7 Clever Tips for Winning Over Your Grandma’s Former Flame

As a young college-aged woman, you feel an unexplainable attraction to your grandma’s former beau, setting you off on a one-of-a-kind romantic journey. Sure, he’s in his eighties, but there’s an undeniable charm to his adult diaper elegance and that captivating Ben-Gay aroma. It’s a quirky twist of fate where the allure of experience meets the vibrancy of youth.

Tip 1: Dig into His Love for Classic Cars (and Duct Tape)

Start by showing interest in his classic car collection. It’s not just about the cars, it’s about the stories they carry. Talk about those quirky duct tape repairs he’s so proud of.

Then, bring up that hilarious episode where he lost his false teeth during a car repair adventure. It led to a week of liquid diet – blending his steak and potatoes to sip through a straw. You can’t make this stuff up!

Tip 2: Craft a Mixtape with Golden Oldies (on a Vintage Cassette)

Dive into the world of golden oldies and make a vintage cassette mixtape. It’s all about the charm of those crackling tunes. Think of it as a time machine in a cassette, with each song a ticket to the good old days.

When picking songs, aim for a mix of humor and nostalgia. The goal is to make him smile, not wince with heartburn. So maybe skip ‘Ring of Fire’ by Johnny Cash. It’s a classic, but the title might be a bit too on the nose after a spicy meal.

Wrap up the mixtape with some unexpectedly upbeat tunes. Throw in something like ‘Stayin’ Alive’ by the Bee Gees. It’s a song that’s both a nod to the past and a wink at staying youthful. Plus, it’s a great track for showing off those vintage dance moves, even if it’s just in the living room.

Tip 3: Send Mysterious Love Letters via Carrier Pigeon

Get creative and send love letters the old-fashioned way: carrier pigeons. It’s not just romantic; it’s a throwback to a time when love notes had wings. Plus, watching a pigeon land with a message is way more exciting than getting an email.

Keep in mind, though, he might need a magnifying glass to read your finely penned words. So, go big with the lettering. You’re not just writing a letter; you’re creating a billboard for Cupid. It’s the perfect blend of romance and practicality.

Imagine his surprise and laughter as he tries to decipher your billboard-sized love note delivered by a bird. It’s a story he’ll recount at every family gathering, making even the grumpiest uncle chuckle.

Tip 4: Organize a Shuffleboard Showdown

Spice up your courtship with a shuffleboard challenge. But this isn’t your typical tournament; it’s loaded with whimsical rules and a chance for some playful cheating. Maybe introduce a rule where every time a puck lands in a certain zone, you both have to share a funny story from your youth.

Add a dash of mischief to the game. Encourage a bit of rule-bending, like ‘accidentally’ nudging the board. It’s all in good fun and a chance to show off your playful side. Plus, it’s a great way to break the ice and share laughs.

Just remember not to schedule the showdown too late in the evening. You wouldn’t want his night medication to kick in mid-game and turn your playful banter into a sleepy mumble. Keep it light, keep it fun, and wrap up in time for his prime-time TV shows.

Tip 5: Adopt a Pet Tortoise and Name It After Him

Consider the unique idea of adopting a pet tortoise and giving it his name. It’s a charming gesture, showing you think he’s as timeless and enduring as this ancient creature. Plus, a tortoise is a symbol of wisdom and longevity, just like him.

Pick a name that’s a gentle nod to his mature years. How about ‘Methuselah Mosey’ or ‘Alderman Amble’? These names are tongue-in-cheek, capturing his seasoned wisdom and unhurried nature.

Let him know that, like the tortoise, he’s set for a long, fulfilling journey. You can cheekily add that you know the secret to a long life, and it’s definitely more exciting than prune juice or cough drops. It’s about enjoying every moment, just like the tortoise does.

Wrap up by saying that each slow, deliberate step of the tortoise is a reflection of his own steady and assured way of living. It’s not just a pet; it’s a living tribute to taking life one step at a time and savoring the journey, just as he has always done.

Tip 6: Hire a Frank Sinatra Impersonator

Consider the outlandish yet delightful idea of hiring a Frank Sinatra impersonator to serenade him. It’s a blend of nostalgia and humor that’s sure to bring a smile to his face. Picture the look of surprise and amusement when ‘Ol’ Blue Eyes’ starts crooning just for him.

Elevate the experience by gifting him a bottle of Jack Daniels. Encourage him to enjoy it in true Sinatra style. It’s a cheeky nod to the legendary singer’s fondness for the finer spirits in life.

For an extra twist, have the impersonator sing about the quirks of getting older. Imagine Sinatra-esque tunes about the joys of adult diapers, the thrill of prostate exams, and the ever-growing nose hairs.

Tip 7: Host a Grandmas’ Ex-Boyfriend Jell-O Wrestling Match

Envision a Jell-O wrestling match, but with a twist: it’s only for grandma’s ex-boyfriends. This event promises a unique blend of the ridiculous and the spectacular. Aging gentlemen, grappling in a pool of Jell-O, bring a whole new meaning to ‘senior activities’.

The highlight of the event? Your grandma’s most recent ex is, unknowingly, the star of the show. The match is secretly designed for his victory. Watch him navigate the wobbly battleground, emerging as the Jell-O champion amidst cheers and laughter.

Seize the moment of his triumph. As he stands there, victorious and Jell-O-drenched, ask him to be your boyfriend. Just ensure his hearing aid is turned up so he doesn’t miss your sweet proposal amidst the uproarious celebration.


Your grandma clearly has great taste in men, and if you’re eyeing her latest ex, it’s all about staying sharp and doing whatever it takes. Think of it like a spider strategically weaving her web, ready to charm him into your world with creativity and flair. Be ready to swoop in with your unique charm, ensuring he falls for you just as easily as he did for her.


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