I'm not sure whether the deceptive decline started with his parents or grandparents, but Alan's parents got married and settled in a bustling Jewish area of New York. They created the ideal nice 'n' tidy American family: one boy and one girl.
It was easy and enjoyable to be part of the thriving Jewish -- though not so religious -- community in that area.
The boy, Alan, grew up and met Marybelle in college. Marybelle, long disillusioned with Christianity, enjoyed the watered-down Jewish beliefs and practices and was pro-Israel (which was the norm in America back when Israel was seen as the poor, harassed, struggling underdog constantly on the verge of total annihilation).
Marybelle happily underwent a Conservative Jewish "conversion" and was embraced as a Jew by Alan and his family because their Conservative rabbi declared it all to be totally kosher. (After all, only fanatics wouldn't approve of the delightful Marybelle and nitpick about fuddy-duddy details like Shabbos and taharas mishpacha.) Marybelle remained an enthusiastic synagogue attendee on Saturdays where she often sported a pink & white kippah, and she joined the synagogue sisterhood, and proved herself a proud supporter of Israel (as long as the pro-Israel politicking never went too far Right).
Alan and Marybelle lived a happy life together and were some of my favorite adults as a child. (Marybelle is indeed a delightful and caring person.) They both loved children, yet they never managed to produce children. Alan's one sister also married a non-Jewish man and never managed to produce children either.
At the age of 70, Alan came to Eretz Yisrael for the first time. He was recovering from several bouts with illness and organ failure, but feeling better, he figured this was his chance to finally visit the Land.
There's No Place Like Home -- Literally
The conversation ebbed and flowed because Alan couldn't stop himself from pausing to take in all that was around him, slowly turning his salt-and-pepper head this way and that. He breathed in deeply and his eyes were aglow with dreamy bliss.
Though always a cheerful person, I'd never seen him look so serene and blissful.
But it was deeper than that.
His face was aglow with the look of a man who'd finally come Home.
He'd finally found his place, even though he never realized he'd been searching for it.
But it was too late.
Had Alan made different choices, I could see Alan fitting into one of the Anglo communities of Ra'anana or Ramot of the Eighties.
But instead, Alan died not long after that visit without any remnant, neither for himself nor for his parents.
And his sister never left a remnant either.
That was it. End of the line.
Shiny Happy Deceptions
Perhaps Alan's parents' line wouldn't have ended had they gone beyond the oh-so tidy one-of-each and had more children (if they could, I don't know) who might have had children.
And had Alan's parents sent him and his sister to a teacher or an institution that could've taught them real Jewish values, perhaps Alan and his sister would've made different decisions, decisions more conducive to the Jewish soul.
And perhaps had the Conservative rabbis not been so gung-ho about masking intermarriage via fake "conversions," Alan's parents might've thrown up more resistance. And perhaps Alan himself, who obviously did care about marrying a Jew, wouldn't have been duped into the feel-good act of marrying a non-Jewish woman because of his certainty that she now was Jewish...a woman who, though delightful, wasn't his real zivug.
And maybe Marybelle herself, who did seem to have a real attraction to Judaism, would've either discovered Torah-true Judaism and followed through with a real conversion or would've become a righteous non-Jew following the 7 Noachide Mitzvot. (Although this is getting to deeply unknowable territory, with regard to what Marybelle's lifelong attraction to Judaism really means.)
Needless to say, there are no guarantees.
After all, there are frum Jews who go off the derech and marry out, there are Jews who never have children, and so on. (Although it is a comforting Jewish belief that one's deeds are offspring -- like children -- so a barren Jewish couple can take comfort in the mitzvot they've created, even though childlessness is still an admittedly painful nisayon.)
But without the all-smiles reassurance from the Wishy-Washy Whitewashing movement, then Alan could've had a fighting chance.
But it's over now.
End of the Line
One is dead and the other is dying.
Others have more non-Jewish grandchildren than Jewish children. (For example, 3 Jewish grandchildren from one child and 5 non-Jewish grandchildren from the other from different marriages.)
And this is also due to other factors growing in society at large, such as deciding against getting married or having children, never getting around to having children, or waiting so long to have children that it may no longer be possible without a lot of medical intervention.
Or skipping the marriage aspect entirely and finding a donor to have a baby on your own.
And if you're an assimilated Jew, then these often are your children.
There's not much choice; this is the society nowadays.
When All Hope Really is Gone
Because when I first became frum, I focused on having a good relationship with family and old friends of family.
And it felt good to do my part, like davening that everyone does teshuvah, and that things work out well for the very likeable non-Jewish partner too.
And I even tried talking to/corresponding in a really nice (too nice actually, in regrettable hindsight) approachable manner with a couple of Conservative rabbis, but despite their friendly open facade, they proved extremely close-minded.
If you become frum, then that circle of family and old family friends often ends up meeting your frum circle. In my case, all the frum people they met were very likeable and approachable.
But all those years of niceness and approachability never seemed to have any effect.
Then you see everyone getting older and -- let's face it -- more decrepit.
And the truth starts to sink in: It's too late.
But you still have hope for the pintele Yid to come galloping through like the Calvary at high noon.
And then the Jew keels over and that's it.
Calling a Spade a Spade
Because they have good intentions and a minority of their members stay connected to their Jewish rituals (albeit the watered-down version of them) and marry Jews, they feel that's reason enough for hope and good cheer.
Yet I'm seeing death.
That generation raised on the feed of synthetic Judaism is dying and they're dying in the most spiritually desolate way possible: without a remnant of Jewish deeds or Jewish children.
May Hashem atone for us & gather us back to Him with Revealed Compassion.