Dating Again After Twenty-Two Years


Online dating

Being alone was cake compared to re-entry into the dating world after a 20 year marriage.

I was so naïve when I started my foray into being alone, it should be no surprise that cluelessness defined my approach to dating.  It was practically my post-separation/divorce M.O.  When I started dating again, here was what I worried about:  will anyone find me attractive after all these years, how will I find people to meet, and will I be able to form a successful relationship with someone new?

The answers to the questions above were:  yes (mercifully some men still found me attractive), online (where I would have to meet men, not the gym, bars or school, unless I wanted to now date my students), and yes (I will eventually be able to form a new relationship, but that is a subject of another blog).   Wheewwww.

Here is what I should’ve worried about but had no inkling:  what were the mating rituals of the 21st century (incredibly it was the last century when I was last single), what did the modern man look for when meeting single women, and what etiquette, if any, was expected with these new mating rituals?

Of course, these all came as a shock to me.   After all, much had changed in the 22 years since I was last footloose.  The year I was last single, Anthony Kennedy was appointed to the Supreme Court, the Soviet army withdrew from Afghanistan, gas was 91 cents/gallon (you read that right), the first transatlantic fiber optic cable was installed, and Sonny Bono was elected mayor of Palm Springs, CA (Generation Nexters:  google it).

The internet was not widely used in 1988 and has profoundly influenced modern mating rituals.  The upside of accessing thousands of men instantaneously online had a major downside: they could instantly access me.   I wished to browse from the anonymity of my computer and in the comfort of my jammies.  I wanted to casually peruse the profiles of single, (well turns out, kind of single), attractive (well, from this side of sunglasses), successful (well, success is relative), interesting (well…) array of motorcycle-riding, moonlight walk-loving men and ever so slowly dip my toe into that water.  But the trouble with these online dating websites was that they required that you registered to browse.  In what seemed a blink of the eye, I was receiving emails and “winks” from men literally all over the world (well, so some of them claimed).  This I could handle, because I could choose to just delete or ignore these requests.

But unbeknownst to me was the instant messaging function, where in a heartbeat, you’re chatting live (Live!) with some stranger.  When this first happened, I sat there, paralyzed and terrified.  “Ahhh!!!  What do I do???”, I shrieked to myself.

“Answer him!”, I shrieked back.

“Thank you for messaging  me but I really am not prepared to IM with a stranger”, I typed calmly.  Eventually I gathered my courage and began to email and IM both to and fro with strangers.  After all, I took my time responding and it still was a relatively nominal commitment.

Inevitably though, someone wanted to talk on the phone (The phone! Live!).  “What do I do???”, I shrieked to myself.  “Don’t talk to anyone, you’re not ready!!!”, and so forth.  The same cycle of terror/calm ensued with the phone, and then with the first few coffee dates, before I gathered my meager courage to talk or meet, live and/or in real time.

The second area where I was clueless then subsequently shocked, involved what these men were looking for on the online forum.  I intentionally phrased the subject this way, committing only to the “men” and “online” descriptors because desirable qualifiers such as “single” or “relationship” were purely optional.  Married men, thrice-divorced men, never-married men, older (by a lot) men, barely-legal young men/boys were all online looking for something.  As a 40-something I was not prepared to hear from that 70-something and even less from that 20-something.

Some men were looking only for sex.  To their credit, a few were completely transparent about it.  Others evaded the issue but dropped hints, like sending explicit photos or talking about their sexual preferences.  A grenade is more subtle.  Some were looking for the equivalent of phone sex, others were ready to drop everything and come right over.

There were scary men too.  Some men became belligerent, angry or abusive if, even online, you didn’t do or say what they wanted.  There were those that refused to send a picture or tell you their full name, but expected you to meet them without providing any prior identifiers.  Some men were looking for relationships spanning the whole range: some purely platonic, to a couple who felt we were “in” a relationship with the first email.  Fortunately there were also men operating in-between those two extremes.

In retrospect, I believe I was still in denial regarding the reality that entering the dating game meant I might end up being with someone new.  However, I learned to work through my terror, to enjoy dating again, and eventually to not take any of it too seriously.  Having expectations more consistent with the 21st century improved my attitude considerably.  I met a wide range of yes single and yes successful (yes) men, and every meeting was interesting regardless of the outcome. Finally I learned how I fit into the reality of the world of single people, and how to be patient with myself and forgiving of my uncharacteristic emotional volatility.  Venturing into this entirely unknown universe revealed a side of myself I was unacquainted with; successfully navigating that venture gave me the confidence to go to the next logical step – a new relationship.

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