Generational Throwdown Part II – Generation “Y Not?”

I started my thirties dating career (upon becoming single a couple weeks before my thirty third birthday) thinking I’d find the perfect thirty three to thirty eight year old man within six months.  I was a catch, so it all seemed obvious to me that I was on the right path after a righteous breakup.  I literally laughed in the faces of younger men who approached me.

This is a true story.  A couple years ago, a hipstery younger guy with nerd glasses and a vintage snap front shirt earnestly approached me at a bar, inviting me to the dance club where he and his friends were headed. I laughed self-consciously and said “oh, I can’t stay out late tonight, I really want to get up early and go to the farmer’s market to get some tomatoes.”  The expression on his face didn’t stop me from saying “I’m older than you, we probably have different priorities.”

He managed to take it in stride and throw it back in my face at once.  “You really shouldn’t judge any guy who’s younger than you just because of his age.”

“Oh, so you are younger than me!  I knew it!” I actually said this flirtatiously.  No actual ages were exchanged (though I did find out later I was correct about his twenty seven year old status – an age I have no problem with these days now that I’m two years older).  The guy walked away.

I hope this story does some justice to younger guys actually being pretty cool.  A lot of being single is a numbers game, and desirable single men my age are like ladyslippers, the endangered flowers that grew in the forest behind my childhood home in Massachusetts.  You’d find just one or two a year, beautiful and seemingly perfect, but you were unable to pick them due to laws protecting the species.  They’re meant to be married to the woods, or enjoyed only through admiration.


Ladyslipper Photo Credit:


Photo: Younger Guys Are Actually Pretty Cool.  (Ledger – rest in peace – dob 4/4/79, Watts, dob 9/28/68.)

I have two girlfriends involved in serious relationships with men nine to ten years younger than they are.  As my friend with a live in twenty seven year old boyfriend taught me, I preach the gospel of “Generation Y Not?”  My experience shows that Millennial men are more open to dating an older woman than guys my own age are (which would make them more open to dating older women than guys in their thirties are open to dating women their own age).  Online dating sites are full of guys in their thirties whose age range ends two years younger than themselves.  I’m certain this has to do with impending reproduction.  The guys in this late thirties age group believe they have until their early forties to really settle down, when, if they didn’t snag a woman two years younger yet, they will try to date women in their early thirties (childbearing age but have a couple years left to get to know the guy).  Those women will wrinkle their noses at the appearance of never married forty-somethings in their inbox.  And, they’ll ignore them because plenty of twenty eight year olds are contacting them too.  I know this from experience.  It may, in fact, be a Gen X type problem.

The icky parts of the thirty and forty-something guys only make the young ones more appealing.  I don’t know if Millennial guys are less threatened by women like me, or it’s just that older woman/younger man relationships are perceived as sexy (see celebrity examples), or that I don’t, right off the bat, look my age.  But my experiences have been largely positive.  Maybe Millennial guys have had access and exposure for so long that they’ve just evolved more.  Or maybe it’s that they know they have such an uphill climb in the long run that they’ve stripped down to what’s really important.  If you graduated from college with one of the worst financial crises in history going on, a black president, Cher’s transgendered daughter (now son) on “Dancing with the Stars”, and mass shootings occurring so frequently they cease to be terribly surprising anymore, wouldn’t you have some sense of gravity in your life?  Would you really sweat the small stuff like the age of your girlfriend, or at least the age of the woman you are dating that month?  This gets so confusing when you factor in Smartphones and Tinder (see future post, “Tinder’d”).  I find Millennials at once delightfully expansive, and also frustratingly flaky and afflicted with “shiny object” disease.  Or is that just their youth?


Photo: Remember this Millennial/Kinda Gen X Pairing?  (Gosling, dob 11/12/80, Bullock, dob 7/26/64 – i.e. not quite Generation X but close)

Dating younger/Millennial guys has been helpful to me.  I’m not sure what I’m more enamored with – their thick, shiny hair, or their potential.  I whined to my sister about one of them, “he’s too young to have failed yet.” I think this is due to the slightly-younger-than-me generation being, largely, quite a bit more coddled by Mom and Dad than my group.  I had screwed up royally, in multitudes, by the time I was twenty five.  And wouldn’t trade it for anything.  In their youthful presumption, none of the younger guys have realized how many stories I had for them if they’d ask.  They thought they already knew it all (or didn’t care).  While my demographic has become old news, theirs is “the future” and the target of marketers and the media.  They even have their own TV network (, while I can’t stop watching aspirational reality on Bravo.  The world is truly their oyster.

I felt jealous of one of my Millennials.  He was so young that he still had acne in some of his Facebook pictures.  He was full of adventures and was well funded, but he didn’t have what he wanted and was in search of a career that would fulfill him.  I was inspired by his plans and enthusiasm, even about the things I’d already done.  The next younger guy was full of an earnest desire and like for me.  It would have freaked me out from a thirty five year old, but was deliciously cute and sincere in a less experienced twenty eight year old.  It was obvious he didn’t have the baggage that made my typical dates feel so formal.  I let myself enjoy every bit of his unguarded and foolish expression.  While it didn’t last long, and I ignored many warning symbols of those who rush in, it reminded me I could feel something other than judgmental and self-protective.  In the “I can see you ten days from now for two hours” world of professional thirty and forty-somethings, these guys made me feel young again.  I remembered that my life isn’t over.

I’ve been scolded by my mother and sister that I’m “setting my sights too young”.  They don’t realize that I haven’t set my sights anywhere – this is just what is in my sight.  If I want to date a guy my age, or in his early forties, I’m going to have to break up a marriage or start hanging out at playgrounds hunting divorced guys.  They’re a lot more work to go out with, and ultimately you might not enjoy your time with them quite as much.  The younger guys I’ve hung out with aim to please in a way that accomplished guys with money do not.  Perhaps this has to do with the belief that you have something to prove, rather than the belief that you’ve already proved it, and any woman should be glad to have it.  I enjoy “it” being proved to me over and over again (wink, wink).

I’ve realized, via dating them, how far behind me the under thirty guys are in some cases.  Regardless of maturity relative to the age difference, they are just getting their careers started (much like I was at twenty eight in Bush America).  It’s only in the last few years I’ve felt that I’m taken seriously professionally and felt like a grown up.  Millennial guys just south of thirty largely aren’t there yet, and won’t be for a while.  I’m trying to recalibrate my expectations – that I may not be living in a large suburban house (when did I ever really want that anyway?) and be able to retire with my home paid off and money in the bank like my parents.  I may only have one child, or no children, and I will probably be someone’s second wife.  I don’t have to drive new cars and I can learn to live within my means.  Like many Gen Xers I started out thinking I would have all these things.  I was sure I’d direct a film by age twenty seven (seemed reasonable for a twenty two year old living in L.A.) and when that didn’t happen, I kept recalibrating my career goals over and over again.  After thirty you recalibrate your financial and relationship expectations.   So, I’m lucky I didn’t lose money in the housing crash like those a little bit older, or more settled than me.  I kind of have a second chance to figure it out now post-2008, and without the responsibility of having children.

For Millennials just starting – they can change their expectations now (and the twenties are supposed to be your most important decade according to a book I want to read, “The Defining Decade” by Meg Jay).  So, while I missed the boat of my twenties already, I feel like I’m just starting too, and my options are limitless… at least for a few more years.


Photo: Possibly NOT taking advantage of “The Defining Decade” in a positive way at twenty seven.  P.S. – Has nothing to do with the mustache guy.  For real.

I think the Millennial’s culture will change people’s ideas of what adulthood means.  To my mind, this will further develop the Europification of the U.S. that’s already happening now that everyone wants to live in the city.  I like this, and I like minimalism in living (but not in clothes shopping whenever possible).  Europeans have known how to live small for years.  I don’t know if I consciously chose this path for myself, but it seems like my path right now.

Recently I had dinner with a twenty nine year old that made me think I was done with younger.  He was interesting, intelligent, had been in the Peace Corps, all things I find very attractive.  The conversation was lively, and he was sincerely sweet.  But I really didn’t want to see him again.  ”I just want to date someone who knows what new wave is and doesn’t have a roommate,” I thought, generalizing what was ultimately a personal experience.

Confronted with multiple Millennials on a Friday night, I again remember how much I like them and their charming attentions via text.  Still, many things separate me from this younger generation that I can’t change, like the media will stop making movies about people my age as the years add up.  I want to go out with someone born in the 70s who remembers watching early MTV.  Really… I do.  But until that happens, I’m not going to turn down what’s right in my face, filled with joy and happiness, and sporting a full head of hair.  How can I?  I am young.

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