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Mistress of the Mix: Letter To My Former Flirtation

About a decade ago, I thought I was ready to learn how to date the opposite sex. I was newly single after a pretty miserable marriage between two mismatched people. The only thing we really had in common anymore was our love for our daughter, and that really shouldn’t have been enough to keep us together. But we kept plodding along at it, and by the time we finally went our separate ways, we had been together for 18 years. And I’m not proud of that fact. Because we should’ve given up long before then.

I bring it up because I want you to understand how inexperienced I was at dating. As a teenager, I almost never dated, because every first date turned into a long relationship. I met a guy when I was 15 that I dated until I was in my first year of college. At 18 I met a man that I was with until I turned 21. At 22, I met the man I married.

So there I was, freshly single, and 41 years old, finally ready to date. I wasn’t really looking for another husband, I just wanted to have fun. I’m a fun girl, right? So I thought it was going to be relatively easy.

I was so naïve. But then again, I hadn’t had a first date since 1989. Everything had changed since then. I just didn’t realize how much. As it turned out, dating after 40 turned out to be one of the most ridiculously frustrating experiences of my adult life. Especially because I tried that newfangled dating trend that hadn’t been around the last time I was in the game. Internet dating. It’s not for the faint of heart, especially for those of us who remember a time before there was a thing called the internet.

I actually paid good money to an online dating site in the Spring of 2008 to get my profile out there on the world wide web for three whole months in hopes of getting connected with potential dates. In my profile, I described myself as a voluptuous fireball, a music lover and expert Boggle player who was looking for a man with a wicked sense of humor who wasn’t intimidated by confidence.  What I ended up with were a bunch of hilarious and semi-humiliating stories, my dating pratfalls. I racked up so many pathetically funny stories of my lame dating encounters that I started detailing them in a blog, Kiss And Tell The World.

I’ve locked that blog down now, but every once in awhile – usually when one of my girlfriends over the age of 40 finds herself back out on the dating circuit – I’ll open it back up to share with her just so she’ll be a little bit more prepared for the surprises ahead. Surprises like the time I realized the fella I’d been on a few dates with wasn’t a divorced father of two, he was the very married father of two kids who were out of town for a few weeks with their mom.

It only took a few months for me to decide to shut down my online dating profile, and I’ll tell you why. It was when I realized that a pattern was emerging. It was a pattern so obvious that I even tested it in a sort-of scientific experiment of sorts. Not just once, but twice. And after the second time, I cancelled my account and vowed to never ever do the one thing ever again that guaranteed I wouldn’t get a second date, and most likely meant I wouldn’t even achieve the goal of a first date.

That thing? That one thing, the common denominator that was putting a hex on all my potential first dates? Instead of just telling you, I’ll share with you a letter I wrote to my last potential first date. A man that I had been carrying on a pretty decent internet flirtation with for several weeks, until I did the thing. That thing I had already tested and proven that I shouldn’t have done if I wanted a date.

Dear Former Flirtation from Fairfield,

I know we had a date set for tonight, and I know you’re not going to show. You haven’t told me, I just know these things. But before I set my backup plan in motion and settle in for a Battlestar Galactica marathon, I wanted to share with you the story of my phone number jinx. Maybe I should call it a curse. You see, every time I give my phone number to a man, it pretty much guarantees that he will fall off the face of the earth.

I know, sounds stupid. But hear me out. It’s actually sort of a fascinating sad tale of my recent dating disasters. I was gonna wait to tell you. But, well, you’ll see why I’m telling you now.

Months ago, I had a date with a guy. It went well. Really well, I thought. At the end of the evening he asked me what I wanted. He wasn’t really clear what he was talking about, but I said, “I want you to call me.” He said he definitely would. So I gave him my phone number. 

He most definitely never did.

Oh well. Moving on.

The next man I gave my number to was the first person I ‘met’ online. Local guy. We talked back and forth for a few days, he wanted to meet me right away. So I gave him my phone number. Never heard from him again. I even wrote to him about a week later wondering what happened to him, because he seemed so eager. He didn’t even bother responding with a polite rejection.

I was perplexed, I had questions unanswered. But I kept moving on.

The 3rd man was a nurse who worked at a children’s hospital in Sacramento. We had been corresponding for a while, when we finally decided we wanted to meet. We had a great connection. He wanted to drive up here, so we made a date. For the following Sunday.

So I gave him my phone number so we could at least speak to each other before the date. That very night he went out with some co-workers. The story he gave me was that he started gushing about me and our connection to one of his friends. One of his female friends. By the end of the night, he was smitten with her, and decided to break off our date and all communication so he could focus on her.

Moving right along.

It was then that I became convinced that I had some kind of phone number hex. So I did an experiment. I accepted a date with a guy who had been hounding me for a date while I was interested in the nurse. I had politely declined (telling him the truth, that I had a connection with someone else at the moment, but thanks). But truthfully, I had absolutely no interest in the other man whether or not I had a connection with someone else. To test the hex, I emailed the man and told him I’d have dinner with him the next evening if he was free. He was. I told him to meet me in front of the Cascade Theatre, and just in case, gave him my phone number. Then I just sat back and waited to see how long it would take him to break the date, or prove my theory wrong.

Twelve hours. 

Twelve hours later, I had an email breaking off our date due to a family emergency. I was pretty relieved this time, because I honestly didn’t want to meet this guy. I was just proving my theory.

From then, I have made a steadfast rule of not giving my number to men that I’m interested in. Except for you. So I take full responsibility for whatever it is that caused you to drop off the face of the earth.

So I apologize for giving you my phone number. Because I really enjoyed talking with you and was looking forward to meeting you. I was pretty convinced that we would really like each other in person and that we’d have a great time together. I looked forward to receiving your emails, which were so funny and smart, and I was having a really good time writing to you. It was just a dumb, weak moment when I convinced myself that the whole phone number jinx wasn’t real, but I now recognize, respect and surrender to the power of the curse that has made it virtually impossible for me to successfully get a date. 

So don’t feel bad that you went into radio silence right before our date. It’s really not your fault, no matter what happened.

I never sent that letter, but I also never heard from the Former Flirtation from Fairfield ever again.

If you’re wondering if there’s a happy ending to this story, there actually is, and if memory serves, it happened about a week later. That was when my parents told me that my former junior high school boyfriend had looked their number up in the phone book, and had called looking for me. My mother (who must have known all about the jinx), refused to give him my number. Instead, she told him that she’d be happy to give his number to me, and that I could call if I was so inclined.

I waited about a week, and then I called him (from my work phone), and it took him all of five minutes to ask me if he could drive down from Oregon to visit me that weekend. I told him to meet me Saturday at 5 in front of the Cascade Theatre.But I didn’t give him my phone number. Because, you know, the jinx.So yeah, of course he showed up. And of course I married him.

Perhaps you’ve got tales of dating pratfalls of your own to share. In fact I don’t think I’ve met a person over 40 that’s re-entered the dating scene that doesn’t have a story or two (or twelve). So go ahead, here’s your safe space. Let it all out. And while you’re at it, check out the streaming playlist below, the Internet Dating Lament. It’s not easy to find good songs about internet dating. But it’s really easy to find absolutely horrible, awful songs about internet dating. So I’ve collected a whole bunch of them just for you (aren’t I sweet?) and they’re all right here. But today’s playlist comes with a bonus. I’ve found that besides really bad music, internet dating has also spawned some pretty funny comedy routines on the subject, and you’ll find some of those intertwined with the music. Now that I think about it, mixing in comedy makes for a perfect playlist on this subject matter, because that’s pretty much what I was left with after my foray into internet dating…a couple of funny stories.