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THE OTHER PORTLAND OREGON

September 28, 2025 by David Gillaspie

The other Portland once had a reputation as a place for rich hippies to retire young and send their kids to Reed College. If that was the 70’s those kids might be fifty or sixty years old; thirty or forty if they started a family late, or decided to have more than one family. Since […]

Filed Under: What's Up Tagged With: America, baby boomer, Baby Boomer blogger, Baby Boomers, blighted area, boomers, commander in chief, education, Eisenhower, family, hippies, kids, learn, millennials, Oregon, Oregon duck football, Portland, Portland Oregon, president, Reed College, retire, rich hippies, south portland, teddy roosevelt, travel

TRY ME? EVERY FATHER’S HOPE

September 25, 2025 by David Gillaspie

“I’ve got three boys,” a former football star said. “I’ve got to stay in shape because they’re going to try me.” Try me? Do we all know what that means? Probably not if you didn’t try your Dad. But you did. Right? You did? How did that work out for you? How does it ever […]

Filed Under: What's Up Tagged With: baby boomer, Baby Boomers, blog, blogger, boomerpdx, boomers, boxing gloves, dream, family, father, fighting, fitness, football, high school wrestlers, history, MARRIAGE, momma, mother, Oregon, Portland, Portland Oregon, skills, sports, story, strangers, tech talk, try, try me, try them, uppercut, wife, wrestler, wrestling, writer

THE ART AND CRAFT OF DODGING RESPONSIBILITIES

August 29, 2025 by David Gillaspie

Dodging responsibilities for a picture is not what my pal Bill Shonley and I do. He’s met a ton of people so getting a shot was no big deal. To him; it was a big deal to me. It’s one of my favorites. We’re both Blazers fans, though I’ve cooled off since Big Red took […]

Filed Under: What's Up Tagged With: Baby Boomers, bike, bike helmet, bike ride, bill shonley, BLAZERS, blogger, culture, dodging responsibilities, downtown, downtown Portland, enterprising blogger, helmet, keep riding, local culture, looking good, new bike, Portland, Roy Pittman, senior moment, sounding good, sports highlights, Steel Bridge, story, tilikum crossing, TOM McCALL WATERFRONT PARK, trail bike, warming up, wife, wife warning

MARRIED WEED COUPLE LOSING GRIP

August 13, 2025 by David Gillaspie

What happens when a weed couple changes their stance? When one of them decides to light up and the other doesn’t? If they are baby boomers, you’d expect them to do something baby boomer-ish, like write a letter to Dear Abby? No way. They’d sit down, after fifty years of marriage, and figure it out. […]

Filed Under: What's Up Tagged With: addicted, Baby Boomers, bong, bong rip, boomer problem, boomers, burn and learn, cannabis, dear abby, dear wife, direct action, Divorce, dope, drug addict, drugs, husband, lighten up, marijuana, MARRIAGE, married, nar-anon, observation, Oregon, oregon weed, Portland, pothead, rock and roll, sex, sex life, smoker, smoking, smoking marijuana, video games, volatile mix, wake and bake, weed, weed couple, wife

START THE HARDEST PART FIRST: BEER CULTURE

August 11, 2025 by David Gillaspie

Doing the hardest part of anything is not the opposite of doing the easy part. The easy part serves as a warm-up? Sometimes. But, do that and you might be too tired for the next part, which is also not the hardest. Like what? Take drinking beer for example. I live in a beer town, […]

Filed Under: What's Up Tagged With: beer culture, blitz brewery, booze, bottle of wine, dealer, drinking booze, easy part, hard, hard luck stories, hard part, hardest, hardest part, hawks view winery, home, NBA, North Bend, Oregon, part, police, Portland, Portland Oregon, small town boy, sneaking booze, sorry tales, start, start first, weed, weed dealer, wine, wine glasses

GROWN MEN GROW UP, EVENTUALLY

August 4, 2025 by David Gillaspie

Eventually, grown men grow up and get with the program. They try to resist, but as we’ve learned, resistance is futile. So turn your hat around, stop the online sports betting, and make someone proud. Put on your big boy pants one leg at a time and stand for something. But what? Let’s take a […]

Filed Under: What's Up Tagged With: adult male, ambitious, ambitious woman, bachelor pad, better example, better life, BOOMER, Coos Bay, grow, grow up, grown men, hippie, historical, long haul, message, new york, older adult, Oregonian, Portland, portland pad, pushed, short haul, sports betting, stoned, stoned hippie, test of time

PLANNED IGNORANCE? NOT SO FAST

August 1, 2025 by David Gillaspie

Planned ignorance is not a plan for everyone. Parents who complain about teachers when little Jimmy gets a bad report card? It’s not Jimmy’s fault and don’t you dare say it is; don’t even think it. And it’s not the parents’ fault. Just ask them. Better yet, check with parents whose kids are just starting. […]

Filed Under: What's Up Tagged With: big picture, brain development, careful parent, daycare, developing brain, high tuition, higher education, kids, learning envirnoment, NW Portland, Oregon, parents, plan, planned, planned ignorance, Portland, SE Portland, Southern Oregon, study hall, tuition, world events, young minds, young parents

MELANCHOLY NOSTALGIA? WHERE DO I SIGN

July 20, 2025 by David Gillaspie

Melancholy nostalgia is no one’s idea of a good time. Nostalgia alone is more than enough. Those ‘good old days’ never looked better until you start scratching around. Add a dose of melancholy to clear things up.

Filed Under: What's Up Tagged With: agreement, alphas, Baby Boomers, boomer elders, boomer phenomena, boomerpdx, common ground, education, facebook, MARRIAGE, melancholy, melancholy nostalgia, millennials, new ideas, North Bend Oregon, nostalgia, Oregon, Portland, Portland Oregon, real fun, remember, therapy, twitter, vulnerable age, writer, zoomers

LOOKING BACK TO SEE IF YOU WERE LOOKING

July 16, 2025 by David Gillaspie

I was looking back recently after hearing how great things used to be. Baby boomers had it so easy you could buy a house and two cars and a boat and send three kids to college on a part-time paper route for a weekly publication. As a result the entire generation grew lazy and complacent:

Filed Under: What's Up Tagged With: camel cigarettes, draft lottery, historical, historical references, hood to coast, looking back, looking back to see, marathon, Oregon, Portland, Portland Oregon, run away, running, Salems, smoke, smokers, sports, stepping out, stepping up, story, summer of love, tobacco, vietnam war draft

GOOD FORTUNE: ACCIDENTAL OR PLANNED

July 13, 2025 by David Gillaspie

My happy good fortune could never be planned any more than a shark chooses their favorite remora. It’s all been a long string of happy coincidence. Just another fat baby boomer taking up space in comfort and luxury. That’s me. How about you, same thing? Probably not, but check with younger people to know for […]

Filed Under: What's Up Tagged With: accident, accidental, America, baby boomer, bad boyfriend, blog, blogger, blogger attention, BOOMER, boomer blogger, boomers, Constitution, fortune, good fortune, history, Jakes, law, misfortune, Oregon, planned, Portland, PORTLAND BABY BOOMERS, Portland Oregon, shared concern, staged, unmasking, veritable quandary