Online Dating: To Fish, or Not to Fish?

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Online dating. It's Pole #2. Can I afford to abandon it? Can I afford not to?
Online dating. It’s Pole #2. Can I afford to abandon it? Can I afford not to?

My three-month online dating subscription will auto-renew on August 14 if I don’t cancel it first.

That’s my wedding anniversary.

I have severely mixed emotions about the entire process. And I’m not sure whether I want to invest any more time and money in it.

It’s horribly unnatural, I’m not very good at it and it tends to make me feel more bad than good.

On the flipside, I have made a few legitimately positive human connections by doing it.

Perhaps more importantly, it’s one of the Three Poles in the Pond.

And if this Celibacy Festival of Suck is ever going to end, I need to give myself as many opportunities as possible.

Online Dating: A Three-Month Review

Number of dates: 4

Date #1 – The Widow

Her husband died six or seven years ago. She had already been in and out of a serious relationship between his death and meeting me. We had a good time. She liked me. So much so that she had to cut it off because she knew I wasn’t ready to like someone back. Probably still should have made out a little, though.

Date #2 – The Doctor

This was The Hilariously Unfunny Date. I wanted to be dead almost the entire time I was with her. Imagine someone pulls into your driveway in an exotic sports car. Gorgeous. And it can be yours! All you have to do is pass your driver’s test! So you take it for a spin. And HATE it. Under the hood, there are a couple hamsters powering a golf cart engine. The seats are uncomfortable. The radio doesn’t work. And every time you hit the brakes a little gnome jumps out of the center console, does an Atomic Elbow Drop on your penis (or vagina!) and screams: “Fuck you! You’re stupid and ugly!”

That’s exactly what that date was like.

Date #3 – G.I. Jen

I met her for lunch. We talked for a couple hours. She’s brilliant. Wise. Mature. Hilarious. Kind of a badass. A workout fiend. A boss at her job. We still talk with relative frequency. She’s in the early stages of what might be a serious relationship and I’m legitimately happy for her. She’s awesome and deserves happiness. I have thoroughly enjoyed meeting her and hope to continue our platonic relationship, because I think I still have things to learn from her. Definitely should have made out a little. I’m too old-fashioned sometimes.

Date #4 – The Lady Who Said I Looked Like Jeffrey Dean Morgan in My Photo

She came to my house. I know! How irresponsible is that!?!? I told you I make bad decisions. We had a running joke about the huge well in my basement where I kept my victims and my propensity for fabricating skin suits. I made her dinner. We drank wine. We hung out for about six hours, talking about this and that, discussing music, and having a pretty pleasant time. Even though I look NOTHING like Jeffrey Dean Morgan, I appreciate the sentiment that she considers me attractive. It feels good to be liked.

The Rest of the Field

There is another group of women I’ve met via online dating that I haven’t been out with. We may go out someday. We may never. But here they are:

The Greek

She’s interesting. Exotic looking. Dark hair. Pretty eyes. Totally Greek. I haven’t told her yet that I don’t like Greek cuisine. Might be a deal breaker. If I had to handicap the field for Girls Most Likely to End the Celibacy Streak, she would have been No. 1. But then last night, she drunk texted me at 10:30 p.m. trying to get me to come drink with her an hour’s drive away. On a work night. I volunteered tomorrow. She texted: “I want you now now now now now now now now.” Good for the ego. Good for the testosterone. Bad for everything else. I’m on the fence about The Greek.

The Complicated One with a Boyfriend

I just found out about the boyfriend two days ago. She got on an online dating site after a breakup. We had some interaction. She liked me. She gave me her private email address. But then she got back with her boyfriend, I guess. She still wants to meet me for dinner one of these nights, and she made it clear she isn’t available romantically. She doesn’t want to be dishonest with her boyfriend, so she has to decide whether to lie about how she and I met, or tell him the truth, assuming we actually go to dinner. Naturally, she’s the one with the most girlfriend potential. We have a lot of common ground. She even said so. She sent me an email a few days ago that ended with: “Sent from my iPhone while shopping with my mother.” So, now, at the end of every email, we have some new Sent from my iPhone message. It makes me happy. For example, if I was typing this on my phone, I might end this with: “Sent from my iPhone while being a stupid asshole.”

The Brutally Honest One

That’s what she calls herself. Brutally honest. I don’t know her well enough to know how true that is. It’s relatively early in the get-to-know-you process. She wants to meet, though. She’s said as much. We’ll see what transpires. As I like to say these days, half the time, I’ve got nothing but time. But that’s a lie. I should stop saying it.

The First One

Ahh. The first online dating girl. You always remember your first. One time, we had the ULTIMATE nerd date, despite never being in the same place at the same time. We called each other, and we synched the start of the movie Prometheus—she’s a big sci-fi fan—so that we could real-time text with one another about the movie. It devolved into some flirty stuff I’m too embarrassed to type here. As if I can make this story more pathetic. But wait! I can! My first online dating girl is a mother of two. And one of her children has special needs. He’s wheelchair bound. Suffers from epilepsy, autism and cerebral palsy. I remember arrogantly thinking that I was man enough to be unfazed by it. That I could be her hero. That I’m capable of that much love and unselfishness. And I might be. But she got a little psycho and I dropped her like fifth-period French.

What memories are left to be made with these women? Some? None? I don’t know.

But after writing this recap, I’ve realized I’m probably not ready to pack it in just yet.

Because I can’t make this stuff up.

Yeah, screw it. I guess I’m re-upping my membership for another three-month stretch.

Happy Anniversary, Me.


I changed my mind. I do that sometimes.

15 thoughts on “Online Dating: To Fish, or Not to Fish?”

  1. Are you kidding me? Yes you should renew it!! Hell, branch out to other dating sites. Have you tried one of those christian dating websites? The women probably outnumber the men on those. Is there a singles group at church?

    1. From one Christian to another: Do you really want ME bringing my morally abhorrent behavior into a good girl’s life? 😉

  2. not to be a downer and one of the girls even mentioned said in your writing, but you’re not ready to date, Matt. I really don’t think so, not with the intent of finding the one, anyway. You can end the whole celibacy thing a number of ways, but I wouldn’t make trying to find a new girlfriend one of them. If your 3-month membership is up already, you jumped into that pretty quickly, especially since you seem to still have a lot of anger inside. I’d just give it a bit more time, and you’ll probably feel better about the whole thing. Just my .02
    Give it a bit of time, that girl with the boyfriend will be yours by Christmas 🙂

  3. You may not be ready for a serious relationship but it wouldn’t hurt to have female friends who can eventually be “the one” , once you’re ready ?. I am sure there are lots of intellectuals there who could be meant for you.

    1. Well, that’s certainly the nicest thing I’m likely to read today. That I’m worthy of “intellectuals.” And from a doctor, no less!

      Thanks for that. Made me smile.

      1. Well, you write eloquently and all your posts are cerebral, so I think you would need someone who has depth and equally adept, lest you get bored! Hey, you’ve got to believe in yourself!

        1. You read more than one!?!?

          Was it the penis-attacking gnome that gave it intellectual credibility? 🙂

          Seriously, thank you. I am a guy with some layers. And I appreciate you reading very much. Thank you.

          1. Pleasure is mine. Well the the “penis-attacking gnome” definitely did not add a tad bit in your intellectual credibility ahahaha =)

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