wendy had an obsession with boats. She couldn’t stop talking about them: Catamarans, Dinghies, Houseboats, Motorboats, Pirogues, Sailboats, Schooners, Skiffs, Yachts, on and on and on. I tried to be an active listener, nodding my head and keeping eye contact, but my smile had faded. I ate my pasta quick and messy. I had food all over my face, but I didn’t care. Twice she motioned her hand to her face to indicate I had food on my cheek. I wiped it off impatiently. This dinner had to end.

After dinner it got worse. The restaurant was also a bar, and there was a dance floor. They were playing 80s music; she wanted to dance, but I didn’t. I used my favorite excuse, “I can’t dance to this music.” She couldn’t protest, it’s understandable, and I won’t get judged on the-way-a-guy-dances-is-an-indicator-of-how-they-are-in-bed theory, thus preserving my mystique. 

She begged incessantly. Luckily, I ran into an old flag football acquaintance I knew from college. When she asked if it was okay if she danced with him, I exclaimed,“Yeah, of course!” Anything to stop the pleading. Even if it might cost me sex, I’m not dancing to Cyndi Lauper’s “Goonies” song.  
 

I relaxed on a barstool, babysitting the last few sips of my no-longer-cold beer. After two songs, she excitedly ran up to me. “Okay,” she panted, “we can go now.” I smiled, took her hand, and we took off.

Her house had boating paraphernalia everywhere–books, paintings, models. Then came the moment of the night.

 Me: “Do you own a boat?”
 Her: “No.”

There are some things in life I will never understand. This girl was one of them. She had a huge house and six-figure salary, yet wouldn’t indulge in her one true passion. That’s like being obsessed with porn but never jerking off.

             I forgot about her contradictions when she brought us two glasses of champagne, and we made out on the couch.
             I took her top off, exposing her fake breasts, of course.
             I sucked on them.
             We made out more.
             I suggested we go to her room.
             She said, “Do you really want to? I don’t do one-night-stands.”
             “Me neither,” I lied.
             “If you sleep with me once, you have to come back a second time.”
             “Duh,” I lied.
             We went to her room.
             Then we fucked.

              Checkmate.

As we lay in each other’s arms, she admitted that she “knew” I wanted sex. I asked her how she knew. She said, “I knew when you asked to pick me up. It was obvious. But I figured, well, that could be fun.” I love older women.

Despite her positive attitude, there would be no second go-round with this girl. While she was honest with her sexuality, the nautical dinner conversation killed her mental allure.

Engulfed in the online dating world, I am currently sifting through a daily dose of online women, lining up dates when convenient. Wendy was my first, but cyberspace is infinite. I am now officially an online predator.

 

  • That detail about her obsession w boats is like something from Salinger. Got me turning it over. Nice yarn you’ve spun here.