Daughter Decides to Test Her Mother’s Young Gold Digger Boyfriend – Story of the Day

Shirley got herself a new boyfriend—much younger than she was … but her daughter Ashley realized something was off, and she was determined to find out the truth.

Are you serious? No way! Are they actually reducing your vacation to just eighteen days per year? Girl, you really need to …”

Ashley was just on the phone with her best friend Kate when her mother stepped into the house—she just came back from her vacation in Greece. She could see it in her eyes that something happened during that vacation—something pleasant, for it’s been a while since she’d seen her mother with that radiant smile. Not since her father passed away, anyway.

Shirley was already in her mid-50s—the golden prime of her mid-life crisis, evident with her obsession with “Eat Pray Love” and exotic yoga sessions and outrageously overpriced hair makeovers, at an average interval of roughly twice every half a year. But money was never a concern, for she could always afford it with her late husband’s handsome inheritance.

Hey Ashley, I booked a table at a restaurant tomorrow night. I want you to meet someone,” Shirley said.

Who could that be?

The next day Ashley found herself in the restaurant, a French establishment in the heart of the city where a starter cost upwards of $20. It has to be an important dinner then, even for her mother’s usual standard, Ashley thought to herself.

And in came Shirley and a young man, all dressed up for the occasion—as best as he could, at least. He wasn’t a bad-looking man himself, but his sense of fashion definitely left something to be desired.

He was donning a tightly fitted blazer that left a big crease from one armpit to another across his chest, coupled with a pair of jeans and a pair of white sneakers. It was a hideous sight—jeans and sneakers should never go along with blazers, Ashley thought to herself.

As for the diner itself, it went as awkward as one could expect.

It started with Shirley introducing the man. From the conversation, Ashley could gather that his name was either Anton or Antonio—one of those foreign names, but she was unable to follow the rest of the conversation as she was too wrapped up in the way he dressed.

At first, she thought her mother was trying to find her a boyfriend, but when he placed his hands upon Shirley’s… Lord, what a hideous sight! More hideous than his sense in fashion, or the lack thereof.

Antonio and I met in Athens … and then we were at this restaurant … he was being such a gentleman … yes, the yacht trip was splendid … did you see my tan, darling? Gotta do that more often …”

Ashley couldn’t pay attention to the conversation. She had too many questions in her mind, many of which were left unanswered.

Maybe he’s a nice guy after all … maybe she was too quick to judge, Ashley thought to herself. She might not agree with her mother’s decision, but if she was happy, why should it even matter? After all, she hadn’t seen her mother smile like that ever since her father passed away. Sure, there’s the age difference, but hey, they were both adults. They could figure that out.

But then Ashley noticed the first red flag. When it was time for the bill—thank god, thought Ashley—Antonio was eerily quiet. He was trying hard to blend in and engage in their conversations throughout the night, but when the bill actually came, he turned dead silent without uttering a single word.

She should talk to her mother about it

You know that he could be my brother or something right? Seriously mom?” Ashley asked Shirley as soon as they got back home. She just couldn’t help it.

“I’m getting old, kid, every moment counts. ‘Life is too short to be unhappy’—that’s what my yoga instructor keeps telling me,” Shirley responded.

“Hey, if you’re happy I’m happy, and you know that,” Ashley said. “But I’m afraid he’s in for the money. Remember your friend Rosie?”

“In for the money … I know. But at least he likes me—those eyes don’t lie. Some men just like older women, and I happened to find a good-looking one who likes me back,” Shirley said as she leaned her back on the couch.

And that was the end of that conversation

Ashley knew she needed to do something about it. She just couldn’t let her mother be manipulated like that. It’s an age-old tale—a young spouse marrying a wealthy, often a much older widow or widower, luring them with their youth and fiddling with their insecurities, only for them to pass away under mysterious circumstances shortly after …

She decided to give Kate a call and asked her for her opinion because that’s what best friends are for—to call them whenever the need arises so that you can complain about your mother’s new boyfriend and potentially stepfather who also happens to be alarmingly young.

“Hey, are you free now?” Ashley asked.

“Sure. Sup?” said Kate.

“It’s about my mom. She got a new boyfriend.”

“That’s nice. It’s about time she finds someone new, you know.”

But his age … I think he’s way too young for her.”

“How old is he?”

“29. Just a few years older than me.”

“Well … it is a bit too young.”

Ashley then proceeded to tell Kate about the dinner, the way he dressed and the way he behaved, and above all, her concerns regarding his intentions.

After listening to Ashley’s extended explanation of the night, with much emphasis on the way he dressed and the way he touched his mother’s hand … a scene that Kate tried to erase from her memory, she finally responded.

So what’re you gonna do about it?” she asked

“I don’t know. Maybe we can test him out? You know, see if he actually likes my mother?” Ashley responded. A momentary lapse of silence then ensued. “I have a strange idea—but I’m not sure if it’s gonna work,” Ashley finally continued

What do you have in mind?”

“Maybe you can try and flirt with him? You don’t have to commit to it of course, just … you know, basic flirting?”

“You sure it’s a good idea? I don’t mind but … you know, it’s your mom after all.”

“It’s gonna be alright. We don’t have to go all-in, just some light flirting and see how he reacts to that.”

“So let’s invite him to the bar tomorrow and see how it goes?”


The next day, they found themselves at a wine bar. All four of them—Ashley, her mother, Kate, and Antonio.

It started out as awkward as Ashley and Kate would expect, but when Shirley went to the bathroom, Ashley decided to follow her—but not before giving Kate the go signal before walking towards the bathroom.

“So, what do you do?” Kate asked, shifting her body towards Antonio.

“Nothing much. I worked as a designer in Spain for a few years, then I moved to Athens,” he responded.

“Oh, that’s so cool! Can you show me your works?” she said, then she began to lean towards him with her hair dangling by his ears.

That’s so cool! Can you teach me how to do that thing where …” she began to whisper into Antonio’s ear, and he reciprocated kindly to her sensual gesture.

It stopped as soon as it began as Shirley and Ashley started walking back from the far corner of the bar. Luckily, they didn’t notice any of that, Kate thought to herself.

But that night, she received a message from Antonio, along with a very suggestive picture of himself in the bathroom. That was all she needed from him.

Meanwhile, Ashley and Kate sat in the living room after their night out, with yet another bottle of wine to wrap up the night. “What’re you gonna do with Antonio? Are you gonna marry him?” asked Ashley.

Maybe. I don’t see why not. It’d be easier for him to stay here anyway,” replied Shirley, taking a sip of wine as she said that. “The visa is getting trickier these days.”

“Give it some thought first. You don’t have to rush anything,” Ashley responded.

It was then when she received a message from Kate … a screenshot of Antonio’s message, rather. It was jaw-dropping, to say the least.

But how could she bring this up with her mother without hurting her feelings? She could tell that her mother actually liked the guy—to a degree at least. Though at the end of the day, she was yet to know how her mother truly felt … she was too young for that. She simply couldn’t fathom the loneliness that old age entails.

But she decided she had to be straight with Shirley.

Did you know he was flirting with Kate tonight? He even sent her a message just now,” Ashley finally relented and said it out loud. “He doesn’t care about you, mom.”

Ha, really? Show me,” Shirley responded, half-jokingly.

But when she actually saw the message she was aghast.

“Well, it isn’t the first time I’ve seen that part of his anyway,” Shirley finally responded after a brief moment of silence.

“Listen, mom, go out with him all you want—just don’t try and commit to that. You know I want you to be happy, but I don’t want you to get hurt either,” said Ashley.

“I know darling. I know. Thank you for letting me know. In case you’re still worried … no, I’m not gonna marry him,” she said. “Besides, I wouldn’t want you to live with the fact that … you know, seeing that part of your stepfather in a picture. I might not be a great mother, but I’m not that messed up,” Shirley continued, winking at Ashley as she said it.

They shared a toast as they concluded the evening, knowing that all was well after all.

What can we learn from this story?

Have faith in your kids. Sure, they might not be as experienced as you are, but that also means that they can see something you might not see.

Always communicate. We might like or dislike something, but it’s always better to be honest about it, to make sure others know how you actually feel.

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