My Next Leap is, among other things, some observations on being 60 and single in south Florida in the late 2010s. MyNextLeap, by the way, was once the name of a seed stage venture I founded that was focused on the nexus of workforce development and wellness. That, around 2007-8, happened to be a gap in the human-capital space once defined for me by a smart Minneapolis-based venture capitalist. I took the idea and ran with it except that it happened that that year I found myself divorced, moved and rocked by the global financial crisis. No more desire for venturing... Since the only IP in the venture was the name and some powerpoints, I sold myself the name, shook my own hand, handed myself a dollar and now use the name here for this blog in a blog. The game here is to describe (to at least myself) some of the absurdity, angst, marginal cost, social weirdness and other whatevers of having only 25 years (or so) left to get something right that should have been gotten right a very very long time ago.
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12/18/18 - I have to say this: while I like to hear this in general as much as the next guy, I also have to say that if I hear the word "sweet" one more time, with nothing more than a pat on the head and that little puppy talk voice to back it up...even if that voice is implied, I think I'm going to throw up.
12/14/2018 - One might think that by 60 one would have the skills to not be friend-zoned. One would be wrong. To person A: you're so sweet...and nice...and we'll be such special friends forever; I'd hate to ruin all that special-ness with something like sex or, god forbid, love. To person B: I want to learn to love you, sleep with you, and then convince you to move away with me so we can live our lives together deeply. Person A feels aggrieved but told not to be because Person A is "special." Person A then vows to never be nice or sweet or special. Again. Ever.
9/23/18 - I thought of an unfortunate metaphor today for what I've been trying to do: auction. This is unfair because it looks like it diminishes the humanity of the people I am trying to date. But really the metaphor is more for me than them. It goes like this: instead of auctioning myself to high bidder (I'll carry the metaphor on that in a second) I have been consistently auctioning myself to the first bidder...with predictable results. If we define highest bid as not money or attractiveness or even intelligence, but heart -- the emotional depth of their kindness, compassion and trust -- then it is self evident that I have been playing one seriously long game of "opportunity cost." That's a bad game to play especially as an endgame.
9/22/18 - When in a relationship or maybe just out of one, when looking back over time, it always has the hard, solid look of inevitability. But then you turn around, face the future, and realize how elusive it all was, and is...how soft. There's nothing there to hold onto but what's not there, the unknowns, the untruths, light to hard fraud, fake ages, fake pictures, bad faith in the motivations, ghosts, missing teeth, missing sanity, the indecisive, the intemperate, and the unprepared and the unready. With each uptick in hope you realize that progress, the upticks, are mostly an illusion. It's a little like trying to hold water in your hand. It all slips through your fingers while you keep trying to convince yourself that this time it's different. This time it's going to solidify into something good.
9/16/18 - Over the last 60 years I have had my fair share of first dates. "Only one" first date over that time would have been nice but we have what we have. But then again, over that time the most attractive thing I've seen without exception (well, except maybe one) were the tears my date shed on our first date this Friday. We were talking about family or children and something we said made her voice catch and her eyes well up a bit. I'm sure she was mortified at the time (and no, she didn't weep at the horror of the mere sight of me) but when she cried her humanity exploded into plain view. All of her secret inside vulnerability, sensitivity and heart were exposed to the full light of day for just one moment. This is rare in general; more so in Florida. The fact that she was extraordinarily beautiful -- think young Michelle Pfieffer -- on the outside was irrelevant at that point. The inside stuff is another thing altogether. My guess is that she's going to take a pass on me but it's unfortunate because she looks, to me, like a once or a twice-in-a-lifetime thing based on some pretty thin info. She has no idea (yet?) what I'd give for what I saw in that moment. We'll see.
9/15/18 - Getting one's hopes up too soon appears to be the second cruelest trick the universe plays on us in the late-middle-age dating game. Number one is trust-betrayal but that is another story for another time.
12/14/2018 - One might think that by 60 one would have the skills to not be friend-zoned. One would be wrong. To person A: you're so sweet...and nice...and we'll be such special friends forever; I'd hate to ruin all that special-ness with something like sex or, god forbid, love. To person B: I want to learn to love you, sleep with you, and then convince you to move away with me so we can live our lives together deeply. Person A feels aggrieved but told not to be because Person A is "special." Person A then vows to never be nice or sweet or special. Again. Ever.
9/23/18 - I thought of an unfortunate metaphor today for what I've been trying to do: auction. This is unfair because it looks like it diminishes the humanity of the people I am trying to date. But really the metaphor is more for me than them. It goes like this: instead of auctioning myself to high bidder (I'll carry the metaphor on that in a second) I have been consistently auctioning myself to the first bidder...with predictable results. If we define highest bid as not money or attractiveness or even intelligence, but heart -- the emotional depth of their kindness, compassion and trust -- then it is self evident that I have been playing one seriously long game of "opportunity cost." That's a bad game to play especially as an endgame.
9/22/18 - When in a relationship or maybe just out of one, when looking back over time, it always has the hard, solid look of inevitability. But then you turn around, face the future, and realize how elusive it all was, and is...how soft. There's nothing there to hold onto but what's not there, the unknowns, the untruths, light to hard fraud, fake ages, fake pictures, bad faith in the motivations, ghosts, missing teeth, missing sanity, the indecisive, the intemperate, and the unprepared and the unready. With each uptick in hope you realize that progress, the upticks, are mostly an illusion. It's a little like trying to hold water in your hand. It all slips through your fingers while you keep trying to convince yourself that this time it's different. This time it's going to solidify into something good.
9/16/18 - Over the last 60 years I have had my fair share of first dates. "Only one" first date over that time would have been nice but we have what we have. But then again, over that time the most attractive thing I've seen without exception (well, except maybe one) were the tears my date shed on our first date this Friday. We were talking about family or children and something we said made her voice catch and her eyes well up a bit. I'm sure she was mortified at the time (and no, she didn't weep at the horror of the mere sight of me) but when she cried her humanity exploded into plain view. All of her secret inside vulnerability, sensitivity and heart were exposed to the full light of day for just one moment. This is rare in general; more so in Florida. The fact that she was extraordinarily beautiful -- think young Michelle Pfieffer -- on the outside was irrelevant at that point. The inside stuff is another thing altogether. My guess is that she's going to take a pass on me but it's unfortunate because she looks, to me, like a once or a twice-in-a-lifetime thing based on some pretty thin info. She has no idea (yet?) what I'd give for what I saw in that moment. We'll see.
9/15/18 - Getting one's hopes up too soon appears to be the second cruelest trick the universe plays on us in the late-middle-age dating game. Number one is trust-betrayal but that is another story for another time.
9/10/18 - I spend a lot of time doing actuarial math. I don't know why. But from that sordid effort I know that I have about 25 years left give or take based on the probabilities involved. Fine, say 25. Given 25, I know that the last 5 will be suckier than the first 5. That means I know that if I want to change things, since time is short and late time is worse than near time, I better deal with what I am dealing with now. I once calculated the marginal cost of waiting here. The point was that the cost of not making changes goes stratospheric the longer I wait. "Bias for action" as my now-dead former boss with the now meaningless giant pile of money used to say.
9/9/18 - What was once a vast landscape of dating choice when young has now seemingly tended towards binary now that I'm old. By that I mean that when one is in one's 20s or even 30s the vast middle ground of dating and relationships is wide open: hookups, short term deals, casual indeterminate things, delayed commitments, fuzzy arrangements, long term connections that go nowhere... whatever. Now at 60, that middle ground has almost completely gone away. If we set this up as a spectrum from left to right where single solo no-connection with anyone ever again is on the left (a growing appeal, the demands of relationships have very high costs) and committed, all-in, full heart, true-love total-caring for someone with what's left of a lifetime is on the right, then we can say that things are tending towards the left-right binary rather than the middle. And maybe that's good. But that simplicity obscures things. If I were to choose left, which I may, then the middle ground might still be in play. I mean, I'm not a monk...yet. On the other hand, if I choose right, which I actually still want more than you can possibly imagine, then we have to realize that one doesn't go full right on the first date. It takes time and several dates or even several people over several rounds of trying. i.e., it's complicated. And the main complicator, by the way now, is time. Being 20 with another 70 years to go is a wide open proposition. Being 60 with maybe another 25 years to go is another thing altogether. Time is getting short. And, I hate to mention, the next 25 years is not a monolith. The last 5 of those 25 will be suckier than the first 5. That means that the pressure is on to deal with my remaining time right now. An that, frankly, really is a lot of pressure.
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