Tag: dating

Misdialed Date

Chicago 2005.

It was a mid-summer day. The sky was as gray as a billionaire’s suit, and the sun refused to show its smile.

A pounding echoed through Amy’s apartment.
“One second,” Amy called, barely cracking open the door. Dressed in shorts and a t-shirt, she juggled the door knob and battled her rebel hair with her free hand.

“What are you doing here so early?” she squinted at the familiar face.
“Early? It’s almost eleven,” Dan replied, nudging the door open and striding in as if he owned the place. Clearly, he was no stranger to Amy’s apartment or her couch.

“Yeah, but do you remember how late you dropped me off last night? I went to bed at ‘this morning o’clock’.” Amy yawned, trailing Dan to the living room.

She peeked outside, noticing the sky screaming an overcast mess.
“This isn’t beach weather, is it?” Amy observed the trees bending in the wind like a morning yoga pose gone wrong.
“Nope. Looks like we’re not the only ones hungover. But we can do something else,” Dan suggested, already commandeering the remote.

“Coffee first. I need to wake up,” Amy declared, holding her index finger and heading to the kitchen.
“And maybe a bagel?” Dan called, settling into the couch like it was his living room.

“How’s George? He ended up driving Rita home, right?” Amy’s voice floated over the sound of brewing coffee.
“Did he? Man, he was smashed.” Dan flicked through channels.
“I hate when he drives like that,” Amy muttered. “The party was nuts, and George got totally wrecked.”
“Good for him. First big night since his breakup,” Dan replied.
“I know. After everything with his ex…” She paused, considering a thought.

“Do you think he hit it off with Rita?”
“What?” Dan’s eyes were glued to the TV.
“Maybe he’s still at Rita’s?” Amy teased, walking back with two steaming cups of coffee.
“You think they… no way. They just met,” Dan scoffed, accepting his cup.
“I don’t know, I got a vibe,” Amy smirked, pulling out her Motorola flip-phone. “Let’s see.”

She dialed, putting on her best ‘Rita’ voice.
“Hi George, did I wake you? Just wanted to thank you for last night…” Dan’s eyebrow arched in surprise as he listened to Amy’s voice, a perfect imitation of Rita’s, turning more flirtatious with every word.

“Are you busy tonight?” There was a long pause. George talked while Amy was nodding.
“We should totally go rollerblading later.” Amy winked at Dan, who was watching her with his jaw wide open. “Great. Pick me up at 5.” A short pause. “Okay, see you then.”

Dan nearly spit his coffee.
“He can’t think you’re actually Rita, can he?” Amy hung up, a mischievous glint in her eyes. “He’s got a rollerblading date with ‘Rita’ at 5 tonight.”
“No way. He fell for it?” Dan laughed loud and hard, disbelief coloring his tone. “This is gold!”

*

George parked his Altima outside a modest single-story house, the smallest on the block, with a well-tended lawn surrounding it. He checked his hair in the rearview mirror and headed for the door.

It was exactly 5 o’clock. He rang the bell and waited with anticipation.
“Hi,” Rita greeted him, not stepping aside to let him in.
“Hi, ready for rollerblading?” George asked, his body shifting nervously from one foot to another.
“Rollerblading?” Rita looked puzzled. “No, I can’t. I’ve got other plans. You should have called earlier…”

George’s face fell as he stood awkwardly at her doorstep, mixed feelings swirling within him.

Both stared at each other in silence for a moment. Something was off.
“But you called me about it this morning…”
“I didn’t call you today at all,” Rita frowned.
Flustered, George apologized and retreated to his car. What else could he do? His anticipation dissolved into a confusing blend of disappointment and embarrassment.

He was about to start his car when his phone rang.
“Rollerblading, huh?” Amy teased.

George groaned.
“It was you? I thought Emily set me up.”
“Nope, all me. Sorry, George, I got carried away. I owe you a big apology—I’ve gone too far.” Amy’s voice softened, yet she struggled to stop laughing. “I can’t believe you fell for this!”

George shook his head, even though Amy couldn’t see him.

“Come over, I’m ordering pizza,” Amy added.
George sighed. He couldn’t decide whether he should scream with anger or laugh. He put the key in the ignition and drove off.

Amy and Dan couldn’t stop cracking up as they awaited George’s arrival to clear the air and get a full story.

“You two watch out; just wait for my comeback,” George grumbled as he walked in. “I’m warning you. You have no idea what is coming at you,” he announced, unable to suppress a smile at the absurdity of it all. “I mean it.”

“Good to see you without your rollerblades,” quipped Amy, extending her arms to hug George. “Please, don’t be mad at me.”

“You ordered pizza; I brought beer,” said George with a smile, closing the door behind.

Author’s Note:
Meet the real Amy and George—they are actual people. In fact, I’m Amy, and George is my friend Matt. This is the only picture I could find of us from many years ago. We are standing in water, awaiting alligators (at least that’s what the tour guide told us). What you don’t see is the boat on the other side, filled with a bunch of ‘chickens’ too scared to step out, including Dan, who took this picture. And finally, yes, I really did set up that rollerblading prank date. 🙂

How to Determine if She’s Single: A Gentleman’s Guide

Imagine this: you’re at a cozy coffee shop, exchanging glances with an intriguing stranger. There is something about her—the way she smiles into her book or holds her mug— that quickens your pulse. Tempted to approach, you hesitate… There is one burning question holding you back: is she available?

Not long ago, a guy in a gym approached me with an intrusive yet direct question: “So, are you single?” Although I admired his boldness, I must admit that given our previously limited interaction, the abrupt bluntness of his question caught me off guard. At the same time, it made me wonder, “Could there have been a better, perhaps more accurate, way to approach this?” Indeed, there might be a more nuanced strategy worth considering. So, how should one investigate a girl’s relationship status in a respectful manner? Let’s delve into that.

First and foremost, asking such a personal question directly signals your interest in her. Is that truly your intention? While showing interest is perfectly fine, it’s often better to establish some level of acquaintance first. Avoid diving into personal questions too quickly; if she finds you approachable or attractive, you already have an advantage. She will be more likely to engage openly in conversation. However, if she perceives you as unappealing, if she’s shy, or simply lost in her thoughts—as I often am—a subtler approach is advisable. Start by establishing a basic connection; exchange a few sentences to ensure she doesn’t feel threatened or intimidated. If you immediately start with personal inquiries, she might think you are only after one thing. If a more meaningful relationship is what you’re after, taking the time to get to know each other—even through a brief conversation—can naturally lead to discovering shared interests and, perhaps, whether she is interested in you too.

Next, don’t assume she will truthfully answer your questions just because you asked sincerely—it’s always a gamble. Even if she is unattached, she might dodge the “are you single” question to maintain boundaries and, sadly, get rid of you! Don’t cut yourself off prematurely. Engage in a little chat, listen attentively, and observe subtle cues. Some women may casually mention their relationship status during discussions. Others like to boast about their boyfriends, signaling disinterest in other guys. Be attentive, and you might glean valuable insights about her life and preferences. Also, be cautious and don’t overwhelm her with too many personal questions. I hate that! It’s so invasive! I believe most girls would agree with me, so it’s wise to limit yourself to one or two questions per encounter.

Another scenario to consider: What if she’s in a “crappy” relationship? What if her saying, “I am not single,” doesn’t tell the whole story? She might be somewhat “tied” to someone but physically and emotionally disconnected, perhaps awaiting a way out. In that case, you, dear reader, might unwittingly become her ticket out! But be careful; you could end up being just a “rebound guy.”

Men often step back when they discover a woman is taken. I find it classy and respectful. However, let’s not assume all relationships are strong and fulfilling. Many women find themselves in relationships that aren’t harmful but are far from healthy or ideal so, it’s not always urgent to leave. See what I mean? It’s impossible to break something that’s already broken. Rather than disrupting, you could play a constructive role in a relationship that’s already unstable or dysfunctional.

Ultimately, if your feelings for a girl are genuine, why not pursue them? If your heart or gut, tells you there is something there, then why not explore it further? It may be worth the risk. Stop anticipating and chewing on your fingernails. Make a move! Girls appreciate confidence in a partner! I, for one, value assertiveness and support. Don’t give up too easily; let her get to know you. Show her your authentic self over time, and allow the connection to develop naturally. Don’t be embarrassed to show your vulnerability—it isn’t weakness; it’s a sign of humanity. Girls like to feel needed too, so let us take care of you. Let her see that you’re willing to invest in something meaningful.

I believe that a strong and healthy relationship can withstand any challenges. If a girl (or a guy for that matter) is truly committed, nothing can break that bond.

But, what if she is absolutely not interested? Then you thank her for her time and move on. Remember, you do not know her feelings and intentions until she clearly and unequivocally communicates them to you. Don’t make incorrect assumptions. Nonetheless, if she says “no,” you will still live, and you will be just fine.

In summary, if you feel compelled to ask about relationship status, do so with tact and respect for her boundaries. Rather than a blunt “Are you single?” consider a more delicate approach. You could express interest in getting to know her better and ask if she’s open to meeting up sometime. This approach not only allows for a more natural progression of the conversation but also demonstrates your genuine interest in her as a person, regardless of her relationship status.

Returning to my story, can you guess how I responded to the guy? If you get it right, I’ll buy you a coffee! 😉