20 Years of Dating… and I’m Still Going.

Allow myself to introduce… myself: I’m Ashley. Shameless “Austin Powers: International Man of Mystery” quote stealer. California native. Mid-thirties singleton. Serial dater.

That last one is what we’re going to be talking about today. And going forward. As Rhi put it when she gave me this opportunity to write for MM “you pick your beat and write what you feel is the right fit. I figure career/dating will be great.” Why, may you ask did she feel the dating beat would work for me? Because I’ve been doing it for the better part of the last two decades.

Yep. 20 years. Of dating. 20. Years.

Fuck. How did I get here?

I’m officially a “Sex and the City” quote come to life. Who can forget when Charlotte—the eternally optimistic, always hoping for Prince Charming, innocent-yet-not-so-innocent Upper East side character we all secretly aspired to be—dropped this bomb at brunch with the girls: “I’ve been dating for 20 years. I’m exhausted. Where the hell is he?!”

It’s a great question, and frankly, one I do not have the answer to. This isn’t going to be a maudlin recollection of sad stories of heartache and heartbreak. Don’t worry.

My goal with sharing my stories here in this space is to make you laugh and invite you to commiserate with me.

For those of you who aren’t single, it’s a reminder that the grass might not always be greener. And for fuck’s sake, stop saying things to your single friends like “I don’t know if I could survive dating right now,” because trust us.


I’m sharing these funny, ridiculous, bat-shit-crazy, sometimes odd, and just plain random collection of stories from the last 20-years of my dating life, so you get to see, that while there’s plenty of happy and sad, there’s a lot of crazy in between.

I guess the hope is to prove, while we might all aspire to be in a relationship, there are plenty of people out there reminding us—on a consistent basis—we’re enough on our own.

My romantic education has come from a multitude of sources: movies, books, weddings, my relationships (friendly and romantic), my friends’ relationships, as well as my parent’s relationship, and traumatic divorce. It also comes from places like Tinder, Bumble, Match, eHarmony, Facebook, the local bar, workplaces, and a host of other spots.

I’ve spent a lot of time believing I was in love, out of love, angry, depressed, and feeling alone. I’ve laughed my ass off. I’ve been lucky to watch my friends fall in love and get married. I’ve watched some of them fall out of love and unfortunately, get divorced. I watched my family shatter in an ugly way, and can look back and see how it utterly diverted the course my life was on. Not a bad thing, just something that’s happened to shape who I’ve become.

As an author’s note, I overuse the word “fuck,” and frankly, I swear too much in general. Rhi loves that about me, so I’m giving you fair warning, she won’t rein that in. Also, some of these stories take a turn for the racy. Prepare yourself.

One of my favorite quotes is from the movie Auntie Mame[1]: “Life is a banquet, and most poor suckers are starving to death!” Think of my stories as the pupu platter of my dating life, over the last 20 years.

I hope you enjoy. And make sure you have some Tums for after.

And now, here’s a taste to whet your palate.

Kevin: The Tinder Experience

So I joined Tinder. 35 years old, and yup, I joined Tinder. There’s gotta be something wrong with this, right?

As I told my best friend, “I feel like an anthropologist. I completely get that Tinder is where you go to find someone to bang. I’m like Jane Goodall, studying 30-something singles in greater Orange County in their natural habitat.”

But seriously, what the FUCK is wrong with people on Tinder?

The shift from actual dating mores, like what I cut my teeth on in the mid-to-late 90s, happened I’d say somewhere around 2010-ish (very scientific research and facts I’ve got here. Deal with it.) That’s when online dating started to explode. Suddenly, girls started going home with guys who bought them a single beer and giving it up no problem.

In my opinion, that’s when the shit really hit the fan. Now, there’s not even an opportunity to get a goddamn drink. Guys just want you to bang them. And send them pictures of yourself naked. Literally, they unabashedly expect you to text them photos of your hoo-hah in all its glory.

(Insert repulsed shudder here)

Thanks, guys, but this lady’s got standards.[2]

That’s what brings me to Tinder. And to Kevin.

Kevin’s profile states he’s 37. Kevin has very attractive pictures where his muscular arms are shown off, or his bright green eyes pop. Kevin is not looking for his soul mate. Kevin is looking to have some fun. Kevin is not going to lie; he’s a very sexual, passionate person.

Translation: Kevin thinks he’s hot shit and is looking to bang the next available, willing vagina.

Good news for me. Kevin swiped right on me. We matched up.

Joy! Bliss! I’m plotzing.

So we exchange some banalities via Tinder’s chat interface. This is gold right here guys:

Kevin: “Hey, what’s up?”
Ashley: “Hi! Not much, it’s a Monday so I’m just hanging out. How are you?”

K: I’m good. Give me your phone number.

A: Why do you already want my phone number?

K: Do you have a iPhone? [3]

A: Why do you want to know if I have an iPhone or not?

K: Wanna FaceTime and mess around?

A: When you say “FaceTime and mess around” do you mean like you’re going to call me up, whip out your dick, I grab my vibrator, and we have phone sex?

K: Yeah. You down?
A: Um, no, thanks. I’m good.

K: Whatever, drama.

A: Yep, that’s me. Drama central.

K: Bye.

And thus went Kevin by the wayside. We hardly knew ye.

I imagine you’re readily judging me for swiping right on someone who so clearly was looking just to bang.

But folks, I didn’t join Tinder thinking I was going to find the love of my life. Granted, I didn’t join it to turn my bedroom into a revolving door of different dudes nightly.

I joined it to see what the fuss was about.

And I get it. I so, so, so get it.

Tinder is where morals go to die.

It’s where dudes, like the dear, sweet Kevin, go to troll the girls in the world who are willing to do ANYTHING to be with a guy that seems to be attractive and desirable.

When in reality, he’s a poor excuse for a man.

I think my favorite part of the whole exchange, aside from being able to share it on social media with my friends, was the fact that he called me drama.

Poor Kevin, he has no idea.

Ladies, I wish I could say Kevin was the worst Tinder had to offer, but really, I’m just getting warmed up…

[1]  If you haven’t seen this movie, go see it now. It’s on Netflix, rent it, buy it whatever. It’s fucking hilarious.

[2] My friends may say that’s debatable. But I like to think I have them. I might not always apply them, but I have them.

[3] I feel the need to note here that Kevin’s use of “a iPhone” was the beginning of his downfall. He could have told me he was Tom Brady and was in love with me and there are good odds things wouldn’t have continued.

6 thoughts on “20 Years of Dating… and I’m Still Going.

  1. Great stuff, Ashley. I love your writing, if not the subject matter. 🙂 Remember the pre-iPhone/Facebook era, when we huddled around desktops and logged in to sites like HotorNot and Friendster? Totally get where you’re coming from about the perversion of online dating. It was so much simpler in the early ’00s.

    Liked by 1 person

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