Dating Online In Your (late) 40s; Life In The Discomfort Zone

If you ever want to test your self-confidence, try dating in your late 40s.

The last time I dated was 23 years ago. I was coming off an ill-fated two year marriage to my college sweetheart, all of 23 years old and on the prowl. The dating world was a tad different back then. 

In 1993 we dated the old fashioned way: I would take my nimble, dewy complected self to a bar with a gaggle of my friends, and we'd drink and flirt with guys.  Maybe we'd get a phone number, which we would write on a napkin and stuff in our purse, because cell phones were big clunky things that a few rich people and business executives had installed in their cars. 

Then we'd go home and angst over whether to call him, or wait for him to call. If we were feeling particularly obsessed we'd come home from work and dial *69 to see if we missed his call .  Or we'd call him to see if he was home and hang up, because caller ID had yet enter the scene and foil the plans of stalkers everywhere.

And if he didn't call? Oh, well. We had decades of youth stretching out before us; there was plenty of time and oh-so-many fish in the sea.  We'd simply slip into a little black dress or a cute pair of jeans that hugged our curves in all the right places, take our hopeful visages, toned legs and perky breasts out to the bar and wait for the boys to flock like bees to honey.

For some of us - like me - the mission was to find The Guy. I wasn't a serial dater; I've always been a monogamous type. I sought stability, predictability and loyalty. I was looking for a good future husband and father. Of course he'd have to be hot, though. And tall. And funny. And smart. 

I could afford to be picky, because I was all those things: funny, smart, tall and - although I sure didn't think it at the time - I was hot. 

And, lucky me, I met him by age 24. He hit every single "must-have" on my list. Sure, he was a tad commitment phobic, but I could work with that. I had all the time in the world, remember? And I was patient. I could wait forever for The Guy.  Forever turned out to be seven years, before he looked at me with fear and excitement in his eyes and said, "You're gonna marry me, right?"  The rest, as they say, is history. 

Or so I thought, as I skipped merrily into middle age thinking my dating days were behind me forever.  

Crash landing in the dating world in 2015 felt like time travel, but where the protagonist doesn't simply plunk into the future an adorably befuddled but still-youthful version of herself.  Instead, she wears every inch of the 22 intervening years.

So how does a 46 year single working mother date?  A sober one, at that? Long gone are the bar days. And even if I did go to bars, far in the rear view mirror are the times when all that was required to garner male attention was to walk into the room. 

Dating, nowadays, is (mostly) online. I don't think anyone has scribbled a phone number on a napkin since 2002. 

If you find yourself freshly divorced in your 40s, startled and blinking in the harsh light, I have compiled a timeline for you, so you know what to expect. 

You're welcome.

The first step is to join every single dating site you can find, because you know nothing about anything and casting the widest net possible seems like a good idea (you will live to regret this decision).

Then you create your online profile. You search for pictures that make you look good, but not *too* good because you don't want him to be unpleasantly surprised if you meet in person.  You find that full-body shot that still looks like you, but maybe with an arm or a kid or a chair placed strategically in front of your less desirable parts.

Then comes the dreaded self-description. You answer the basics: height/eye color/lifestyle choices/employment.  Then this: what is your body type?  Are you (a) slim (b) toned (c) athletic (d) average (e) a few extra pounds (f) Overweight?  Was is "average" anyway?  Unless you are decidedly in the first three, everyone picks (d).

Even worse than the photo selections is the dreaded self-summary.  Can you imagine if in order to grab someone's attention in a bar you started with this buzz-kill opener:  "Describe yourself in 1000 characters or less!  Make sure to include who you are and everything you've ever wanted!" 

If you survive the first two with your sanity intact, you get to describe what you're looking for in a mate. This will be a tad depressing, because long gone are the days when you could prattle off this list fully expecting to check every box.  You'll manage to craft an eloquent description nonetheless, but what you're really saying, you'll come to discover, is this:  "Not still married. Not looking for just a hook-up. Not living with his mother. Hair a plus".

You upload all of this information onto about six dating apps, and then obsessively check all of them all the time.  You swipe and click and wink and message your way to a first date. 

The first time you dress for a date you will agonize, try on everything you own, fling yourself on your bed, curse your middle aged body and wonder when it was that your boobs fell about six inches.  It will dawn on you, with horror, that if the relationship progresses someone will see your c-section scar which has evolved into a kind of reverse tummy-tuck (producing a jiggly pocket of skin you can't lose no matter how many sit-ups you do), your love handles and that mole you never had removed (because only your husband saw it, so who cares?). This thought will make you want to die, but you'll persevere. 

You won't want to look too nice (desperate) or too casual (slovenly).  It will take hours to find that outfit that says: "I tried but not too much".  You will then proceed to wear this outfit on every first date. You will wear this outfit a lot, because you will mostly go on first dates. 

You will quickly realize that everyone isn't who they appear to be online. There will be the date where the moderately handsome man, according to his profile pic, turns out to be at least forty pounds overweight and missing a couple of teeth. Oh, and an eye.  There will be the date that starts as a casual stroll in the woods and turns into a hike worthy of its own mini-series, and you are wearing sandals and striving valiantly to appear you aren't slowly dying (after all, you said you like exercise in your profile).  

You will learn most guys say they are looking for a relationship, but what they really want is to hook up.  You won't be able to decide if this horrifies or flatters you.

The first few times you meet someone in person you'll be nervous and coquettish. This will not last. You won't become jaded, exactly, but you will discover you know in about thirty seconds if you're even remotely interested, and become skilled in disengaging quickly (your go-to will become the fake text from home).  

It will take a while, but the day will come when you are totally interested after that first sniff-test coffee date and he isn't. 

Here you will realize how much stalking has progressed since 1993.  You will be able to see when he is on the dating site, presumably chatting with young, supple women who don't have stretch marks. You'll debate how often to check his profile, because of course he can see when you do that. All your messages back and forth are still there, frozen in virtual eternity, mocking you.  You may even find his Facebook page and die a thousand deaths when you see him with his arm around a gorgeous young blond. 

You won't be able to decide if you really like him or if you're just obsessing because he didn't like you.  

This may even happen to you a few times, and you will spend a few dark nights of the soul thinking you will be alone forever, that you're uninteresting and unattractive. You'll curse your ex, who enjoyed the last years of your youthful self and left you with this unrecognizable old-person's body. 

You will delete your online accounts in a snit-fit and curl up with Netflix and ice cream for a while, but eventually you will go back. Perhaps more selectively this time, on the more reputable sites.  You will become more adept at screening out the undesirables. You will no longer answer every message you get because you feel badly if you don't. You won't feel as guilty if you meet someone in person and there is no click.  Instead of lying your way out of it, you'll learn how to disengage with honesty and compassion.

And one day you'll wake up and realize you aren't obsessively checking the sites anymore, and that you are okay whether or not someone likes you back. You will have reached way out of your comfort zone - several times - and emerged okay.  You'll have ample opportunities to work on your boundaries, and will eventually learn not to go on a second date because you feel badly letting someone down.  

You won't spend every minute of every date wondering if he likes you.  Instead, you'll be thinking about whether you like him. 

You will come to embrace your beautiful, battered body, and you won't care as much about your perceived flaws.  You'll realize you're still pretty hot in your own unique way.

When someone doesn't like you for exactly who you are, it will no longer obliterate your self-confidence. You will learn to accept that you don't need to be all things to all people.

Most importantly, perhaps, you will come to know that you don't need everyone to like you. You will believe, for the first time in your adult life, that you don't need to be anyone's other half to be okay. 

This whole excruciating process? It will lead you back to you.