I’ve always been a believer that things get better with practice. I’ve done this before; I know how this goes; experience is the best teacher, etc., etc. I always told my wife Julie that I loved her *more* knowing what I knew after 20 years than I did when we first got together, or had our first fight, or first child, or whatever.

Well fuck me, but that is NOT turning out to me true this time!

“This time” is dating after loss, or “Finding Love After Widowhood” (subtitle of a great program by my friend Michelle E. Vásquez), “taking the leap,” “putting yourself out there,” “nothing ventured, nothing gained,” or whatever the heck you want to call it.

This time, it sucks.

The first time was SO different!

I hadn’t dated in over 20 years. The shock of the first few months was wearing off, but the drudgery of being a solo parent, solo homeowner… solo EVERYTHING, was wearing me down. I embraced with gusto the notion of, “How many time does life give us a second chance—a “reset button”? I jumped into the idea of dating, not expecting to find the next love of my life, but for company, interaction, connection and possibly intimacy, knowing I had a lot to offer and had learned a lot about myself and relationships since I was last “looking.”

Online dating made it easier still. First, I could be upfront and transparent about my situation, my widowerhood. Everyone who would run screaming can and did, only I’d never have to know about it. No awkward conversations in loud bars (like Hyla’s) for me! I’d let them screen themselves out—pure genius! (Or so I thought.)

Then there was the shopping experience. See, I work in creating terrific online experiences. Helping you find the product or service that’s right for you, in the way that is most natural, logical, comfortable for you. (Or at least for most of the “yous” who make up the target audience for the product or service.) I have always been drawn to interactive because it puts the customer so much more in the driver’s seat. Social media and user-contributed content (reviews, etc.)—same thing. It’s empowering.

So, transposed into the world of online dating, I got to go “shoppin’ for love,” just like the Jane, his wife song Julie was performing when I was falling in love with her. It was great! “Oooh, she looks nice. Let’s see… ‘doesn’t want kids’? Oh, well. Next!” I got to feel superior, knowing I had in fact managed to fulfill the “till death do you part thing.” Knowing my tall wife didn’t rule out guys who were shorter than her, I got to disdainfully dismiss all those “tall” women (“You call that tall? I’ll show you tall!”) who only wanted guys 6’ and up. Rule ’em out, rule ’em in, I collected a long list of “favorites” for future consideration. Then, when I felt like pulling the trigger, I’d dash off emails to the “best of the best.” Or, when someone really blew my socks off, I’d stop everything and write them on the spot.

Sure, it took a little bit of the wind out of my sails when I only got a response from one out of a dozen emails I sent out. Or when I got the ones that said, “I really feel for what you’ve been through, but we are not a match.” (They were so definite sometimes, I started to wonder if the concept had been taken over by the Brand, as in, “I’m sorry, but we’re not a Match™.” Was there some documented criteria I hadn’t heard about?) But that was still OK. “Hey, I’m putting my real self out there, and I only want someone who thinks that’s awesome.” I posted about it here, and got lots of support. “Good for you.” “You’re so brave.” And so on. Anyone who thought it was “too soon,” or somehow disrespecting my life with Julie kept it to themselves, which was fine with me. (And still is, BTW! So STFU!)

I went on actual dates. I talked, I listened. I wasn’t a complete social incompetent, like I was in high school. I corresponded, I emailed, texted. I didn’t have (not till later, anyway) anything like what I would consider a “bad” date. I’ll save you all the blow-by-blow (sufficiently documented elsewhere), but suffice to say that when love knocked my socks off, big time, I was ready. Surprised, grateful, but ready.

I enjoyed the journey. Widowhood teaches people many things. One of the biggest for me has been that destinations are largely illusions—all we can really count on is right here, right now; the journey. As someone who has always looked relentlessly ahead, to the next good (or bad) thing that might or could happen, this was huge. The person I was sharing this journey with was very encouraging of this, of us enjoying what we had, without worrying too much about blending families or other things that were way down the road. Right now was really good, and there was no reason not to be fully present in it.

Then there was the sex. While keeping things PG-13 and respecting everyone’s privacy, I have to say, I was not prepared for how great it could be. Kids and cancer have a way of sapping the sparks out of a marriage, and it had been so long since I had participated in a really great experience that I was quite blown away by not only the experience itself but also the positive feedback. “Really? You think I’m *good* at this? Well, I’ll be!”

So, just as quickly as it went up, down came my profile. No more shopping for me!

It was so wonderful to talk, just talk. Almost every night on the phone. About life’s ups, downs and sideways; about us, our feelings, anything. A caring adult, with whom I could share just about anything, to laugh, cry, commiserate with.

When the kids and I went on vacation, communication was of course less frequent, but the tone and nature of everything seemed the same. For the first time, I talked to the kids about how I had someone I could call my “girlfriend.” Having heard me caution and warn them about the ups and downs of grown up men and women, they didn’t seem too shocked. In fact, they tried to sound all savvy and in on the scoop—“We’ve known THAT for a long time, DAD!”

But then, even more quickly than it began, poof. Gone. Over. Back to just me and the grind.

It’s funny (not funny ha ha, of course)… I transfer my malaise into so many different mental/emotional rat-holes. The election got really got me worried, and so in the month after our return home I spent more time than usual on Blue Oregon and Twitter, countering Republican spin with one hand and Democratic despondency with the other. I spent who knows how long superimposing red vs. blue by county maps from different elections to find a more liberal but also more rural place to move to… Should I change careers and become a high-school teacher in a mythical liberal small town somewhere? Maybe I should check out Americorps… or agonizing why different people act one way or another… gee, my traveling writer friend’s pictures from Scotland are so gorgeous, I wish we were there, now… Meanwhile, at any given time, the kids and I could be hungry, they needed different things for school or Halloween or whatever, and all I wanted to do is go back to bed. At one point I seriously felt sick to my stomach for a solid week. Blech, blech, blech.

I also couldn’t write. This post got its start during that period. I started and abandoned several Facebook notes about being broken up with but finished none of them. I got some nice support from my friends when I posted a cryptic note about being thrown under a bus, but I didn’t really feel like I wanted a whole lot of attention over it, so when it faded, I let it.

Slowly, I dipped my toes back in the waters of online dating. But my original enthusiasm and gusto were only a vague memory, something my recent relationship was quickly becoming, too.

It used to be, I’d browse the profiles on match.com, reveling in the world of possibilities. I joked about being an Internet Dating Slut—so many wonderful ladies, so little time! Now, scrolling through my list of “Favorites,” I’d be depressed by the “might-have-beens,” the profiles who’d disappeared because they’re “no longer available.” (“Wait, who was that? Not her! I liked her!”) Or I’d re-read the profiles I’d thought were promising only to discover reasons not to bother. Words and phrases like “ambitious,” “love my career,” “knows what he wants,” “I never slow down for long.” I felt like I didn’t know any more what things like that even meant. Ambitious? For what? Money, power, fame, “success?” Career? My life has been completely turned upside down—I have no idea what the fuck I want to do, or what I would consider “success.” Some days, getting dressed counts as success. I enjoy the city but love the peace of the country. I might want to move; to Washington State, Massachusetts or Vermont, or the UK if they’ll have me. (They won’t.)  Some weekends, all I want to do is sleep—is that so terrible? Apparently so in the online dating universe.

Also, I’m “old.” I’ve been told that women, no matter their age, will routinely attract interest from men 5, 10, 15 or more years older. That must be why almost every profile I look at sounds like an ad for “Cougar Town”: 42 year-old woman, seeking men 30 – 45. 38 year-old woman, seeking men 32 – 39… WTF? I gather Stella wants her groove back. Well, I’ll have you all know that my 49 year-old “Stella” found this only 3 month younger fellow quite sufficient for groove restoration, thank you very much! Unfortunately, having completed my “mission,” I was apparently no longer needed. More blech.

Maybe match.com needs testimonials or recommendations, like Amazon or LinkedIn: “I slept with Jay for 3 months. Wow! I had more orgasms in that time than I’d had since my thirties! Five stars!” Too bad my best long-term reference isn’t talking a whole lot these days.

Then there are the people I’ve seen on match that I also know “in real life.” (I actually despise that phrase.) One was an online-only acquaintance, who agreed to meet for coffee after I saw her profile and emailed her about it. Despite having what I thought was a great time, she informed me afterwards that she didn’t see us being romantic because something “would really have to blow her away” to be worth bothering with. Oh, really. Nice. Someone else, who I worked with for a number of years, has yet to reply to my initial “Hey, I saw you on match!” email. Embarrassed? Terrified I’ll ask her out? Afraid of catching widower-cuties? Who knows!

Then there’s the widow I know from one of my kids’ schools, who came up to me and told me she was a widow and was so nice and promised we’d have coffee some time. Months later (still no coffee), I saw her on match. I emailed her, very low key, “Ha, ha, look at us,” that sort of thing. Still no response on the coffee, and nothing more than a quick wave at pick-up time. Then, I realize she’s disappeared from my “Favorites” list. “Ah well,” I think, “maybe she’s found someone. Good for her.” Except soon after, she pops up in my search results, only when I click on her, match tells me, “This profile is no longer available.” My fellow Jedi’s, there’s only one explanation for that kind of communications disruption—I’d been blocked! Geez. Does this mean coffee’s off?

Since I’ve started this post, I’ve moved forward; if barely. I’ve gone on two first dates, both with very nice widows. One is now looking to try things one-more-time with her ex—more power to her. The other has been enthusiastic and distant by turns. Is that what people mean when they say they “don’t want drama”? Because, whenever I see that, I think, “Oh, sure. You want a freaking fairy tale. No bumps, no problems.” Me? I want someone in the reality-based universe. Who doesn’t drop off the planet without some kind of notice. Hopefully she’s surface at some point, but still—would it kill ya’ to reply to an email in, I don’t know, less than a week or so?

Oh, and then there was the time where I was honest, blunt, but also vulnerable with an old, single friend of mine whom I’ve always thought I had a, well, “special” relationship. (No boundaries were ever crossed, but we certainly knew they were there.) We ran into each other getting lunch, and I kind of let her have it for disappearing after she promised she wouldn’t. Feeling guilty, I wrote her and apologized for being too hard on her and explained I just liked her and missed her. Three Four weeks later, she hasn’t written back.

In the online dating realm, interesting people pop-up from time to time from Yakima, or Seattle, or Vancouver B.C. So, how’s that supposed to work? Months of increasingly intimate emails culminating with a romantic rendezvous? Sorry, but there’s a wonderful online love story about that. And it doesn’t end happily ever after. (Highly recommended, though! And I have a crush on the writer—along with 90% of the Portland creative/geek/social web crowd. Nevermind.)

Wow. That lady in the grocery store sure is cute! Her husband/partner/whatever looks like an idiot. I suppose when she figures that out in ten years or so she’ll post a profile on match.com: 49 year old female seeks 30 – 48 year old male. Only I’ll be 59.

Ick, ick, a thousand times ICK!

“Positive.” “Glass-half full.” “Generally a happy person.” “Life is good!”

Lady, my glass has been shattered into a million pieces. I’m currently trying to put it back together, in hopes that it will hold water. Could you please pass the super glue?

(True story—I put something like that as my “headline” on match. Immediately, the number of new people who visited my profile? Stopped. Zip. Zero. Zilch. Nada. I’m really not sure I’m cut out for this. But at this point, I’m still convinced the alternative is worse. We’ll see. Read it here first.)

2 Responses to “It was a heck of a lot easier the FIRST time!”

  1. Cynthia says:

    Hi Jay —

    This one got a couple of chuckles outta me. Dating really does suck no matter what your age or status. I have never been married – not even close, so I can’t say that I’m “rusty” as much as merely resigned to reality or content to remain alone until I meet someone who’s right in an organic way. Maybe a fellow non-cook getting takeout from Whole Foods. Our eyes meet over the grits with smoky cheese. It’ll be something PG-rated that we can tell our kids about. Oh wait: my eggs are almost all dried up. Scratch the kids part.

    Anyway, I am sorry that the 5* orgasm woman gave you the boot after a few months. Why would she do such a foolish thing? You didn’t say.

    Hang in there and keep finding the humor in dates from hell. It’s the only way to survive. :-)

    ~ Cynthia

  2. Jay says:

    LOL, Cynthia! Thank you. I’ll PM you more about Ms. 5-star (SO needed a nickname for her, so thank you!), but bottom line is I think she got her groove back and upon realizing this decided I had outlived my usefulness. (That’s a bit meaner and more simplistic than the reality, but I’m sure you get the idea…) Part of it, though also relates to some of the other things we’ve been talking about–one of the things she said was that she had thought that a lot of the grief stuff would have “sorted itself out” by now. (This was in late September.) So, there you have it! Dodged a bullet, frankly.

    As far as eggs are concerned, there are ways around that, should Mr. Whole Foods Takeout happen to cross your path! 😉

    Take care,


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