50, Single & Not Really Feeling the Mingle: Why Dying Alone Doesn't Sound So Bad

Time was, the thought of being single forever and ever was the saddest thing I could imagine. Could there be anything worse? Not being part of a couple for an extended length of time was the stuff of cold, lonely spinster nightmares.

Turns out, there is something worse, my friends. It's called dating in your fifties.

Also, dating in your late thirties and basically the majority of your forties.

Hey, I know! Some of you have absolutely ROCKED the post-divorce dating thing and are living proof that love truly is sweeter the second (or third) time around. Some of my oldest and bestest friends are happily coupled up after surviving disastrous and not so disastrous splits. They are truly happy, and I am truly happy for them.

Also, kind of envious.

Because it's a jungle out here, folks. And not a fun Lisa Frank jungle full of neon parrots and mellow tigers. No, today's dating jungle is dark and dank and overflowing with ghosting snakes, married cheetahs (lol see what I did there?), dick-pic wielding sloths and commitment-phobic dung beetles.

I was starting to wonder if it was just me and my anxiety-tinged STAY AWAY vibes I seem to give off combined with my problematic and conflagrant dumpster taste in men, but in my little private hausfrau facebook group, we share our tales from the trenches and guess what? It's not just me. It's a lot of us. It's normal, everyday women who are attractive, kind, employed, smart, funny...and so completely over the dating game.

We share our experiences in there, complete with screenshots and we collectively wonder, WHAT THE EVERLOVING F*CK. WTF is wrong with these men? And please, people, don't @ me with the #notallmen. No, that's not "no tall men", it's "not all men" because guess what? It might not be all of them but sister, it's a scary number of them.

When I was first let loose out onto the singles prairie, I did what you're supposed to do. I took some selfies, wrote a poignant yet hilarious profile and began online dating. I dated quite a bit, in the beginning. Yes, almost all of those dates are chronicled here and they are pretty funny in my biased opinion. I met lots of men. Dating? HA. It wasn't so bad! I even met a couple of them organically (lol no, not at Whole Foods) and those were also easy breezy. Girl meets guy, numbers are exchanged, texting/calling happens, then the dating begins. It was simple, really. Because THAT'S HOW DATING SHOULD BE RIGHT?

After a while, I decided to put the search for true love on hold in order to be more present for my kids. This is what worked for me, I'm not advocating it for anyone else nor am I saying that if you choose to jump headlong into the search for love that you aren't an attentive parent. It's quite possible to focus on yourself AND your kids. I just had a few more fires to put out than most and decided my energies were best spent doing that vs getting my freak on. "i can wait. the men can wait. what difference will a few years make anyway?"

Oh Jenny. Oh you sweet summer child/woman.

The difference is insane. I feel like Sleeping Beauty (okay Sleeping "Looks Good for Her Age").

I woke up and learned that not only is Prince Charming NOT so charming, chances are real good that he's deep into playing games, playing the field and playing dumb.

What's that? Don't knock it til ya try it? Honey. I did try. Let me regale you with the brief tale of Blizzard 2018...

It was a dark and stormy night. Actually it was a bright and stormy day. It was December 1st, a Saturday, and a big ol' Minnesota blizzard was descending, fast. I took Walter out for a walk and when we left the house it was unseasonably warm and the skies were clear. An hour or so later, as we rounded the corner towards home, we were both coated in wet snow.

Now, for those of you unfamiliar with midwestern blizzard mentality, it goes something like this: oh man all the weather people are saying it's gonna be a doozy. But they always say that. Let's wait and see. We'd been warned but it was really nice out, ya know?

Once it really sinks in that the meteorologists did indeed nail it, the blizzard panic sets in. Most people's blizzard panic is along the lines of "okay we need bread and milk and coffee" but for me it's always "okay I guess I need wine".

So I set out to get some wine. Blizzard Wine. Listen, I don't even really like wine all that much anymore. It gives me a headache and also, wine-drunk is THE worst kind of drunk there is, at least for me. Wine turns me into a melancholy-tinged Miss Havisham, only instead of wandering around a decaying mansion in a moldering wedding dress, I stumble through our rental home in worn pajama pants and a giant, pilly Netflix sweater.

Of course wine-drunk Jenny is also the one who decides that it's time to start dating THAT VERY SECOND. It's how I "accidentally" signed up for the Gold Membership on Tinder a couple of years ago (guess what you can absolutely cancel the next morning and they won't charge you)(fist-hand knowledge, LOL). It's also how I found myself navigating Bumble on a Saturday night in December, a box of Bota's finest rose' next to me and a snowstorm howling like a banshee outside.

I guess I chose Bumble because it's supposed to be the women-empowering-women app. Women call the shots, we get to decide if and when a conversation is initiated. Of course there are a few things that would not make sense to me even if I wasn't two goblets of wine deep, like if someone "hearts" your profile, and they also had some weird time limit after swiping left (or right my god who can keep all of this straight) which is not all that different from that horrible game where you had to get all those plastic pieces arranged before time ran out.

this is that game and I have a stomach ache just looking at it
Ugh, the Blizzard story is not as brief as I promised.

Anyhoo. Where was I? Ah yes. Snowbound and wine drunk, squinting at the screen on my phone. Super dignified as usual.

Surprise, surprise. It was a shitshow. My profile was so cringey I took a screenshot of it because even in my vino-impaired state I knew it would be the most effective deterrent available if I ever found myself attempting to mate online again. Don't you love when Drunk You looks out for Sober You? Sometimes it's cleaning the kitchen, sometimes it's screenshotting the dumbassery.

Luckily only one poor soul endured the Jenny Experience that night. I mean, it was late and there was a blizzard so it could have been so much worse. The next couple of days, though? Oh honey.

I lasted less than a week on Bumble.

It's all the same. I know, yes, believe me I KNOW. I know there are decent humans out there, even on the apps! But for the love of cheese- there's so much bleah, too. And not new, fresh, somewhat intriguing bleah...nope. It was pics of guys semi-naked in beds, in bathroom mirrors and restaurant booths. It was the ones who stated, in their profiles, that they were married and just looking for quickies (yeah, high fives for being upfront and honest but come on). It was guttural, semi-literate caveman messages followed by either a request for a pic of my boobs or, lucky me, a picture of a penis.

Because this is me, one of the first faces I saw on there was that of the couch-surfing Lothario I'd taken a chance on a few summers ago. Panic set in. oh shit, if I can see him, can he see me?? GAH. Hard pass. Like, James-Franco-in-127 hours hard pass.

I saw a guy who is one of those local NPR kind of quasi-celebrities. Of course I had swiped whichever way means "interested" and so we had a little conversation wherein I told him I'd followed him on twitter for ages. Which was followed by me deleting the ever loving shit out of my twitter profile.

The conversations were stilted and forced and goddammit, men, stop with the pretending, okay? Stop acting like you're interested in getting to know someone when all you really want to do is fuck them, please? Life would be so much easier if we all just put it out there, you know?

Maybe some of us do just want to find someone to screw. In fact, I know some of us women want precisely that kind of deal. That's literally all I've wanted out of "dates" for the past several years.

And I get that things have changed. This is how it is, according to my kids and coworkers who are single and in their twenties. Some of them will gently remind me that there are age-specific sites/apps, for geriatric hopefuls and middle-aged love seekers. I mean, isn't there a dating app for everyone now? Farmers, furries, the adult-onsie crowd? You got it.

But what about those of us who are wedged solidly in between the boomers and the millennials? And even more specifically, those of us who have zero interest in these modern day reindeer games, the ones where it's okay to just stop communicating, boom, in the middle of a text/message conversation? The ones where it's the norm for a 50 year old dude to be casting his net downwards in hopes of snagging a 20 or 30 year old woman but a 50 year old woman is lucky to get a hello from a man her own age?

Maybe it's just me. Maybe it's all of those Meg Ryan movies I absorbed in the 80's and 90's, the movies where a quirky gal who wears turtleneck sweaters and loves to read stumbles across her sweet soulmate while listening to the radio or in an AOL over-30's chat room (this is the point in the post where I for real wonder if I need to translate this shit for the youngsters).

I realize this post is dragging the menfolk a little. In my defense, I have exactly zero experience dating women so for all I know there is a female equivalent to these guys. Do women do this, too? Are there guys out there somewhere, commiserating over beers at happy hour with tales of woe about the ladies who won't respond after coming on strong or who pepper every conversation with stupid lines like "omg u are srsly so handsome i bet you dont get lonly" or "I can be at your front door in under an hour" 😱

Someone in that facebook group posted about a guy she'd encountered on Tinder. He seemed okay, except for the fact that he'd been single for 12 years. Someone commented, "I bet there's a reason he's been single that long" and that froze me.

Because I've been single that long. Yeah yeah, there have been a couple semi-serious relationships and a few not-so-serious, but I have been single since December of 2006. Like, kids who were born then are now in middle school. I have friends who have been divorced, remarried and divorced again in that time and here I sit, repulsed at the thought of submerging myself into the murky dating pool once more but also, content with 99% of my life right now.

It's that 1% that trips me up. That, and the occasional wine-infused blizzard.


  1. OMG so much to say!! Once you've given up on dating-sort of the way you seem to have-and care more about your peace and comfort, it is much easier for love to find you. When you search and try hard at it IMHO it seems impossible. Also, you have to love yourself and your life so much more than wanting to date. You have to have a great acceptance of how your life is, maybe 60-70% of the time things are positive. But having someone special would only bring your life to 75-85% better. There is no 100%. There is no perfection in this fucked up life. Having a mate isn't the end all be all of this messed up world. Does this make sense?? Also, I'm jealous of your life!! You are funny AF, you are kind, sensitive, a good friend, thoughtful, so intelligent, warm, sweet, you have a ton of good friends and unknown amount of fans. You have 4 kids who love you and you love them unconditionally. I'm so proud to know you. This blog post rocks!! In keeping this theme of kicking the dead horse; please make this part of your book which will help get you your home and security until the end. I'm happy to market the shit out of it for you. I've sold drugs and RVs and medical telemetry. You name it I can do it. You are SUCH a gifted writer, another thing I'm jealous of. Lots of love and nachas!!

  2. Jennie:
    Girlfriend, you so nailed it, “Lock, stock and barrel” (no offense to the pro or anti-gun proponents.). Not one to normally (ha, ha...great word, no longer any meaning) feel “invisible”, a neighbor (single, late 50s/early 60s) told me that at a “certain age” women become invisible (not in the cool way where you can rob banks without getting caught or prank your friends). To quote Marshall Mathers, “The truth is you don't know what is going to happen tomorrow. Life is a crazy ride, and nothing is guaranteed.” Enjoy your ride and much thanks for taking us on the journey.

  3. I could have written this myself (although not as articulately). Just turned 49, single since June 2005 apart from a few what amounted to flings here and there. Online dating was a nightmare - the few that I actually went as far as consenting to meet IRL were at best just not for me, but more often obsessed with themselves and/or their exes. I gave up on it years ago. The flings have been men I've met IRL but usually only to find out down the track that they were married or hoping to get back with their wives and waving me under her nose to make her jealous (and no, I did not find that a compliment).
    Meanwhile a man I work with who I imagine is around 60, had his wife leave him earlier this year, jumped on online dating a few months later, and is now happily dating exclusively, with the first woman he met! I tell you, there are way more single women than men, so men have their pick.
    I remember reading years ago about a thing called "hotness delusional syndrome", which is caused by mediocre or worse men finding they can pull any number of high calibre women because these otherwise high calibre women just really don't want to be alone and are settling for whatever they can find. I'll have to find the link now lol.

    1. OK, googled and found all kinds of references lol, so sharing one that also links to the book where the syndrome is first mentioned. https://www.mamamia.com.au/hotness-delusion-syndrome/

  4. Yes, this is why divorce is so unfair to women. I’m 40, have 2 early elementary age kids, and I have to do “shared residency” with my cheater exhusband (who is also a John). He is 42 and dating women aged 18 (or younger) up, while I will be lucky to find someone 55+, most of whom are losers who are also likely cheaters.

    I’d rather just have primary custody and be with my kids. What am I supposed to do during the 50% of the time I don’t have my kids? Date losers? I have a daughter! Can’t we as a society agree that divorce, age, etc is lopsided to women? Why can’t women have their own kids more of the time? Oh, right, because then men would have to pay them more and wouldn’t have much money for dating 23 year olds.

    Male chauvinism is alive and well in family court.

  5. I've been single-ish for three and a half years and come and go from online dating (also deleted tinder immediately) but what I've found is you have to be willing to wade through all the muck to make a connection or two. And you also have to be sort of ruthless which is hard for women trained to be nice. Don't like someone back you don't want to kiss. Don't message someone back if you aren't interested. Don't lose time in your day to someone you know isn't a person you want to spend time with. Spend time on the people where connecting seems possible. Yeah, some will ghost - but some won't and one here or there will rise to the top. I think it requires infinite patience and an understanding that life is complicated AF and quality people on the site probably have complicated, messy lives too.

  6. Focus on your 99% - you are blessed, and truly do not need a man to complete you. You never know what will happen in the future and if it's meant to be, it will be. I know, cliché, but also true.

  7. My ex left me when I was 51 (he's 4 years younger) for a 39 year old skank with fat ankles and a face like the north end of a camel going south. Not a looker at all (you might have guessed) but I know for a fact she can sink a litre of whiskey in one sitting so maybe that was the appeal. To give credit, she is at least intelligent in an academic way - he isn't in the slightest so I never saw the attraction - except maybe the whiskey bottle - they met in the local whore bar. Anyway, she cheated on him 3 years later so he had to jump right back into a new relationship with someone he knew from high school and frankly she's even more nuts than the first one though not a bar whore from what I can tell. But he can't be on his own you see! I had a few flings after he left and started seeing a colleague I had known for 25 years but now we're just friends and I'm happy with that. The thought of living with someone again turns my stomach. As for remarrying - NEVER IN A MILLION YEARS! Why would I, my life is so good without him. Sure I miss male company sometimes and sex occasionally but never enough to make me put up with the crap ever again. And last time I saw fat ankles she was dancing the same menopause mazurka I was when she ran off with my husband. Now SHE looks 9 months pregnant and me, not so much! Life is indeed good!

  8. I'm 56 and I've also mostly given up on dating and really, it's a very good thing. I've decided that the significant compromises I made when I was younger are just not worth it at this stage of life. I've done the on line dating thing and while some of the men are nice enough, they're inevitably old...as in either years older (usually retired it seems with lots of time on their hands) or in such bad shape physically, emotionally, financially, or all of the above that my first thought is that they're just looking for someone to take care of them and I'm done being responsible for people who should be perfectly capable of taking care of themselves.

    I sound like a bitter old woman and maybe I am but it just seems like too much effort at this point in my life. I don't need a meal ticket, a caretaker, a parent for my kid, or any of that crap. I don't care about sex any longer so I don't want someone wagging his dick in my face.

    Sure it would be nice to have some ready companionship, someone who wants to get out and do something fun every now and again. Someone I can depend on to let the dog out, pick me up at the airport, listen to my gripes about work, prepare a meal every now and then. And yes, I'd be happy to do the same for someone else.

    I'm sure there are some great men out there who are kind, interesting, age appropriate, and independent but I'm not finding them here! And I'm really tired of looking and being disappointed.

    I give up!

  9. You know what I’m going to say, Jenny dear. But I’ll say it anyway.

    Make a list of the qualities you require (REQUIRE!) in a husband. The qualities that are NONNEGOTIABLE. There should be at least a dozen qualities on the list, because life is broad and deep, and a longer list forces you to think about more aspects of life with a man.

    Sidebar: If you’re going to look at your spiritual life, ever, now is the time. Because I know from all your past writing that you and your commenters are looking for good, faithful men. A life of faith is not required to be a good and faithful man, but it vastly increases the likelihood of such. And good, faithful men are looking for good, faithful women. This approach likely and rightly will include abstinence. A lot of our culture’s problems, including the hell it imposes on single moms formerly married to cheaters, stem from men and women accepting as “fine” wildly out-of-context behavior.

    Okay. Pray over your list. Give it to God. Go live your life looking at it from God’s perspective. If you can’t bring yourself to accept that there is a God, or a dimension of meaning and purpose to this life that transcends our crude understanding of it, just try to live for a while like there is, and watch for signs of it.

    Be the kind of woman who will attract the man whose qualities you have listed. Live by those qualities, and keep your eyes open for how the world responds to you as you do.

    I know! Your post was about how you can be comfortable and happy without a man. That is undeniably true. But if your interest in having a mate persists, drifting about vaguely hoping it happens one day, and focusing on the unsuitability of the bevy of losers who pass through your life, is a strategy for being a victim to life’s randomness.

    As you know, my first marriage ended in 1983 when my husband was unfaithful. In 1987 I made my list and stood by it through years of dating. In 1994 I met the man who met all my criteria and we married in 1996. He still seems like a miracle to me.

    Don’t drift. Focus on what matters. I do think the universe responds to aspirations toward the higher end of the moral scale.

    Badly written, I know ... sorry. These are not easy concepts to write about without triggers and sounding preachy.



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